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Charlie O' Donnell

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Monday, May 11, 2020 - 9:37am

VCs are notorious for kicking tires.

VCs take a meeting just to learn about an area. If deal flow is slow, a VC will take a meeting if you and your team seem mildly interesting even if your product isn’t. Sometimes, if you seem well connected to other founders or VCs, that will get you a meeting—because you don’t want to miss something everyone else has seen.

Some later stage funds will take a meeting long before they ever plan on writing a check with the promise of “opportunistic” seed investments (to the guy or girl they went to grad school with). Some VCs have no money left in their funds, but they still like playing VC.

You could complain about this as bad VC behavior, because wasting a founder’s time is a mortal sin in Startupland, but I wonder why we’re letting founders completely off the hook in this process.


If you had a salesperson and they spent all of their time with inbound leads that didn’t pay off, you’d have to let them go. The ability to qualify a lead and spend time in your pipeline commensurate with the likelihood of payoff is a critical skill.

Or, you could blame the leads.

Fundraising is a sales process for shares in the company.

Is it the lead’s problem that they aren’t serious buyers? A great salesperson would figure that out right away—and qualifying your fundraising pipeline is a critical skill for a good fundraiser.

So how do you qualify a VC in your fundraising pipeline?

Ask Pointed, Specific Questions

Do you lead?

Do you have dry powder for this? How much?

Do you have the bandwidth to work on this?

Do you see a reason to turn this down right now?

What do you feel you need to be convinced?

What do you feel you need to convince others in your firm?

I believe X, Y and Z key things that cause me to believe in a big outcome. Do you agree with all three? Do you think the outcome could be as specifically big as I do?

What work will you do next to either convince yourself to do this or not to do this?

When can I expect this will happen?

If you walk out of a meeting and you don’t know anything more than “They thought it was interesting…” then you didn’t ask enough about where they were at on this.

Manage Your Time

Control the time and structure of the meeting.

Have a plan for what you want them to know—have questions to make sure they understood it and come to next steps that either move them forward in a process or off the potentials list. Use some old school sales tactics like, “I’m going to use this first ten minutes to determine whether this is a fit—would you be willing to give me back my time if you determine right away that it isn’t? I have plenty of calls and e-mails to make and would appreciate a quick wrap up if you’re not interested to hear more after that time.”

Seniority Within the Firm

Some non-partners at a firm can lead a deal—but the reality is that if you’re scoring your VC leads on likelihood fo close, you have to take points off for junior VCs or partners who probably have less pull. The partner who just got promoted from principal undoubtedly will have a lower close rate than the partner whose name is in the door or who founded the firm.

That’s not to say you shouldn’t pitch people besides the most powerful partner that everyone else is probably pitching—you just have to be careful you’re not leaving yourself open to being disappointed at the finish line because they didn’t have the internal pull to get it through the partner meeting.

Circumstances of the Meeting

Did they feel obligated to take the meeting because of an intro or do they have a stated interest in the space—or even better, did they tell you specifically why they’re interested in your company?

Scheduling and Cadence

An interested VC won’t wait a week or two when a round is in process to meet. They’ll get back to you right away without you prompting it. They’ll even introduce you to others in the firm before you walk out the door. If you feel like you’re pushing the deal forward, your chance of closing are defiantly lower.

Researching the Space

Ideally, the investor either already knows what they’re looking for or you’ve so clearly articulated the opportunity that they don’t need to take time to get up to speed on the space—or, you’re so clearly the expert team that they trust you know what you’re doing. Anyone who has to start from scratch on a space isn’t your most likely next close.

Lack of Vigorous Agreement or Disagreement

If a VC has strong opinions, you can have a back and forth. If they’re just not engaging at all, there’s a good chance you’re looking at a pocket veto.

A pipeline should feel active—a living, breathing organism with flow and movement, not a sack you’re dragging up a hill. Remember, there is way more money out there than good ideas—so if they’re not chasing you, you probably haven’t done the job of being convincing.

If you can’t get a read on VCs at all, you may want to check out, where you can get aggregated and consistent feedback from an anonymous panel of venture investors.

Do you have your own suggestion?

Retweet this post here and add your own!

Monday, April 13, 2020 - 11:38am

Obviously, the fight against Coronavirus has not stopped, but it’s hard not to look ahead to what’s next. How will having the world on lockdown affect our society in the long run?

Here are a few trends I think we’ll see going forward:

1) Work from home is here to stay—at least partially.

Absent the additional, albeit temporary, task of having to educate your own kids while at home, many people have reported being a lot more focused and productive while out of the office—not to mention the two hours a day they’re getting back. While some people report actually missing their commute—and the act of seeing new strangers every day—it wouldn’t be surprising to me if everyone who formally worked in an office does at least a day or two out of the house going forward. That’s going to significantly alter the way offices will be set up, making them less about personal space, featuring more flexible storage, and more adaptable to different groups of people coming in every day.

2) Video connections are here to stay.

Video chat isn’t new—but the concept has now been “microwaved”**—heated up for just long enough to reach that optimal temperature for mass consumption. Whereas it previously felt like a bit of a fringe use or even a bit of awkward overkill, I think now we’re once again seeing the value of faces and live human expression in our digital communication.

Expect video calls to replace audio conference calls permanently and for use cases like video dating and doctors visits to become more of the norm, especially as people grapple with the lingering societal effects of coronavirus pre-vaccine. People need more data on the quality of a connection to decide whether going outside for a stranger is worth it.

3) American voters move left on domestic issues.

Healthcare for all. Worker protections. Teacher pay.

So many policy shortcomings that left far to many people who are keeping our country running vulnerable or unappreciated are sure to be addressed in the next few years. Joe Biden may not have been as left as many were hoping—but he’s sure to be forced left by masses of people left very exposed and in need of government assistance during this pandemic.

4) American foreign policy to shift towards nationalism.

I forget who is supposed to be on what side of globalism these days—whether or not free trade is a Republican thing or a Democrat thing, but it doesn’t matter now. Expect borders to get tighter and critical manufacturing to get domesticated—because what definitely didn’t happen was the world as a whole coming together to solve this crisis. Every country seemed to retrench into fending for itself, with very little cooperation, undoubtedly costing lives. Many politicians seized upon globalization and “foreign invaders” as a scapegoat for their own shortcomings in responsiveness—but the crisis did lay bare a lot of issues with a just in time global supply chain.

5) Privacy and security under siege.

Google and Apple are going to help the authorities figure out where you’ve been and who you’ve come into contact with for the “greater good” of society.

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We used to think of certain aspects of our data, like our health status, as private information. Just wait until you need to get your temperature taken to walk into an office building.

I’m not saying that’s a bad idea—but it’s a very scary slippery slope.

6) Universities are effed.

Scott Galloway wrote the take on this here but sufficed to say that if you’re not a top tier university, your days were probably numbered anyway. Going into a recession, a lot more students are going to reconsider whether mortgaging their life really makes sense economically in a world where online education has become the norm.

7) Working out from home—will be temporary for most people.

Home workouts, this may surprise you, aren’t new. Jane Fonda’s home workout VHS sold 17 million copies in the 1980’s—compare that to less than a million Pelotons currently in circulation. Sure, this quarantine is going to be a huge sales boost to connected fitness products and Peloton seems like the clear winner, but most urban dwellers will find that the gym experience is superior to turning their tiny studio apartment into a home gym. Not only that, but home workouts aren’t particularly social and classes are too much of a water cooler experience to completely go away. The quarantine may get more people working out who didn’t before, but don’t expect the boutique fitness gym trend to end anytime soon. Think of this as just a delayed defeat of New Year’s Resolutions.

8) Peak City.

New York City quickly turned into a ghost town during the quarantine. Those who could escape to family or second homes did—and quickly found that the suburbs weren’t actually that bad of a place to live. With the rising cost of urban housing and the limited space for kids, I think you’re going to see a serious migration of families, especially those with jobs that could work from home at least partially, into the burbs. Part of this will be driven by space issues, but also I think in times of crisis, families come together. Anyone who grew up in the burbs that could work from home is seriously considering going back right now—especially when it comes to issues like childcare and eldercare. With the rising costs of both and the aging of the Boomer population, a lot of people are realizing that life is more manageable when extended families are closer together.

This will also continue the trend of turning purple suburbs blue. As Democratic urban dwellers head home, the shift of the suburbs left because of healthcare and gun control will only continue.

9) The Loosening Grip on Real Estate

Imagine this thought experiment. What if we decided that the Native Americans had it right—and that “ownership” of land didn’t make any sense any more than ownership of air and water. Imagine all of the land was essentially put in a public trust, and if you wanted to use it, you could, but you paid rent into it.

If we were all renters now, essentially renting from each other, we could all put our rent and overall housing costs on hold, instead of worrying about crashing the whole economic system. Pausing evictions are only going to be the tip of the sword in a world where everyone at the same time asks for a break. How long before WeWork tenants unionize, forcing a landlord already teetering on the verge of bankruptcy to come to the table for relief? Tenant associations are going to get a major leg up post-coronavirus and into this recession and landlords will have to contend with a new economic normal.

10) New and improved kids.

Kids kind of like doing the opposite—so when you force them in front of a screen all day for school and tell them they can’t go out and play with their friends, all they’re going to want to do is go outside and play with their friends instead of more screen time.

Even if your kid does have an increase in overall screen time, there are still large swaths of the day that need filling—and kids are going to have to become a bit more creative to entertain themselves. Passive consumption of media is going to get replaced by large scale in person organization and coordination of family TikToks—where the creation is just as fun as the viewing. Kids are getting much closer to their families as their main source of connection and entertainment during this time—and more parents are appreciating what it means to be home for dinner. Some of those meals, in fact, are under kid supervision. I’ve now been on several virtual networking lunches where parents were eating lunches made by their kids who probably learned their way around the kitchen on Youtube or TikTok.

Expect to see a lot of positive trends coming out of this for kids—an appreciation for being outside, more connections to extended family, and increased creativity. Couch fort construction is definitely on the rise.

What are your predictions for #postcoronatrends? Post this article and hashtag on social media with any additions you’d like to share.


Wednesday, April 1, 2020 - 5:40pm

Let’s establish two things right off the bat:

One, the Coronavirus Pandemic is a global tragedy that has already cost us far too many lives and create economic devastation.

Two, if you are lucky, you are still being paid to do a job—a job that, for founders, marketers and sales teams, means connecting with customers during a terrible health crisis and a recession.

What’s a company to do with their marketing?

I think you have to make the assumption that, at some point, we get back to a more normal work routine in a matter of months, not years. If you can’t assume that and you don’t work for Zoom, you should be liquidating all your assets, finding a piece of land in the middle of nowhere with an internet connection, and learning how to live off the land.

So what are you supposed to do in the meantime? Does it look tone deaf to be out marketing your business right now?

There’s certainly a right way and a wrong way to do this—and I would say that, actually, companies have three important factors in their favor right now:

1) Many of your customers have more hours in their day now. Business has maybe slowed and they no longer have two hours of commuting. Plus, there are many examples of people actually working more hours because there’s not much else to do. (This is, of course, if you do not have kids to suddenly homeschool—but only 40% of American households have children under 18, and the teens are off somewhere around the house on TikTok anyway.)

2) The dramatic shift in our day to day life has forced everyone into unfamiliar territory. Everyone is looking for answers.

3) Screen time is off the charts right now.

The combination of all of these factors creates an opportunity for companies to provide information and thought leadership during a difficult time—or even simply entertainment. If you can do that, you’re going to generate a lot of goodwill—and leads—that will benefit you as budgets start to open up again and things get back to normal.

If you aren’t selling right now, generating leads and cultivating trust through content, especially video content, is really your only option. Channels meant for conversion, while cheaper right now, might not work for weeks or even a couple of months.

But how do you do that if you weren’t setup for that to start with?

Here are some tips:

1. Start with the customer in mind first—ask what content you would want to consume if you were them. What do they need?

If you’re selling to small businesses, creating channels of content that explain various grant and loan programs would be super helpful—I don’t care if you sell point of sale software for restaurants. You’re now in the financial education business for the next few months. Start bringing that content that provides recommendations on how to do right by your employees and to be honest about difficult communications.

If you’re selling food online, don’t just sell food—teach people how to cook who may have never done it before. Your streams should look like a cooking channel right now—and I’d argue that’s probably what you should have been doing beforehand anyway.

If you’re a Presidential Campaign, make all of your channels a 24/7 science and fact-based news org right now that also salutes heroes and tells the stories of people on the front lines—in direct opposition to the self-aggrandizing cloud of spin we’re seeing from your eventual opponent.

Are you a travel company? Ask your customers to send you videos of their favorite places and some audio for you to string together in a sit back travel show so you can take advantage of the likey post-quarantine spike in trips because people can’t wait to get out of their houses.

Moreover, go meta and create online content that helps your customers create online content! Like you, they’re also struggling with how to sell their customers, so just leveling with them as a peer on what you’ve learned can be super valuable to them.

2. Accept different levels of production quality—sometimes, but not always.

You may not have access to a whole video editing team and you’re undoubtedly going to start off your webinar with “Can everyone hear me?” while your kids go running across the back of the room.

That’s totally fine.

That being said, please stop using Google Hangouts to do anything professional. It doesn’t work nearly as well as Zoom. Pay for a Zoom account. It’s worth it—but also take the time to understand the controls. Learn the difference between a meeting and a webinar, and make sure your settings don’t open yourself up Zoombombing (look it up).

Also, if you’re going to shoot a video remotely for content purposes, you don’t need to get stuck with conference call chat level video quality. You can use tools like Openreel (BBV portfolio co) to remotely operate the other person’s phone and upload HD back to you to take advantage of the HD level camera they paid up for when they got their iPhone in the first place. (Check these examples out.)

3. Be ambitious.

A lot of top people you might not have access to otherwise might have some time on their hands. Recently, I tried to think of the two very best people I could imagine would have great advice for startups facing a potential venture downturn. While a lot of other people have been doing “Ask a VC” sessions about how to dal with this, the reality is that there are only a handful of VCs who were still active during the Dot Com bust and know firsthand what that was like. Asking someone who has five years of experience in venture what companies should do is a bit ridiculous.

I was able to get Brad Feld and Todd Dagres to sit for an interview—two VCs with about twenty five years of experience in venture each. Neither is in NYC and so actually, doing something virtual worked out great—and we had over 330 live viewers for a whole hour, plus at least that many who watched after.

Go out and get the “big ask” for your audience—because they might not have a lot of other things to do with their time. Also, if you’re doing content meant to help your audience through a difficult period, they’re probably glad to do it.

4. Plan for recurrence.

Sometimes, it’s easier to plan to do a dozen of something and commit to it than it is to do one. It changes the level of tolerance you have around perfection, and it commits you to learning and improving as you go along. Instead of just trying one episode of a 90 second stress reduction tips clip for your meditation company, plan for a dozen. Plan daily clips. Maybe it winds up being the 6th one that goes viral for whatever reason.

5. Break the content free.

Every professional in the country right now has Zoom on their computer. You cannot avoid it.

So, if you’re producing content as part of your business that lives in an app, it needs to come out onto Zoom or the web in some way. People aren’t “on the go” the way they normally are with phones—they’re sitting in front of web connected TVs and on couches with laptops. Getting someone to convert to an app is probably even harder now when so much is a click away on their laptop.

So what’s your Zoom content strategy?

Zoom can be a great lead generator. Collect all the e-mails and mobile numbers you can for reminders, follow-ups and invites to future events—even if you have to cludge it all together pretty manually because Zoom isn’t a real marketing platform.

Every single company that needs leads should be offering webinars and other content on Zoom or other web based platforms right now, period. Why? Because it’s something people are used to, it’s on their desktop, and the aspect of making time for something and being allowed to ask questions on the platform creates a higher order of engagement. If I have to download your app to get your content, you’ve failed. Make it easy to get the content, then send me the link to your app.

If your customers need video advice right now, even if you normally sell printers, setting up a daily video production Q&A may make you a #quarantinehero during these difficult times, and I believe that will pay off when people need to go back to the office and buy a printer.

Or, just find the heroes already in your network. Who uses your product? Parents, teachers, doctors, nurses. Tell their stories using remote recording platforms like Openreel.

Just make sure that everything you do starts with the genuine interests and needs of customers. It’s ok and appropriate to acknowledge what’s going on around us, but also don’t make it the central aspect of your marketing pitches. I have a whole inbox full of people who are professional contacts of mine, who are probably on my newsletter and social feeds hoping that my family is ok, yet when my mom died a few months ago, I never heard from any of these people—so, sometimes the family concern repetition kinda rings a bit hollow.

Helping someone tackle their real professional responsibilities and acknowledging that it’s a difficult time to do so will never ring hollow.

Monday, March 23, 2020 - 10:39am

I remember looking at other people on the street the day after 9/11. Everyone was just so sad. It was a shared moment in time where nothing needed to be said, and all we could muster was a slight nod to acknowledge that what you were feeling, everyone else was feeling, too.

It felt like things would never be the same.

Yet, it wasn’t very long after before I was on a plane. Sure, I was a bit apprehensive, but slowly it faded away. I don’t know when we stopped thinking that every loud noise was a terrorist bomb, but we did. We said we’d never forget, but, in all honesty, we kind of did.

Absent of the security theater we now have at airports and office buildings, not much about the lives of most people in this country permanently changed. We tragically lost thousands of troops and needlessly spent trillions on endless war, and I’m sure those who were at Ground Zero or who lost colleagues wouldn’t forget, but Joe and Jane America moved on.

The Financial Crisis of 2008 sure seemed bad in the moment as well. People lost homes and businesses—banks blew up—but then we went on an 11-year bull market run that sent unemployment down to historic lows.

There we were at the casino table again after that, pouring billions of dollars into unprofitable startups while cutting taxes when we didn’t need to, for people and companies who didn’t need it, with little regard to the future.

Some sovereign wealth funds lost their shirts and some startup employees had their options fall underwater when the likes of WeWork blew up, but somehow we collectively dodged serious pain again.

I don’t think it’s going to be so easy to move on this time. I think the impact is going to be greater than we imagine—to the point where we will look back at our generation and we will be defined by this moment, much the same way we had a “Depression-Era” generation.

I don’t necessarily mean that this is my prediction as to what the stock market will do or what this might mean for startup returns.

We’ve already been in an economy where the stock market doesn’t reflect how the average person is doing. Similarly, startup returns haven’t necessarily reflected our ability to create meaningful and lasting new businesses either. Investors have been making a bunch of money cashing out of companies that might not have lasted another year even before Coronavirus hit.

I think we’re going to see such far-reaching ripple effects not only in the economy but in our own psychology that we’re going to approach everything differently.

Take Uber, for example—one of the largest wealth creation events of our time. It’s a status symbol and a calling card to say you were an early investor, despite the fact that the company that still loses a ton of money. It was built on a network of drivers woefully unprotected by labor laws, without healthcare, wage production or unemployment benefits—the consequences of which are now painfully all too obvious and should seem a little less like a source of pride.

I don’t think building companies like this are going to be seen the same way going forward. The US taxpayer will have to backstop the company’s lack of basic support for its workers, much the same way it’s been doing for Walmart for years.

Scrutiny is coming in a big way.

As I write this, Congress is working hard to undo the mistakes of the 2008 bailout and the sense that corporations got off easy and the little guy was never made whole. They’re debating restrictions on stock buybacks, direct payouts to individuals—and confronting the hard choices of choosing whether or not we have enough money to bail out both small business and the cruise lines.

If I was in the cruise line industry—I’d be polishing off my resume right now, because I think that ship has sailed.

We aren’t going to be able to fix everything.

Faced with a health threat and choosing between taking sick leave and paying your rent, I think the country is going to take a dramatic turn left—realizing that no one should have to make those decisions.

Some people have been riding high on the horse for too long.

The window on gutting ACA will be closed. Anyone who threatened it will be voted out along with the congresspeople who dumped stock while telling the public the Coronavirus was going to blow over.

The era of the little guy getting the short end of the stick is over.


Because so many people are going to directly feel the pain. Few people are feeling secure in their job right now, and save for a few morons on Florida beaches, most rational people are concerned about their health and the health of their loved ones.

They’re feeling the direct effects of a fragile economic system and an underprepared health system, run by an incompetent administration. I’m not making this political—no objective person could possibly give the White House passing grades on its Coronavirus response. Start from the firing of the National Security team’s epidemic response experts to the continued misinformation that has to be corrected and backtracked after every press conference and I think the story of our national nightmare comes to a close soon.

You have to go back to the Depression and World War II to find a disruption of this magnitude—and that shaped an entire generation.

This will definitely be a generation shaping event—one in which we’re going to undergo a lot of pain and difficulty, but ultimately, for the better.

I don’t see us building new companies that exploit workers in the same way as the past.

I think we’re going to shore up our economic system—making it a safer place to be for individuals and small businesses. Perhaps this comes at the expense of those at the top, but ultimately I think it will be a system that can drive growth from the bottom up through greater access to education and a more competitive playing field.

I think we’ll be more likely to see through hollow promises of demagogue leaders unfit for the moment in the future—because we’re seeing firsthand the destruction that incompetence breeds.

How we run businesses will be different, too. I’ve written before about the profiles of leaders we’ll be looking for. This feels like a turning point moment for the leadership style of female founders who focus as much on making sure things don’t fall apart as they do on how big they can get something to grow. The remote chance that things can fall apart won’t feel so remote.

There are some lessons on how this all plays out that we can learn from the past. I know it’s going to be very difficult for a lot of people who will undoubtedly have to rely on government and other kinds of assistance—just as it was for my great grandfather who lost his grocery store on Monroe Street on the Lower East Side. He never really recovered emotionally from that loss of pride.

A lot of kids are going to grow up sharing rooms and families are going to move in together, just as they did when my grandparents took in other families into their house. I’m not totally sure that’s going to be so bad. I think we’re realizing now as families return home during this crisis that we may have gotten a little too far away from each other.

This is going to be a more difficult economy, but I believe it will be a more collaborative one. We’re going to have to do more with less. We’re going to need the government’s help along the way, and it’s going to need our help in steering it where it can help the most.

Our Green New Deal will come—if for no other reason than doing more with less is going to mean less material, more reusability, and less footprint, for economic reasons and supply chain shortages. Hopefully, we can be a little more innovative with material reuse than my mom cutting up her parent’s basement carpet to cover the holes in her shoes as a kid.

Harder for many, but better for all of us will be the new economy that Il look forward to being a first check investor in.

Monday, March 16, 2020 - 6:38pm

As a seed stage investor, I know the math. Half the companies I invest in won’t provide a financial return. Another forty percent or so will go sideways a bit, and the last ten percent will drive most of the gains for my investors.

Leveraging up a company with venture dollars in an attempt to grow to a national or world class brand can be a risky proposition. You wind up taking on added complexity, and you’ll be asked to do a bunch of things right that you’ve never done before, all at the same time.

Some losses sting more than others, even if each of them individually don’t represent a significant chunk of a larger portfolio that is doing well. Everyone who follows me knows the love I have for Ample Hills, their product and their wonderful and hardworking amployees.

Five years ago, I met and backed Brian and Jackie from Ample Hills as they were building one of the most beloved young food brands ever seen. Everything was going right for them—they had a burgeoning deal with Disney to not only get a space at Disney World, but also to license Mickey and Marvel for new ice cream flavors. Prime locations were beating down their door for expansion.

They were capacity constrained from a production standpoint, but it seemed like a good problem to have. They decided to raise venture capital money in order to build a factory, open new stores, and take advantage of their newfound fame to go into wholesale.

Along the way, each undertaking proved more complex than expected. Shop openings were delayed for reasons ranging from unexpected asbestos that needed to be removed to delays in the opening of buildings we were located in. We tried selling fun new square pints—memorable and meant for sharing, with two scoops under the lid—but the square pint filling machine never quite worked as intended, despite promises from the manufacturer.

Eventually, we got past these bumps—getting smarter about leases, more streamlined from a labor perspective in our shops, and more focused after spending lots of time on our Disney relationship and other new initiatives, the factory itself turned out to be a lot more overhead than the business was ready to handle. It was too big and too expensive to run given the size of our business and speed of our new shop openings.

The factory was eating cash faster than our customers were eating our ice cream—and they were eating a lot. Some investors bailed at the last minute because (we believe) they had experienced real estate losses elsewhere.

We couldn’t fix the factory situation in time and before we ran out of cash. Part of it was that we had gotten over our skis on valuation, making further investment unattractive to both new and existing investors. Some key existings who didn’t want to see their prior money get lost wouldn’t budge on a dilutive financing, despite the fact that they knew where we were headed. This is what happens when you deal with investors that aren’t professionals.

The answer, unfortunately, was to declare bankruptcy. It was a last resort that means that existing investors will get wiped out and some partners the company owes money to will not get paid, which is a devastating thing for the founders who have always been generous partners to the larger community around them.

That doesn’t mean Ample Hills is going away—we hope. It just means that it has begun the process of looking for a new owner and without the burden of an expensive factory. The business will be much simpler, focused on our strength—the growing revenues and customer loyalty at our shops, which are profitable when you subtract the costly overhead of a big factory.

Over the past year, I watched Brian, Jackie and their team put in the maximum effort through an incredibly difficult situation. One day, there will be a book on everything they went through—but for now, they’re focused on keeping the brand and product, still one of the most beloved in the food world, alive.

They’re in the process of talking to some buyers and open to speaking with others who share their vision of a national brand with local familiarity, friendliness, and a ton of human joy per square foot.

If you are a turnaround, bankruptcy or private equity investor and have questions about the sale process, you can e-mail me at

I hope one day in the future when we get out of our homes to meet you all at a nearby Ample Hills, having put this difficult chapter a long way back in the rear view mirror.

Monday, February 24, 2020 - 12:40pm

The answer is easier than you thought: Anything you want.

No, seriously—that’s the perk of running your own business. You select your salary.

Now, if you want to have investors and potentially maximize growth for the company, that’s a different story. Investors are going to want their investment dollars to be going towards growth than going directly into your pocket—but what does that mean for how much you can actually pay yourself.

If founder salaries are supposed to be no more than some set number, how does that work if a founder is a single mom with three kids and a mortgage. Clearly, they need more to live on than a 22 year old that is still living at home.

This is a great example of how what you’ve heard out there in the ecosystem probably isn’t true—and it’s most likely based on someone’s idea or company not being interesting enough for investors.

For example, if Katrina Lake, the founder of Stitch Fix, went off to start a new company, pretty much any investor would give her a blank check to do it.

What if she built a cashflow model that said her seed round gave her more than enough capital to blow through what most people would agree were Series A goals—but that included paying herself $250k a year.

Would you walk as an investor? Honestly, you’d be an idiot to—and she wouldn’t have any trouble raising even with this high salary.

Katrina is a rich woman. The idea that somehow squeezing her on salary as an “incentive” would be moronic. Frankly, I don’t really believe in most “skin in the game” arguments. The vast majority of startups are started by people who would have absolutely no problem getting a job elsewhere. Do you think the average straight white male Harvard MBA who can code or whatever is only working hard on this startup because of his equity to salary ratio?

On the other hand, do you think that same number is the primary motivating factor for the black female founder, weather she, too, went to Harvard and can code or not. I tend to think she’s going to have plenty of added motivation regardless of her comp.

What this should really come down to is a financial model. In most angel or seed funded companies, increased founder comp adds risk—because the company really doesn’t have a lot of “extra” capital to go around. The company probably has just enough runway to make it to a potential next round, not leaving a lot of room for any mistakes or mishaps, of which you know there are going to be some.

That’s why most investors balk at high founder salaries—because it feels like until the company starts making some real money or is seriously de-risked in some way, you’re adding additional risk that they don’t need to take. There’s some other deal they could invest in that has a much better chance of hitting its goals.

Now, if you want to make the argument that your company is de-risked because you’re a better founder than that 22 year old, so you should be paid more, I understand, but there are plenty of very smart senior people who have started companies that have failed. Your experience is probably the reason why you’re being backed in the first place—but once you get backed, in my experience, everyone’s pretty much starting out with a similar risk profile.

In other words, starting from scratch is very hard—for everyone.

Still, you’re looking for a number and I haven’t given you one yet. What I can tell you is that most founders in a seed round tend to max out around $120k in NYC. I haven’t seen more than that too often—and if that’s what it was, I wouldn’t ask any questions around why.

If that’s not a number that works for you, I would be more than happy to hear why.

Let’s say your situation of having kids in good private schools, an elderly parent at home and being the sole breadwinner as well as the payer down of medical school debt means your number needs to be $170k, or even $200k. You walk through your numbers and yup, you just happen to have a really high overhead.

Does that mean you can’t be a founder?

It shouldn’t at all—but, what I think investors would want to see is that your plan gives the company more than enough runway to hit its goals.

Few companies really ever failed or succeeded because of an extra $50-100k over the course of a year or two—but if you want to change the perception of the risk vs. return, here are a few things you can do:

  1. Raise a bit more money at a slightly lower valuation. If your 18 month plan calls for raising $1mm, raise $1.5mm at the same valuation. This way, you’re eating the cost of your own additional budget by selling more of the company—and the investor doesn’t have to feel like they’re paying you more directly.

  2. Focus on ideas that have near term revenue opportunities. Once you’re making money, all bets are off. The company has been de-risked significantly versus something that’s just a Powerpoint, and if you’re bringing in cash, you’re burning less. It’s easier to justify a higher salary when you’re making money.

  3. Don’t quit your job until you’ve raised. Sometimes, it’s not about having a high salary, but just having any salary that makes the difference for a founder. I can’t tell you how many times people quit their jobs first and then try to go fundraise, assuming you need to be full time on your company to raise. This is simply not true. You need to be full time on your company after the raise, that’s for sure, but there are plenty of teams that go nights and weekends to make some progress and get a term sheet based on that. I would never fault a team for needing to keep working until they get a paycheck post a raise.

  4. Set milestones. If you’re really confident in yourself, build in a step function of salary increases once you hit certain goals—a product launch, first revenue, etc. This way, you can address the motivation question and no one feels like the company is spending too much relative to the risk left on the table.

At the end of the day—you know the deal. The more money you spend on yourself, the less money you have for other things—and I would only back a founder that I thought understood this and could make wise choices given those constraints. I would only back a founder that was thoughtful about setting budget to begin with.


Thursday, February 20, 2020 - 5:38pm

As a founder, your most valuable asset is your time—and there is probably no group of founders who are more efficient about getting the most out of their time than moms. Moms also have a unique and personal insight into what’s important to other moms when they buy things for their kids. They’re looking for products that save time, provide good value, are good for their kids and have values they believe in.

Fatma Collins and Julie Rogers, former colleagues and both new moms, have just announced the launch of Ten Little—a children’s shoe company focused on fit and healthy foot development, as well as convenience. A child’s foot isn’t the same shape as adult feet—they’re a bit boxier—so their shoes need to be shaped differently, not just sized down versions of what their parents are wearing. They also need flexibility, to allow for kids to build balance and dexterity in their feet.

Parents can find their child’s size easily using Ten Little’s free Fit Finder by having their child stand on the insole prints or take a simple quiz on the site which prompts parents to share their child’s foot length or their current shoe brand and size. They also have a predictive data platform that tracks your child’s growth and sends you a reminder when it is time to size up.

In other words, no more dragging kids to a shoe store to find a fit.

This is also a brand that parents can feel good about associating with. Ten Little has partnered with Soles4Souls to put your child’s gently-worn shoes to good use. When you size up with Ten Little, they will automatically include a prepaid shipping label in your reorder so you can donate your child’s outgrown shoes for free.

What struck me most about Fatma during her pitch, which was made possible by an introduction from Anchor founder Michael Mignano, was her confidence in what she was doing. It wasn’t the confidence of a natural-born personality trait—it was the confidence that came from not only her experience as a potential customer, but a career in the e-commerce space.

Founders can be divided into three groups. First, there are smart, capable people—obviously, those are the ones you want to back over everyone you can’t fit into that group.

Within that, however, you can divide all the smart people into those that have done their homework and those who haven’t—and the right homework is where years of personal and professional experience has led to this very idea. The best founders aren’t months in the making—their company’s launch is the end of a years-long journey and the beginning of another. Everything they’ve been doing preps them in a unique way for what they’re about to do.

When they pitch, they’re not asking you whether you think something is a good idea—they’re there to tell you what they’re going to do. That’s what Fatma did. Her pitch mostly involved me listening and not a lot of debate on anything she said—because she knows her stuff.

I’m excited to have backed Fatma and Julie through Brooklyn Bridge Ventures—one of many pre-launch companies I’ve written a check for. They’re the 8th company I’ve backed that is founded by moms, and the 28th company I’ve backed with a female founder.

You can follow Ten Little on Instagram and Facebook.



Monday, February 17, 2020 - 11:38am

We’ve all heard the anecdotes—the famous founder who pitched 1000 investors before any of them said yes.

That kind of story drives founders to take a “VC’s don’t know anything” approach to their business and trudge on despite legitimate criticisms of the business, often costing themselves tens of thousands of dollars or more of personal savings.

So how do you know whether or not something is worth working on?

Most founders I know who are in this mode simply haven’t done enough homework and planning on the idea. They’re waiting and hoping something will “pop” without a real sense of what kind of execution would make that happen. They often harken back to apocryphal stories of how some conference drove some consumer app “out of the blue”, without acknowledging the network that was already using that app or how much more connected to influencers that founder was to begin with.

They think that if they just had enough money to market something, it would take off, yet whenever they pitch the app in front of a crowd of 100 people, the conversion and virality rate isn’t proven out at all.

Here’s a checklist that might be helpful in determining whether or not this is something worth working on.

Give yourself a point for every one of these you can say “yes” to:

1) Are you an expert in this space because of your own firsthand knowledge—enough to be asked to speak at a conference on the topic?

2) Are you the same kind of user of this service as the person who would be the buyer of its services, spending actual dollars?

3) Have you pitched a critical mass of investors of the right stage and sector? Is the feedback still inconsistent?

4) Have you given users a real shot at signing up and using the product—and a growing number of them use it and use it more often/consistently month over month?

5) Can you make whatever product fixes you need without raising capital to do so? (Because no one is going to fund a fix.)

6) Have you built yourself a financial model that includes both the profitability of an individual user, including the cost to acquire or sell them, as well as an overall growth number with a marketing budget over the longer term?

7) Does such a model get you to a long term size that makes sense for venture capital investors (north of $100mm in revenues)?

8) Have you made significant changes to the product or business model that improved key metrics over time?

9) Have you spoken directly to customers and gotten specific numbers on how much they would pay for this?

10) Is the service built in such a way that it still provides value for just a handful of users?

How many points mean you should still be working on this?

I don’t know the answer to that—but I know a lot of people have been spending a ton of time on things that I think at best would only net them 2-3 points. That seems way off, especially when they’ve quit their jobs or they’re spending lots of either their own money or friends and family money on this.

One of the reasons we build is for those founders that are spending real money on their startups—theirs or someone else’s. We put a price on it because we wanted to make sure we were sourcing founders right at the stage where improving the service, the pitch, and the chances of getting funded was a worthwhile investment. It’s not a crowdsourcing tool for feedback on ideas you came up with today—that you can do on Twitter.

It’s a way to get specific and consistent feedback from real investors at that point when you’re ok investing real resources into moving this forward. It’s less than the cost of a flight to an investor and less than the cost of a ticket to most conferences that are promising you connections to investors.

I get that budgets for a startup are tight—but if you’re about to fundraise or currently doing so and you don’t think spending less than $200 to find out what ten real investors are willing to share off the record about your pitch and plan, then I have to wonder what is worth spending money on.

We’re confident that the spend is going to be worthwhile—so if you get your report and you don’t think the feedback was useful, we will give you a full refund.

What do you have to lose?

The chances of the very first startup idea you have being the one is very low—and the best companies often go through several iterations. Learning and getting feedback is an integral part of the process—so if you’re not getting more than a handful of points on this checklist, maybe it’s time to start asking the question as to whether or not this is the idea that gives you the best chance of success.

Monday, February 3, 2020 - 1:37pm

I see this time and time again—a founder pitches a VC or an angel and they say to come back when there’s more traction. The founder then goes off and raises from friends and family or invests their own savings in the idea in an attempt to come back with a handful of customer or users.

In other words, the people with the least amount of money in this game wind up doubling down on what is probably an unfundable, problematic idea to begin with—because an investor said the only thing missing was traction.

Nearly all of these investors have funded someone they know on a Powerpoint or on a pre-revenue prototype. It’s not because they’re all part of some secret Illuminati group that you’re not in—it’s because they’re convinced that a repeat founder can execute, and they’re not convinced that you can. They might also be convinced of a repeat founder’s ability to identify what a big opportunity is and what isn’t.

At the end of the day, if they had 100% certainty that you could do what you say you were going to do and that the economic opportunity was there, they would jump at the chance to buy stock in your company today on the cheap.

They’ve done it before. Sure, they say they do it by exception, but every single time they fund someone, it’s by exception. Being exceptional is literally the requirement to get funded.

So whenever someone says “too early”, you should respond with the following:

“What is the thing that I have not done yet that you do not believe I can do?”

Unless you get that answer, you wasted the whole meeting. Make them tell you exactly what’s holding them back. People don’t pass because you don’t have customers—they pass because they don’t believe you can get customers, and there’s a reason why they think that.

Too many times, I wind up telling founders that it isn’t, in fact, too early, but that something just doesn’t provide enough value for customers or make enough money from each customer, and that the whole thing is problematic on its face. It’s a bit like telling someone their child is ugly, and maybe the founder won’t want to hear from me again, but at least they got real feedback.

It’s easier to handle if you’re getting that feedback consistently. That’s why we created We create a blind panel of 10 investors from venture funds who rate you anonymized pitch across multiple categories, providing you with a detailed report on how fundable and workable your idea is.

This way, you’ll know exactly why you’re being turned down and if it makes sense to double down and come back in a few months.

Monday, January 27, 2020 - 12:35pm

Every election cycle, you hear the same thing—Republicans are good for the economy and electing a liberal will tank it. This is especially the case this time around as we’re in the middle of the longest running expansion this country has ever seen—and no one wants the other shoe to drop. There’s a lot of fear that making the wrong choice will mess things up.

Not surprisingly, there’s very little evidence that either party has a particularly good or bad effect on the economy—and more evidence, in fact, that the President has very little impact on performance. That doesn’t stop people from taking credit or dishing out blame.

Rather than thing of our economy as a perpetual motion machine that will always just go up and down and that somehow a caretaker President knows exactly the right spot to kick it in order to get it to run correctly, we have to assess the unique challenges each time period presents.

Today, our economic competitiveness in the world is in serious jeopardy—and our ability to turn economic output into the health and wellbeing of our citizens has already slipped. This is of the utmost importance to measure, because, after all, what is the point of making money if you can’t enjoy it?

As I look upon the current state of the economy and the challenges that we face as an investor, it strikes me as being very clear what kind of an economy will work best if I’m seeking investment returns going forward—and that is a more progressive one.

What I mean by that is where new market entrants create healthy competition and push the boundaries of innovation. I mean a world where small business and big business can both thrive while sharing in their success with workers. I’m talking about an economy where the ills of an unjust society—housing, poverty, addiction, gun violence, healthcare, etc. don’t drag behind us like an anchor we forgot to address, costing everyone more and more human and monetary capital until we properly address it.

Here’s what I think a more progressive economy can do to ensure higher growth:

  1. Technology has created an unprecedented lack of competition—especially given our reliance on platforms—and it needs to be opened up in order to kickstart more growth. Forty years ago, access to consumers was much more open than it is today. Advertising mediums were more diverse and there weren’t a limited number of companies that customers had to touch before they could spend. Today, you do more online shopping than ever before—and 50% of that goes to Amazon. You access the internet through, at best, two choices of ISPs at home. When businesses want to reach an online customer most effectively, they basically have Facebook and Google to choose from to spend money on, creating a scenario where these platform companies have all the data necessary to pick and choose category winners. Amazon can use purchase data to create new Whole Foods brands and Amazon labels. Facebook and Google can get into financial services while boxing out advertisers of alternative products. While the right might tell you that government regulation gets in the way of competition, it seems pretty clear that it’s lack of government regulation that is the biggest impediment. Have we forgotten that the only reason Apple even exists today is because Microsoft feared the government’s anti-trust enforcement in operating systems. Microsoft literally floated its nearest competitor, which was on the verge of bankruptcy, in order to avoid additional government scrutiny. How would things have looked today had Apple actually gone under, which Microsoft would have otherwise had no issue with? We would have never gotten the iPhone and mobile technology would probably be at least five years behind where it is today, if not more. No one says you can’t make a lot of money—but when a small number of companies control access to key resources, sit on cash instead of continuing to innovate, and block competition, this isn’t a path to a dynamic economy.

  2. When you look at where the economic opportunities are, you have to look at where the problems are, and we face no greater existential threat to our economy than climate change. The creation of more sustainable goods, services, and transportation, cleaner energy, and environmental remediation technology represent a huge opportunity for the US to be a world leader and a growth opportunity. We’re not going to create lots of jobs building cars, but we might be able to do it building those windmill farms the President likes to make fun of. Only an administration that takes climate science seriously and thinks in terms of New Deal sized economic mobilization will be able to take advantage of this growth opportunity. Rolling back environmental regulations not only causes real economic costs in terms of healthcare and climate change related weather damage but it attempts to turn the clock back on an economy that just isn’t coming back and won’t be relevant in the future.

  3. It is pretty clear that we cannot sustain this level of military spending—especially in a world where the enemies we face are either not even nation-states at all, or they are nuclear powers where we cannot dare entangle ourselves with in conventional military warfare. The war in Iraq has cost this country trillions of dollars that could have otherwise been spent on infrastructure—the way China has. From a purely economic standpoint, investing in diplomacy has a much greater ROI than investment in war—and any general will tell you that. We need to rebuild our State Department so we can redeploy all that capital into education, healthcare and infrastructure, versus things meant to either explode or eventually rust away.

  4. To that end, we need to start taking into consideration wellness and other measures of the economy over and above the stock market as a measure of economic success. The opioid epidemic is literally costing the economy billions, if not trillions of dollars—so when you hear that stricter regulations and accountability stalls the economy, keep in mind what lack of regulations can do as well. This scourge has decimated communities and seriously damaged the labor pool with multi-generational consequences. When so few people even own stock, and so much of it is owned by even fewer, it just isn’t an accurate measure of how the average American or how a majority of Americans is doing. While our economy booms, our life expectancy is declining, lagging that of comparable countries. When two-thirds of the country can’t afford an emergency $500 expense and nowhere in this country can minimum wage cover the cost of a two bedroom house or apartment, it’s hard to say the economy is “working”. Sure, unemployment is low, but actual labor participation (the percent of working age people actually working) is declining. What is the point of making money if you can’t take care of people? Not only that, if more people’s basic needs are met, you’ll see more of a push towards entrepreneurship. No one is going to start a company if they’re tied down by healthcare costs and threatened by poverty—yet we know that all of our growth comes from the creation and success of small businesses. Whether they be local small businesses or venture backed startups, if we do a better job of providing for the basic necessities of healthcare, economic stability, and education, we’ll see more people set out to create new businesses—especially if the competitive landscape is fairer.

  5. Economic mobility is also key to growth. You’re not going to start something new or strive to do anything if you can’t see yourself moving up along with the success of the company you join. We’ve gotten away from sharing the wealth in favor of outsourcing contract labor. There’s no way you can say that our economy is better when a janitor is better off 35 years ago than they are today—but that’s exactly the case when you take into consideration the lack of upward mobility that employee has, as evidenced in this NY Times story. Outsized economic success doesn’t need to come at the expense of wages and benefits.

Looking at progressive policy as being singularly about higher taxation, lower profit, and therefore lower stock market returns isn’t just short-sighted, it’s too narrowly focused. When corporations profit at the expense of workers, those costs show up in other places around the economy. When lobbying buys off our politicians, we’re not actually operating in free market capitalism—we’re operating in a form of socialism in which the government props up the wealthy.

I’m an investor.

I’d like to make a lot of money—and I think I’m only going to be able to do that if we have a forward-thinking economy, an educated and healthy workforce that has enough stability to take entrepreneurial risks, and highly competitive ecosystems.

I don’t see the right providing pathways to any of these outcomes.

Wednesday, January 15, 2020 - 5:39pm

Raising a venture capital fund is hard enough. You’re going around to a bunch of people trying to convince them that you have what it takes to pick the big winners in a sea of aspirational companies that are destined for the scrap heap.

Now try doing that as a first time fund manager—without a long track record and lots of exits. Yet, that’s what has to happen if the profile of the check writers is going to be different than it is today. Barely 10% of the investing partners at VC firms are women and the number of investors of color is microscopic.

Since fundraising is often about who you know, and most people tend to be in networks that look like them, this exacerbates the problem of diversity in who winds up getting venture dollars.

One way to change this landscape, instead of waiting for VC jobs to open up is to go out on your own and start a fund to invest in the opportunities you see in your own community. Unfortunately, the way the Limited Partner landscape is setup and the nature of SEC rules, emerging managers are fundraising with their hands tied behind their back.

Most bigger institutions won’t invest in first time funds—and even those that do tend to need to write a minimum size check to make it worthwhile. They also don’t want to be more than 20% of a fund. The reality of fundraising for a new, smaller fund is that you’re mostly going to wealthy individuals to raise.

Here’s where it gets tricky.

You have to be an Accredited Investor to put your money into a VC fund, but the way the system works, there are many accredited investors who wouldn’t be able to meet the minimum investor requirements the system forces VCs into.

The rule on a fund is that unless everyone is a Qualified Purchaser, meaning they all have $5mm in assets, you’re stuck with two different types of limits on how many investors you can have. If your fund is no more than $10 million, then you can have up to 250 (or, 249), but if you get above that, it’s 99.

So, if you want to have a certain sized fund and you’re capped on the number of LPs, simple division gets you at a minimum number each person has to invest to hit your goal.

This is the 99 Investor Limit Problem that Brad Feld describes here.

I guess the idea has always been that for something so risky as VC, you only want “sophisticated investors” involved—with “already rich” being a proxy for sophisticated. God forbid the average person gets a cut of the pre-IPO growth of all of these companies that hit the public market like a falling knife.

The rich people got to invest in Uber for a 5,000x return, but the rest of the public had to wait to get a…

* checks current share price *

…negative twenty-five percent return after it went public.

Point being, you’re off pitching to rich people—and not just rich people—super rich people way over and above the minimum accredited investor numbers.

Well, what do we know about rich people. First off, they tend to be overwhelmingly white and male. We have heard about pay gaps in this country—about the cents on the dollar various groups are making compared to white men, but the wealth gaps are even worse. For every $100 of wealth in a white family, the average black family holds a little more than $5 worth of wealth—and wealth is a better predictor of who can invest in venture capital, a long term asset class in which people are only putting part of their money into because if its high risk.

This is all context around what the investor number caps mean for the kind of money you need to ask people for in order to build a decent venture capital fund.

Let’s say you want to go raise a small seed fund. You’re not even looking to go big. You want to write $100k checks and be done with it. You can’t really lead rounds and you can’t support them over time. Here’s what it looks like in terms of people able to raise from just “normal” wealthy people, assuming they’re not all super-wealthy (Qualified Purchasers).

Screen Shot 2020-01-15 at 10.21.34 AM.png

Ok, so assuming with some recycling, maybe you get to 95% invested across 30 deals, if you maxed out on the number of LPs allowed, each person would only have to do about $4k per year for three years. That’s not too bad and I think someone who is well networked actually has a shot at this.

But, look at how the numbers change as you want to write more meaningful checks.

Screen Shot 2020-01-15 at 10.24.36 AM.png

If you want to lead seed rounds—backing founders from diverse and underrepresented communities, for example—you’re going to need bigger checks, especially if capital willing to co-invest in these communities is sparse.

Look at what happens when you cross over into that $500k initial check size—your fund busts through the $10mm limit for an “angel fund” and now your base of allowable investors shrinks to 99. That means that the minimum investor who fulfills their three year investment period commitment goes from writing a $4k check a year to over $53k, even though the fund is barely 5x the size.

Investing over fifty grand per year in a VC fund is some serious dough. When you separate the universe of potential VCs between those who can source 99 $50k check writers per year and everyone else, the stats on who is connected to wealth within their network is going to dictate that group is a less diverse pool.

Now, look at the numbers if you want to have a more substantive strategy that continues to support these companies over time with follow-on capital.

Screen Shot 2020-01-15 at 10.31.37 AM.png

At 50% reserved, you literally cannot create a VC fund that is in a position to lead using these limits unless you know people who can write checks of $80k per year. Even writing checks of $250k is going to be a struggle, because going from $100k to $250k means you need about 7x the average annual LP check.

Now imagine if the limit was 500 investors. Thanks to fund administration platforms like Carta, the technology is there to easily manage these pools of investors, so that’s not a problem.

You would have this huge network of potential fund supporters and here’s what the stats would look like:

Screen Shot 2020-01-15 at 10.36.11 AM.png

This makes a huge difference. Now, you could be out writing half million dollar checks and reserving half your fund for follow-ons, and each underlying investor is only responsible to fund $16,000 per year. Sure, not everyone has that, but way more people can do that than $80k.

Plus, at this level, you could get those same investors backing multiple funds at a time, which is better for competition among funds, and also broadens the base of who gets experience in VC. They’d also be more likely to keep backing these funds for their Fund II, III, etc., and not stop putting money to work while waiting for those early payouts from the first fund.

It’s also better for the limited partner. No longer do they have to risk huge chunks of capital to get exposure to this risky asset class. More LPs could get involved with less money each—and those investors will also tend to be more diverse.

The vast majority of LPs I’ve had to turn down because they couldn’t meet my minimum check size of $250k were women and people of color. I’ve even stretched to be inclusive of those groups and lowered the minimum for some, and it’s still incredibly difficult. For every “stretch” LP I take below the minimum, I have to find a bigger one to balance them out in the average.

People worry about over-investment in the asset class, but what we’re talking about here is the tiniest part of the asset class. You could create 40 funds of $25 million each and it wouldn’t equate to a quarter of the new money that WeWork got after its disastrous implosion.

What you would get is a whole bunch of new startups blooming, able to hire because they have funding and more chances for larger VCs down the road to have backable companies to take to the next level. Plus, you’d probably get a lot of diversity in the types of companies being backed, the approaches of the founders and the geographies of where they are starting.

Lowering the bar on how much an LP has to lockup in a fund makes raising capital for new and emerging managers easier, provides more accredited investors access to the asset class, and undoubtedly would diversify the pool of people running funds.

Thursday, December 5, 2019 - 5:37pm

There’s one thing that no one can ever take away from Adam Neumann—he was world class at fundraising.

His ability to tell a story and gain investor confidence was unmatched relative to the underlying progress of the company. He exuded confidence told people he was going to change the world.

It’s not actually surprising that investors bought into it, considering that for a long time, VCs have focused on one particular archtype of leader as being more worthy of venture investment than others—the bold, confident visionary who will talk big in the pitch meeting.

As an investor whose portfolio is run by diverse founding teams more than 50% of the time, I’ve noticed a difference in how people relate to talking about the future across various groups.

There are some founders who see predictions about the future as a kind of promise—and so they hesitate and get uncomfortable around the idea of insisting that X, Y, or Z will happen. They tend to pause or give concessions around direct questions.

“So, what will your margins on these new locations be?”

“Well, it depends on the location…and obviously, they need some time to get up to peak efficiency…but we think we can get somewhere between 30-35%”.

That sounds like a less confident answer than just “35%”.

But it isn’t.

It’s a more complete answer in the mind of an operationally focused founder.

If you flip the question around and said, “Do you think you can get 35% margins here?” that same founder will give the most unequivocal, most confident “Yes!” you ever heard. They just don’t like making solitary, definitive statements without making sure you know all the variables and caveats—so you can be as informed as possible and not surprised at all when things don’t go exactly according to plan as typically happens in a startup.

Those founders tend to be terrific to work with on the operational side. As an investor, you tend to fill more informed about the complete picture of the company’s performance—and not like you’re having smoke blown at you.

They don’t fare as well in fundraising, however. Investors might say they lack confidence or it feels like they aren’t really “on top of” their business, when in fact, they know their business extremely well.

In my experience, those founders are disproportionally from underrepresented groups. My theory is that in a world where they experience a lot more scrutiny than the average straight, white male founder, they’re more conscious of what it means to take on investor capital and the expectations around performance that it brings.

I think our view of successful leadership style needs to change just as much as these founders need to be more aware of the fact that we as investors are in this to take the risks, and that no VC is going to go homeless if a deal doesn’t work out.

You don’t need to tell us all the caveats around your prediction of margins, but we shouldn’t fault you if you do. Maybe it’s time we changed our perspective of what a strong leader looks like—that it’s someone who is transparent around the risks and is more conservative about predictions while still striving just as hard to crush expectations.

“Maybe it’s time we changed our perspective of what a strong leader looks like—that it’s someone who is transparent around the risks and is more conservative about predictions while still striving just as hard to crush expectations.” -

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Does it make sense to write a bigger check to someone who talks a bigger game without being conscious of the execution details they need to get right to back it up—or someone who sweats the details, too?

Obviously, it doesn’t need to be either extreme, but I see too many otherwise terrific operators getting dinged in a fundraising meeting because they didn’t act like the ringmaster at a circus. We should be more ok with people who act in a fundraising meeting like they do at a board meeting—collaborative, flexible, opportunistic, and willing to measure twice before cutting once.

Here’s one way that these types of founders can win more investors over without trying to be someone they’re not: Own it.

Enter a meeting and set the tone by saying something like:

“Just so you understand where we’re coming from and to set a context for our conversation. We’re operators and we’re meticulous about getting all the details right that form a strong foundation for this company. We built a culture based around transparency and thoroughness--so when we talked to our team about what we’re going to accomplish, we don’t blow smoke. So, if you feel like you don’t hear a bold line like “We’re going to put a TV in every household one day” that’s not because we don’t think that’s going to happen—that’s because we know there’s no point to doing that unless the TVs actually work. Don’t mistake that for any lack of enthusiasm about the business or the size of the opportunity. This is a huge market and there’s no reason why this can’t be a public company one day—but we’re here to make sure we’re all on the same page about the plan to get there and to show you that we’re eyes open on the risks and that we can handle them.”

If Adam Neumann had run WeWork like this, he might still be running WeWork.

If you want to know whether or not your pitch resonates with VCs, check out to get a report on how an anonymous panel of VCs feel about your company. Use the code FOUNDER50 for 50% off and sign up and submit ASAP before the next cohort of reviews fills up.

Wednesday, December 4, 2019 - 11:37am

A lot is made of the best practices around raising capital—but I think a lot of the advice is a bit too clever. First off, most of it is parroted by people who never raised any money.

No one ever says, “My idea wasn’t good enough and that’s why we didn’t raise.” They’ll come up with a lot of reasons why raises didn’t happen, like “The round fell apart because it was too close to the holidays.”

“No one ever says, “My idea wasn’t good enough and that’s why we didn’t raise.” They’ll come up with a lot of reasons why raises didn’t happen…” Click to Tweet this quote

VCs want to make money and there’s more money out there than there are good ideas—so I just don’t buy into the idea that there are a bunch of good companies out there whose fundraising purely depends on getting into a VC’s inbox on the right day of the calendar. When a company is beating its plans and a team is super compelling, a VC will go out of their way to fund something no matter what time of year it is.

That being said, VC bandwidth is limited—so if there are times when more people are pitching versus less, or when they are working more or less, that might have an affect. However, if you follow the conventional wisdom, everyone should pitch in January and no one should ever pitch two weeks into December.

But, if you were the one maverick who did pitch two weeks into December, and the VC isn’t off for vacation yet, than wouldn’t your chances be greater?

I think founders should be more concerned with “How can I get on someone’s calendar” than when the deal will actually close. There’s something to be said for trying to get onto the calendar during times when it isn’t likely that anyone else is—like those August and December time periods. A few years ago, I went to SF to connect up with other VCs and went 12 for 12 in getting VC meetings the week before Christmas. No one takes off that week and, not surprisingly, no one pitches.

You should be pitching when you have the best story—when the money and resources you have as taken you as far as you can go while still leaving yourself enough runway to raise. But how do you know when that is?

At Brooklyn Bridge Ventures, we created a kind of focus group for venture, populated with real VCs. It’s called and it’s a double blind system that looks a bit like a YC application. Ten VCs look at it and give their feedback anonymously, with the results being summarized in a report that looks like this.

If you want to be one of the first to check it out, use the code FOUNDER50 for 50% off the feedback report. This way, no matter when you pitch, you know you’ll be putting your best foot forward.

Tuesday, December 3, 2019 - 11:42am

If there’s any one thing I’ve focused on in my VC career, it’s trying to give real, actionable feedback to founders. I’ve made a bet that if a founder pitches me, whether or not I fund them, if I make the process worthwhile by telling them exactly why I couldn’t get there, they’re likely to recommend that other founders do the same.

The risk is that if I give a definitive “no”, then if they pivot, or figure out something else, or if they get more traction than I expect because I was flat out wrong, then I’ve closed the door on my opportunity to invest.

I’d rather do that and take that risk then give them wishy washy, meaningless feedback that blends in with all the other investors that do the same.

There are other reasons why the process of fundraising doesn’t provide good feedback, leaving founders frustrated and uncertain as to why they’re not getting more investor traction.


As investors, we offer money as our product—and the demand for it is high. Our inboxes are full and it takes a lot of time to try to get back to everyone.

Part of what makes the process take longer is the format—you write a long story in pitch form and we’re supposed to write one back. It would be so much easier if investors could quickly get to what matters, and give them quick directional responses—yes to this market, no to this team, yes to this way of making money.


A no is a no, and since most VCs try to sugar coat things a bit, everyone walks away feeling like they just missed getting a meeting or getting funded. You really have no objective way to determine how close you came.

Not only that, but whatever commentary or criticism we do give might not be commensurate with how good you are. Maybe I mentioned market size, but I could be grasping at straws for a near miss and that’s not actually a really big issue.


I recently got pitched something that I wanted to say, “You’re a terrible person for thinking this is a good idea” but I didn’t want to start a fight with the founder nor have that founder go around badmouthing me in the community because of the feedback. However, that’s what I really think.

If I could have said it anonymously, I probably would have—and honestly, I think that’s what this founder needed to hear.

A VC’s interest in keeping relationships open sometimes flies counter to their desire to give honest feedback.


It’s really hard to keep track of every investor’s response and lay them out side by side to figure out if you’re getting strong signals on particular aspects of the pitch. After dozens VC pitches, most founders don’t get feedback given to them in such a way that makes it easy to create a narrative as to what’s wrong.

A Solution?

About a year ago, Lauren Magnuson and I started looking at how to go about getting founders real feedback. We talked to a bunch of investors about what was important and to a bunch of founders as to what they were trying to get across.

We did this because we believe that if founders are going to invest their personal resources into a project—time, money, reputation—and take that big career risk, it should be easier for every founder to get honest and specific feedback from real venture capital investors.

We created—a double blind system where a panel of investors review anonymized submissions along a structured format designed to give you feedback specific to crucial aspects of your business--product, market, economics, team, and raise. This way, you can find out what’s actually resonating with potential investors and also what needs work. Not only that, but investors can request to be connected with you directly if they like your anonymized submission.

If you’d like to be part of our first Beta cohort, you can use the code FOUNDER50 for a 50% discount.

Is this pay to pitch?

No. We don’t believe in charging for direct access to VC’s, and that’s not what we offer. What we have heard from founders time and again is that direct meetings with investors don’t always garner honest and consistent reactions. Anyone can pitch whoever they want, but not everyone gets the detailed, specific feedback they're looking for.

Why isn’t this free?

We would love to be able to offer this service at no cost to the community. As a small fund, we’re not able to sustain the costs in time and resources it takes to build and run the platform. We offer discounts to underserved communities, and we will be donating a portion of our proceeds to CodeNation—a nonprofit that equips under-resourced high school students with the skills and experiences that create access to careers in technology.

Who is this for?

This product is aimed at founders who want to set themselves up for a successful fundraise by getting honest feedback from real investors. You get a detailed review on several aspects of your business, so this isn’t for an idea you just had in the shower. And since our investor panels have a limited time capacity, we’ve designed this for companies who are at the stage of investing in the improvement of their business. Our aim is to make your raise more successful in orders of magnitude more than what you invested.

Monday, November 4, 2019 - 12:34pm

If you’re an great engineering manager in a startup city, changing jobs into a similar role is pretty easy. For most people, though, things are a little more difficult. Not everyone has the most sought after position and many work in a job where figuring out what skill set you have to offer isn’t so cut and dry. I would say most of the market isn’t working in a position that is so linear either—so you may be doing something a little different each time, making the searching part of the job more difficult than just finding openings. First, you have to figure out what you’re looking for, which isn’t easy.

Here are some tips on how to go about it:

First, be patient and respect the process. This isn’t like looking for your keys, where you poke around a handful of obvious places and when you find exactly what you thought you were looking for, you’re on your way. This is more like being asked to find “something special” in a stranger’s apartment… in a foreign country. There are so many other pieces of information you’ll need to uncover first before you’re pretty sure you know what you’re looking for, let alone before you actually find it. Try to reset your expectations about how long it should take and what the process looks like. Don’t get too down over yourself over not knowing how it ends before the process starts. You’ll be on a journey. Enjoy it for all that you’ll learn about what’s out there and what you’ll learn about yourself.

Don’t focus on the job—that’s the end of the process. Focus on the next step. If you decided you wanted to get in shape to run a marathon, you wouldn’t start fretting on day one that you can’t run a marathon. You wouldn’t stress out about running a marathon as if you’re running tomorrow. Step one would be about creating a plan, maybe deciding if you need a coach, and talking to a lot of other people how they went from not being a runner at all to running a marathon to feel out the different approaches.

Here’s what your process should look like:

  1. Gather info by activating and broadening my network.

  2. Try to be helpful to people I like working on problems I find interesting.

  3. Make sure my network knows I’m working on these things and show my approach.

Notice none of those things involves searching job sites or applying to anything. Searching a job site is akin to searching on Amazon. You shop Amazon when you know exactly what you want. When you’re not sure, you discover. You browse Pinterest or Instagram, and you don’t stress about not purchasing something at the end of each session. Changing your job is more about discovery for most people than search.

Set goals for networking. Setting and hitting goals is satisfying—which is why you need to set goals in your search that are more than just “Get a new job.” You need week to week goals that are achievable, because it’s important to feel like you’re moving forward in what can otherwise feel like a very stressful time.

How about “Get introductions to three people a week that have interesting career paths in areas I could be interested in” or “work on an panel event where I get to ask someone I admire questions but also position myself as a thought leader in my space.” Those are things you can do this week that have nothing to do with knowing exactly the job you want or how to get it.

Figure out a schtick. The best networkers have a little bit of a routine. They often repeat the same phrases about how they describe what they do, what they’re looking for, and some help they can offer someone else. It’s just easier and less stressful to have a tested set of things you can pull from around how to move a conversation to ways that you can be helpful or how to describe what you’ve done.

Here’s what you should write out and practice for the next connection you make:

  1. What’s a description of what you’ve done that lets someone know what you’re good at. So, instead of, “I was VP of Creative at a Toy Startup” tell them “I build brands—everything from product design to marketing copy—and I’ve done it most recently for a company in the Toy Space, but I can do that for any kind of design oriented company.”

  2. What are the next steps? Do you want to hand out a card. Do you have a newsletter someone can follow? Do you just want to e-mail them a blurb about a working lunch that you offer to companies as an advisory exercise?

  3. Ask who they know who either a) needs help or b) who their go to person would be that most closely resembles something you might want to do.

Find a way to get public in a way you’re comfortable with. Unless you just want to play the job post and resume game, your goal should be to create some inbound—and to do that, you need to be top of mind for people. Maybe it’s a podcast, a newsletter, an event series, or just a monthly small group networking lunch—but whatever it is, you need something others can point to and say “Hey, you should check out this smart person doing this interesting thing.” It’s the equivalent of having sharable landing pages on a website and that’s going to help opportunities come your way.

Once you get ideas, people and your reputation flowing, the rest of the process is much more blocking and tackling, finding openings, doing the interviewing. That also requires a lot of patience—and it can often be made easier for both sides through consulting. Allowing both sides to get to know each other lowers the risk—and the key there is having an offer that results in a deliverable they really want. If you’re applying for VP of Marketing plans, offer to write up a strategy, timeline, and budget first—because it’s something they need anyway and it will show off what you’re capable of before they need to pull the trigger on a long term deal.

And again, be patient!!



Wednesday, September 18, 2019 - 5:34pm

I believe that the next generation of top companies are far more likely to be founded by people not on VC radars today. Today's top founders will undoubtedly start something new in the future, but they won't make up the majority of innovators going forward--just as prior generations of venture backed founders don't make up a majority of those who are succeeding today.

That believe has not only translated into the most diverse portfolio run by an investor who looks like me, with over 50% of the teams including diverse founders, but also into top quartile returns in our last fund.

But diversity isn’t any kind of criteria for us—it’s a function of trying to create value for the whole ecosystem--not just those you back. Opening up our circle to create and scale genuine engagement for people outside of typical venture networks is how we do business—and we’re getting exceptional deal flow because of that.

I believe that the next generation of top companies are far more likely to be founded by people not on VC radars today. Click to Tweet this Quote

We backed four of the female founders in the Inc Female Founders 100 list—another five we passed on and two had rounds oversubscribed before we got a chance to invest. (Hey! I didn’t say venture investing was easy—but at least we got a look.)

Just yesterday, I got a note from a female founder of color:

“Earlier this year you invited me to one of your off sites and that made a huge difference for me as a founder raising capital for my first company… I'm just looping back with the individuals who were helpful and who said "yes" to me during a pretty grueling process. You passed on investing in my company but you still made an investment in my leadership and I'm deeply appreciative.”

Last week, we ran Fall Fundraising Days, which featured 11 NYC events on raising capital that 800+ individuals attended across the week. Most were open to the public, but we didn't stop there--we intentionally sought out recommendations for underrepresented attendees and didn't stop making those asks as the events filled up with greater balance than your usual tech event.

This story from Cherae Robinson was just one other example of how our events helped someone we didn’t back (we have a portfolio conflict) reach their potential.

Venture is all about access—getting the best deals. That access cuts both ways—because at our stage, we need to make sure the best deals can get to us.

That means, to start out, no need for warm intros, since everyone’s network looks too much like themselves—but that’s just table stakes.

I generally accept any invite to speak or answer questions in front of a public group that I get.

We run a series of best practice workshops where we put top VCs in front of audiences of new junior professionals at funds and accredited investors looking to start angel investing—and we intentionally seek out underrepresented people to join. (Contact me here to find out more about this.)

We host neighborhood dinners across different parts of NYC—from Park Slope to Harlem, and the West Village to Bushwick, and beyond, to connect startup and tech professionals to their neighbors.

For the last decade, I’ve been sharing open events, opportunities and info in my weekly tech newsletter.

So come participate in the community we’re creating around Brooklyn Bridge Ventures.

Friday, September 6, 2019 - 2:33pm

I got asked by a reporter yesterday what I thought about WeWork’s IPO situation and I’ll summarize what I said here:

First off, let’s pull back for a moment and acknowledge that WeWork has built a huge company that generates a ton of value for its members. Real estate was previously a huge headache for small businesses before WeWork made co-working mainstream.

I don’t know where its valuation will wind up, but I believe that there is a going concern there that is worth billions of dollars. How many billions is for the public market to decide but there’s no doubt in my mind that the underlying value of renting out big chunks of space and using tech enabled, streamlined processes to sublet it out in smaller chunks works. After all, that’s what hotels are, right?

Plus, if you were an angel or Series A investor in WeWork, no matter how this plays out, you either would have cashed out by now for a huge return or still done enormously well in the IPO. If any one of my seed investments ever needs to debate whether its worth $40 billion or $20 billion, I’ll take on that headache any day of the week.

What it does bring to mind for me is the perception of risk.

A lot of people think early stage and seed is really risky, but risk is a function of return—and returns are a function of price. I would argue that a portfolio of making bets that late stage, but still unprofitable companies like WeWork are going to be worth X billion dollars and buying in at a huge valuation is way riskier than buying a basket of promising early stage companies at single digit millions of dollars in valuation.

At least the small companies have lots more opportunities to get gobbled up for some amount of value even if they don’t ultimately work out as well as you would have hoped.

Plus, the overall dollars invested tend to be smaller. A small fund like Brooklyn Bridge Ventures might have minimum investment sizes of a quarter to a half million dollars—whereas a late stage megafund probably expects its LPs to put multiple millions to work.

These late stage funds are often the ones that get crunched in market downturns—because they find themselves over their skis quickly on valuation—whereas early stage funds have longer time horizons anyway. Seed investments made now are expected to exit sometime after this next recession will have likely played itself out.

I also think seed and early stage managers are more aligned with their LPs. A $10mm, $25mm, or even $50mm fund isn’t generating enough management fees for anyone to get rich off of just taking your money—so they’re out looking for big outcomes.

A multi-billion dollar megafund that is investing in the late stages of companies like WeWork makes a lot of fees and can afford to treat late stage rounds like options. They’re going in at high valuations using preferred securities—meaning they’re the first money out in a downside exit. Sometimes they have various ratchets and other bells and whistles that protect their downside further, like when Square IPO’d.

They also have lower upside, since they’re going in so high to begin with—so the percentage of money they’re ever going to make on fees is higher versus a smaller, earlier fund that really needs upside to cash in.

The other area to consider is the timeline. WeWork is under 5% of all of the commercial space in NYC—its home market. If all real estate goes the way of server infrastructure, with no one ever signing a commercial lease except for larger campuses like Google and Apple, then WeWork hasn’t even scratched the surface of its potential. Today, Amazon’s AWS product is probably worth hundreds of billions of dollars because who buys their own server anymore—but when they first started, people thought of it as a money losing distraction. If WeWork, like Amazon, is betting on a much longer term view of the market, the price could be justified.

One thing is for sure—there does seem to be a lot of hair on this deal. The IP transfer from the founder, his family’s underlying interest in some of the real estate—it might end up being all square, but it just gives people pause.

I’m convinced WeWork is part of a sea change in how business think about real estate, and from great disruption comes great economic opportunity. Companies like Lina (a BBV portfolio company), which creates joint spaces for medical practices, will pick apart other segments of the market created by this disruption and lots of winners will be created.

How big these winners will be is not a game I’m in. When you operate out of a $15-20mm fund, a winner is pretty much a winner at almost any size.

Monday, July 15, 2019 - 11:30am

“I didn’t want to bother you.”

“I didn’t want to impose.”

“I didn’t want to show up with my hand out.”

“I feel like if you were interested, you would have said something already.”

“I wasn’t sure if it was ok to ask.”

“I haven’t spoken to that person in a while—it might be too random now.”

Do any of these lines sound familiar? Too often, I meet founders that need something, and feel awkward about asking for it for a variety of reasons. Disproportionately, the ones who hesitate to make the ask are women or people of color—at least in my experience.

Speaking from a position where I often get asked a lot, what I don’t think people realize is what the other half of the exchange is in an ask. If a startup pitches me, for example, they’re not asking—they’re selling their equity. That’s a fair tradeoff (at least, if they don’t think it is, they probably shouldn’t have quit their job to start this company.) If no one ever pitches me, then I’ll have no companies to invest.

And if I know the person, I’d so much rather get a pitch from them than someone I have to get to know from scratch (although I’m happy to take cold pitches anytime, too!).

Pitches, while asks for the founder, are potential opportunities for me. Even if I don’t find the company, it’s an opportunity for me to learn about a new space, or just to be helpful enough where you might recommend a founder come and pitch me later on—and maybe that founder is the next big thing.

Most people like feeling helpful—it makes them feel less alone and more useful to others. An ask is really an offer of purpose to someone else.

“Here’s something you can do to help me,” can be a welcome interpretation of an ask if someone is feeling low on self-worth.

You should never be scared to ask for something you need—because the worst thing that can happen is that someone says no. Anyone who dings you just for making an ask, saying perhaps that you’re too needy, probably was never really going to help you with much of anything anyway, and probably doesn’t add much value to your life.

No person is an island—and getting ahead means getting help from others. An ask is a very simple way to direct those who are interested how they can help—because you probably have a lot of people in your life who would help you, but aren’t sure what you need.

I wouldn’t have gotten my first job in venture capital had I not asked to extend my internship part-time past its original deadline. I wouldn’t have gotten that internship if I hadn’t asked if there were other opportunities after interviewing for a few that I didn’t love.

And if you’re ever concerned about making too many asks, you can ask just one more—ask how you can help someone that you’ve asked for help from.

Monday, July 8, 2019 - 11:30am

Running a startup consumes a ton of time. Just the immediate priorities seem to take up more than one person’s potential working hours—so it’s no surprise that when it comes to something like social media, many founders have trouble making it a priority.

The consequences of failing to position a founder’s profile aren’t always obvious—and it’s usually all about missed opportunities. Some founders get more press, get speaking opportunities or have an easier time fundraising thanks to leads that started with social media. Does just randomly posting on Twitter mean an automatic Series A?

No, of course not.

But if you have to start your VC list from scratch when you’re thinking of who will fund you next and all of your PR outreach is just a bunch fo cold e-mails, you’re starting from behind the eight ball in a way you wouldn’t have had to had you just participated in the public square that is social media in small amounts daily.

Here’s a primer on manageable things a founder can do to create and take advantage of social media driven opportunities for the benefit of their company.

The Base Layer

The very basic level of participation on social media isn’t posting—it’s listening. There is a public conversation going on around people who need to know about what you’re up to and that you ultimately benefit from having a professional connection to. Being unwilling to listen to that is foolish, because it’s good information—and it’s networking 101. Any relationship you build should start with listening first, and social media, despite what you might think, is no different.

Where you can outsource some of this to interns, researchers, a PR firm, your team, etc. is figuring out who your top 250-500 list is. Take the time to understand that if there was a conference full of people that would be highly relevant to what you were doing, who would they be? It’s some combination of industry leaders, other founders, academics, media, big company folks, etc., but in the end you should know exactly who your best few hundred (or more) potential networking leads are, and follow them. Conferences are actually a good place to start to find these lists of folks, as someone has done the job of curating a list for you. You can also look at the list of who other people in similar positions follow. For example, if you were the founder of a self-driving car startup, checking out who the founders of the other dozen self driving car startups follow might be a good place to start.

Generally speaking, I think Twitter and Instagram are good places to start. Twitter feels like a given, whereas Instagram is a bit more personal, but as long as people don’t have private accounts, they’re fair game. It’s often a good way to figure out if there are hobbies or interests you share in common with someone.

Now that you’ve got your follow lists, I would think about perhaps 10-15 minutes per day as a pretty good investment of time checking out what’s going on around you. Share or retweet what you find interesting, ask questions, comment, etc., but do it authentically. Don’t comment just for the sake of commenting—comment only when you have something to say.

If you took the time to pick out 500 industry people who are ultimately the right people for you to connect to given what you’re doing, and you follow them for 10 minutes a day for the next 30 days, but still have nothing worthwhile to say in response or can’t find anything worth sharing—I think maybe you need to reconsider whether you’re really passionate enough about this industry to be in it for the next eight years.

The Angle

Think about an angle—some unique insight—that you bring to bear into these conversations as you start to post. For example, if you were the founder of some new home workout device, posting about fitness isn’t unique enough. Posting about how hard it is to fit fitness into your routine as a parent of three kids—that’s something unique to you that you could imagine being a magazine article.

It doesn’t always have to be about you and your company either. Maybe there are some people you follow who have created great little routines to squeeze into your day doing everyday things—like doing calf raises stepping up and down from your tippy toes as you wait for elevators. Sharing that type of thing helps build your narrative but it also curries social capital with others—because sharing is a currency you can build up.

Long Form

Medium, LinkedIn and various contributor networks like Forbes are great places to get extended stories out. What is it that you would share if you had the opportunity to give a talk at a conference—this is where that kind of message goes. The best way to write long form articles is to keep your reader in mind—what is the interesting thing you’re giving them that is going to be conversation-worthy for them later. Can you imagine them talking about it later at a networking event? Probably not if you’re writing a post on “An Overview of the Banking Industry” but probably yes if the article is “Is the Fintech Startup You Just Signed Up for Worse than Your Bank?” This would be a good way to talk about ethical issues around money and data, and how your company has made a promise never to sell its user data.


A lot of opportunities for founders to be on panels and on TV come from posting video clips. Just because someone writes well doesn’t mean they’re well spoken and perform well on camera—so showing off your speaking skills on video can go a long way to creating more interview opportunities for you.

If you don’t have the money or time to setup a video studio (Who does?) you might check out a company I invested in called Openreel. Openreel allows you to capture HD quality video from your phone, tablet or laptop with all of the controls available to someone using a professional setup with a director. You can even have someone else do the capturing and controls remotely and it comes with a teleprompter feature as well. It’s a fraction of the cost of rolling in a video crew everything you want to shoot something, and an order of magnitude higher quality and more professional just doing selfie videos on your phone.

With this kind of solution, posting a video once a week isn’t a big ask—especially if you just spend an hour banging out three or four at a time. Similar to the longer form posts, try to think of sharing something meaningful that you want people seeing when they search for you—like why you started your company, what’s important to you about this business, or something specific about your leadership style.

Obviously, when you’ve got multiple types of posts—long form on Medium, videos, etc. you’ll cross post across your various channels. This is also a good spot to outsource. Put someone else in charge of making sure your LinkedIn connections know you wrote a Medium post and vice versa.

Engage Others

One way you can build up your following is by engaging others. Write posts where you pose interesting questions to others—giving those people a reason to share things that you compose, along with your profile. If you’re eventually going to be fundraising for a wellness startup, it might be worthwhile to ask 50 investors about their own wellness routines—or, if you’re looking to stir the pot a little, measure the wellness routines of the founders that those 50 investors backed and point out the likely differences.

Interviews other others are a great way to punch above your weight as you build your profile. Most people are willing to have content composed about them for SEO purposes or even to have something to share to their own audience if you’re willing to do the editing.


Not everyone is comfortable posting every last intimate detail of their lives on social media. The good thing is, no one is asking you to do that. However, it’s not an unreasonable ask that there’s some human semblance of you on the internet that a potential hire or funder can find if you’re asking them to commit several years of effort to helping you. When you post about what’s important to you outside of your professional life you build not only a multi-dimensional image of yourself that might give others a better picture of whether they want to work with you, but it also increases the potential ways to connect with key stakeholders. Maybe there’s a VC that also plays the sport you do, likes puzzles, or who can relate to stepping on their kid’s Legos in the middle of the night—and when you’re a founder, you could use any inroad you can into a conversation.

Bonus Points

Here are three next level media strategies that I think have a significantly high ROI and might actually take less resources than you think:


You can use a tool like Zencastr or even a video capture tool like Openreel to create interviews for podcasts very easily—and a basic suite of Apple software like Garageband can get you pretty far in terms of basic editing. A single interesting podcast interview can hook an investor’s attention and running a show can excellent excuse for connecting with high level stakeholders. Running a logistics startup? Interview the GM of North America for UPS. Got a new parenting app? Interview an influential or celebrity mom or dad.

When you’re starting out, much of the value of doing things like podcasts isn’t necessarily in the building of a big following—although that can happen over time. It’s all about having a reason to connect with someone that isn’t so transactional and that gives them some value, too. Instead of grabbing coffee to pick someone’s brain, which is particularly one-sided for them, invite them to an interesting podcast conversation they can share with their own audience. Instead of cold-pitching the media, bring them onto your podcast to share their expertise.


Getting a professionally done survey from a real firm costs about the same as one month’s worth of retainer from a PR firm—but is bound to get you way more in terms of press hits. There’s nothing more sharable on social media than data—so let the numbers make your case for why you’re starting a company in this space. Moreover, why not let customer surveys create leads for you? Google “indoor farming data” and you’ll find Artemis Ag’s (formally Agrilyst) State of Indoor Farming Survey, which added a windfall of leads to their sales pipeline. You can work with a media outlet or professional society to get a whole bunch of potential folks in your target market answering questions that they all want to know the collective answers to.

One Day Conferences

You can book a space and feed everyone in a nice space for less cost and effort than you think—and create a lot of content and connection in the process. In fact, if you just need to break even, you can often get sponsors to cover much if not all of the cost of it. It’s also a good excuse to invite interested investors and get into a conversation with them. You could literally script an entire day of panels that fit with your company’s narrative for a higher ROI than trying to get in front of someone else’s audience for just one panel. It’s more work, sure, but it’s potentially a much more valuable outcome. Besides, if you really are the industry leader you say you are, shouldn’t you be running the go to industry conference?


The most valuable career asset I have is my weekly newsletter that goes out to the NYC tech community. It’s mostly just a collection of events, but it has grown to include a fair bit of preamble and perspective. Imagine you were going around telling everyone that there’s a new revolution happening in the dating world away from just a solitary swipe right/swipe left perspective—and that there’s going to be a backlash about how dating works today. Then isn’t there at least a week’s worth of articles, links, essays and content being put out there already to fill up a newsletter, not to mention what you yourself might have to say about it? Having a weekly, consistent curated stream of news and becoming the industry’s source for your narrative is invaluable—and can also be turned into an asset for others. You can post events, conferences, and links to what others are saying and doing too.

Setting Expectations

Participating in social conversations and thought leadership as a founder isn’t something that is going to pay off overnight—but consistent contributions to this area has a high likelihood of paying off for your company. On the other hand, being a founder trying to raise money when no one’s ever heard for you or what you’re up to, nor have they ever read up on what you’re saying is going to happen in the industry is starting from less than zero.

Plus, if you never invest in serendipity, it’s never going to happen to you. You’ll never get that speaking opportunity at a conference or you’ll never get that inbound from an investor asking “Hey, I read your piece, let’s meet the next time I’m in NYC” if you’re not contributing to your thought leadership profile. I can’t promise when, where, or how it’s going to pay off, but the best time to plant a tree is twenty years ago, and the second best time is now. Trust me what you’ll wish you had been doing this for the past year when you need something to happen to your company that’s a bit out of your control like fundraising, hiring or launching.

Friday, June 14, 2019 - 12:12pm

I’m getting married today.

At least, if she says yes.

But, assuming that all goes according to plan, I have a few thoughts on how I got here—given that dating and relationships seem to vex a lot of people.

I would say that the most important factor that went into both of us finding someone to marry was that neither one of us felt like we had to find someone to marry to be content. We both spent time developing ourselves and our lives as complete and we weren’t waiting for someone to make us whole—so we entered this relationship not as gap fillers for each other, but as two independent people who chose to be together because it was better, instead of trying to avoid being single.

You don’t need anyone to be content—but it’s very nice to meet someone you want who wants you back.

For me, winning her over was an exercise in self-awareness, patience, and respect. In the past, not only had I been pretty unaware of the other person’s perspective in a relationship, but I thought that getting to the finish line was a function of effort. There were times when I thought I could get someone to like me by trying super hard—by proving I could be the best boyfriend ever, when that wasn’t anything close to what the other person was looking for.

When you find someone who is content with themselves, most of what they’re going to look for in you isn’t how you treat them—I mean, it’s important, but it’s not the only thing. It’s going to be about how you treat others. Aja and I appreciate each other just as much if not more for how we treat our families, our friends, and the authenticity we put into our work than for what we’re doing for each other.

Don’t accept someone that is nice to you but a jerk to everyone else.

A few years ago, I dated someone for whom therapy was an important part of her self development. As part of my development, I decided that if anyone was either critical of me or made a suggestion to me that I would start from a position of acceptance before I was dismissive of it. When we broke up and she suggested that I might get something out of therapy, I went ahead with it. I felt fine and didn’t necessarily have something that I thought I’d get out of it, but I was doing this thing of non-dismissiveness, so I tried it out.

I did one session and in talking about relationships, I realized that while I had tried very hard in prior relationships, I never shifted my perspective to try to understand what it was the other person was looking for in a relationship.

Like, never.

I was too busy trying hard to be nice, to be romantic or loving to focus on being understanding and empathetic. No one wants a bigger version of a gift that they didn’t want in the first place or two of that gift.

It totally changed my approach to relationships (and frankly, was the best free introductory anything I ever did, since I didn’t go back).

Things become a lot clearer when you ask yourself the question, “Am I honestly the person that this person is looking for?” versus “How much do I like this person?” It works really well for someone who, at 39, doesn’t really feel like changing who they are that much—because it’s much easier to answer than trying to figure out if you like someone “enough”.

The last thing that I feel is really important is a realistic sense of what’s important to you.

I’m obviously pretty athletic and into sports—but I don’t really need anyone to do them with me. What I do care about is that it’s going to be ok when I roll out of bed on a Sunday morning at 6AM to go on a ride or do a half marathon.

What I’ve found with myself is that Aja is so accepting of the things that were a part of my life before she arrived, like sports, that I’m more willing to give them up, because it doesn’t become a proxy war for balance in our relationship. When I got asked to play on an ice hockey team this summer, I only signed up for half the games not because she would have had a problem with me playing on all of them—but because it would have been ok.

Frankly, I’d rather spend more time with someone who thinks it’s ok for me to play more hockey than actually playing more hockey.

Aja, I am incredibly lucky to be marrying you today. I love you and I cannot wait to see you later…

… after my bike ride.

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Did the knee and everything... #june14thyesofthisyear

A post shared by Charlie O'Donnell (@ceonyc) on Mar 28, 2019 at 8:14pm PDT

Charlie is a Partner at Brooklyn Bridge Ventures, working on very early stage investments in the "Greater Brooklyn" area, which also includes Manhattan and the other boroughs of New York City.