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Charlie O' Donnell

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Monday, November 12, 2018 - 10:32am

Over the years, I’ve spoken at a bunch of NY tech conferences—and they vary widely in terms of their success.

A few things remain consistent:

  • Organizers complain how difficult it is to get people to show up.

  • Attendees don’t stay.

  • Even when they do stay, they’re not super engaged.

Here are a few tips for organizers if you’re going to put on a conference here. It’s very possible and I’ve been to some good ones—and the best ones all have some common attributes.

The biggest thing that conference organizers don’t seem to understand is the following:

New York City is not one tech community.

New York is a multi-industry town. We have media startups, healthcare startups, real estate tech startups, fintech startups—every kind of startup you can imagine. The advice, connections, and customers they seek are in all sorts of different verticals, and so it’s unlikely that you’re going to be able to build out a conference where paying hundreds of dollars and spending a day makes sense to someone if only 10% of the content and audience is relevant.

That’s become even more true as startup content flourishes online. In NYC, more and more people have joined startups, so they’re more familiar with the basics. Ten or twelve years ago, you could do a generalized tech conference about the “101” of startup life and a lot of New York founders would get a lot out of it, but now we’ve basically all gotten up to speed, read the posts, watched the videos, etc.

The only way to do a conference here that isn’t vertical specific is to make it about a horizontal—something that all startups have on their todo list that they find difficult, like fundraising, recruiting, marketing, etc.

And if you’re going to do a fundraising one, it needs to have real check writers—partners from known VC funds with deals in their track record people know. It’s ok if you get the occasional principal, but the majority of the speakers need to be people who could lead my deal that I wouldn’t otherwise be able to access. Analysts and associates aren’t difficult to access and they have less experience—and while they’re a smart bunch on the whole, they’re just not going to be a big attendee draw.

The other thing about conferences is that, in general, they aren’t very good—for either the audience or the participants.

People are growing tired of not only the format, but the lack of work actually put into the content itself. There’s a lack of research and vetting that goes into topics, and panel moderators fail to create narrative. Moderating is a skill. Invite people people who are good at it, or train them.

A few tips for panel moderators:

  • Know what you want the panel to say before you ask it. Create the narrative you want to share beforehand, and select your panelists and questions to reflect that.

  • Ask questions that will get at meaningful, specific answers. Don’t ask, “What are you seeing?” or “What’s exciting to you?” because the question is too open-ended to be weaved into a coherent narrative.

  • Don’t ask any question to more than two people on your panel, regardless of how many people are on your panel. You’re better off with less answers to more questions than the other way around, so bounce around, directing questions to specific people they’re most relevant to. After two, the answers get repetitive—and there’s nothing worse than a panelists wasting time with a “I agree with everyone else here” or “I don’t have much to add, but…”

Also, why does every session need to be a panel? Mix up the formats. Ask key, experienced attendees to lead small group sessions. Leave more time for hallway conversations.

Curation of attendees and speakers is incredibly important—which is why you really need industry insiders to be in charge of the content and speaker invites. Just because someone raised a round or two of capital doesn’t make them a great speaker with a compelling narrative—nor should they be asked how to run a successful startup, because they aren’t successful yet. Vet panelists and topics with the kinds of people you’d love to see at the conference before you invite anyone.

Diversity is not difficult—you just need to want it.

There are a ton more interesting people with unique perspectives on a topic that aren’t all straight, white and male. Just because they don’t sign up right away doesn’t mean it’s too hard to find them. Reaching out to communities of women and/or color with specific invites will help—as well as making sure these potential attendees can see people with similar perspectives participating at high levels at the conferences

If you want influential/VIP type attendees to stick around at the conference, you have to give them something to do. If someone is speaking at 2pm, they’re not going to necessarily come for lunch unless they’re captaining a table conversation. They’re not going to stay after unless you’re organizing some people for them to meet.

Every conference needs a Code of Conduct. Here’s one that I used previously. There’s no better way to empower victims of bad professional behavior than to explicitly state how people should behave, giving clear indications of organizers wanting to be aware when people step over the line..

Lastly, logistics is important to NYC conferences. If it isn’t near a subway, you’re going to be hard-pressed to get anyone to attend—unless you’ve already got a community following or you’re an oversubscribed conference to begin with. First year conferences really need to focus on lowering the barriers to participation.

Monday, November 5, 2018 - 10:11am

For the last two years, I’ve been pretty vocal about politics on social media, in my weekly tech community newsletter and on this blog.

As I’ve gotten older, I’ve gotten more progressive—which is a big shift for me because I grew up conservative. More and more, I’ve felt the need to speak out—but the question was asked of me recently whether or not it does more harm than good for me professionally.

It’s an entirely fair question—and the risk is that limited partners, founders, or other VCs might not want to work with me because I’m vocal about my political views.

Most people don’t think about it, but VCs need to raise money from high net worth individuals and institutions to have the money to put to work. These groups are much more likely to be more conservative than your average NYC or SF tech entrepreneur. (I mean, just about anyone is more conservative than the average tech entrepreneur, so it’s not exactly a high bar.) I suspect, though, there are even some founders out there who could be put off by the things I write and probably how I write them.

As a solo General Partner, my firm is me—and there isn’t a difference between investor Charlie and personal Charlie. When you get an investment from Brooklyn Bridge Ventures—you get me. When you ask me what I think about something—I’m not juggling two hats. My investment thesis is shaped by the sum of my personal experience and so are my values. My goal is to make Brooklyn Bridge Ventures the most accessible VC firm not just because I think it’s good business, but because I think it’s a based on good values. I don’t believe that your gender, school, socioeconomic background, race, identity etc. has predictive value for whether or not you can be a successful founder—and I think the next great 50 companies are going to be majority founded by people not in anyone’s “inner circle” today.

I also believe in treating people with respect and being helpful when I can—treating the world like a community where we all benefit from generosity and things aren’t always zero sum. These are both my business principals and my personal values.

The struggle I have with politics these days is that it doesn’t quite feel like a discussion of principals anymore. If you want to sit down and debate what the size of the government should be those are arguments I’m happy to have and can stay pretty respectful around.

But I don’t think that’s where we are today. It’s hard to ignore that some policies aren’t just disagreeable or not optimal, but they just seem, well, wrong. They feel wrong because they violate some basic values I think our country should be built around. They’re wrong because they seem more like power plays than positions—inauthentic political theater. They’re wrong because they’re clearly not working, or they’re only benefitting the privileged at the disproportionate expense of everyone else.

I understand that when you draw a right/wrong line, it makes people feel alienated and unwilling to engage—no want wants to have their values questioned.

I used to think that—that you could concede and negotiate in the search for common ground around values. For example, I used to debate the best tactical way to get to marriage equality—because I didn’t think that people in Arkansas or wherever were “ready” for it, and so I would say we should go state by state first, showing people that it wasn’t the end of families as we know it, and eventually have it spread everywhere

That was before I thought about what it would be like to be gay in Arkansas—and how sometimes tolerance of things we see as wrong can be just as bad as the wrong in itself, empowering those who would discriminate. Today, I’ve come to realize that calling out where you see injustice and wrong is the better thing to do, even if it offends some people.

Can I prove that I’m right about my opinions? I can’t prove that I’m right about any of this stuff any more than I can single-handedly prove climate change as a non-scientist—but I’m pretty sure we’re fucking up the environment and I’m definitely going to judge you for support of any policy that makes it easier to pollute, because you think climate change is debatable or that somehow economics justifies the destruction of our planet.

But what does that judgement even mean?

Perhaps I’m judging you, but so what? What right does anyone have to live their life free of the judgement of others? We get judged all the time. Limited partners judge my investment acumen. Founders judge whether or not they think I can add value. I judge founder ability and the level of homework they’ve done on a plan.

A co-op board is going to judge me at my next apartment.

Opinions are a dime a dozen, and if you’re not happy with someone’s opinions or their opinion of you—there’s really only three options. You can either take them to task—because maybe you think they’re wrong and you want to call them out and have a debate. You can just put on your thick skin and ignore them. Lastly, you can usually choose not to have that person in your life.

I’d hate for the third to be an option that gets taken too many times. I wouldn’t want to lose my relationship with my parents just because they’re conservative—no matter how many times we argue. I wouldn’t want to lose an investor because they disagree with my politics—because I strongly believe I can make great returns for them by investing in impactful companies. I wouldn’t want to lose a deal because I know how hard I bust my butt for founders.

But does that mean we can’t talk about it? Is it better to avoid the subject or to have those difficult conversations?

It’s probably going to happen that I’ll lose a few opportunities along the way—but I also think it’s going to happen that someone reaches out to me because of what they heard and wants to work with me because of it. In fact, I know it has. I know I get deal flow because founders want an investor who is going to be direct and tell them what they think—about anything. They want an investor who works from a set of shared values and not purely on a set of economic algorithms—because this is a people business highly short on data to make anyone’s algorithm work that well anyway.

Plus—the values of today’s innovators are getting more and more progressive everyday. They’re looking for better ways to share, to run cleaner businesses, and building more accessibility into power structures. They’re questioning capitalist models as the best solutions to every problem and examining where and how they feel comfortable profiting.

As investors, we’re in positions of power—and as we know from Spiderman, with great power comes great responsibility. We have to be conscious of our privilege and try to use our stature in the community to improve the world around us. Quietly sticking to investing means wasting the opportunity to do good. You should always feel comfortable talking to an investor about their values and their politics—and you have every right to work with people on the same page as you, no matter which side you support.

Monday, October 22, 2018 - 11:15am

In almost every single investment I’ve ever made, I can think of a singular moment in my relationship with a founder that, no matter what came before or what might come after, defined our relationship. Often times, it came in a very vulnerable and down moment for the founder—perhaps they just lost out on a big opportunity, had someone from the team leave, or they’re running low on capital before sales have come around. It happens to everyone regardless of how well the company is doing—because no path to success is a straight line.

While it might be a low point for a VC’s expected return on investment, it might demand of an investor a high point in their generosity and empathy—because a founder is going to remember who was there for them with confidence and motivation, and who either abandoned them or tried to take advantage of the situation.

Not only that, but the venture community is extremely small when it comes to investor reputations. Founders are tremendous advocates for investors who have their backs—but if you put a founder through the ringer unnecessarily, everyone in their circle is going to know about it, if for nothing else because they’ll need to talk through it with others in real time for guidance.

The key to having difficult conversations with founders is setting expectations. The worst thing you can do as an investor is to go back on indications of support or to blindside a founder that you’re changing the strategy around your professional relationship. If you’ve lost the confidence needed to follow on in a deal, that needs to be signaled right away. If you’ve decided not to invest in the first place, you need to say so as soon as you know it so you don’t string a founder along. If you’ve left your firm or have other deals that require more time, you can’t just become a ghost or check out on a founder after negotiating all sorts of legal incentives for the founder to be motivated for the long term, which makes someone assume you’ll be doing the same.

Failure stories are going to be told just as often as success stories—and investors need to make sure that even when the decisions are tough, they come early, consistently, and with transparency, or they’ll be one of the villains in an oft-repeated tale.

Monday, October 15, 2018 - 12:55pm

Being a founder means showing confidence. It’s nearly impossible to fundraise, hire, or lead without it—but at the same time, founders don’t know everything.

There are many things they’re going to be doing for the first time that are ridiculous to expect them to know how to do right off the bat. Just because you start a company doesn’t necessarily mean you’re automatically a good manager, a good recruiter, or good at PR. Yet, you’re under constant pressure to instill confidence in your team and your investors that you’re the right person for the job. Raising your hand to say that you’re struggling with something isn’t easy, but it’s a crucial job requirement.

The most successful founders excel at one thing more than anything else—learning. They ask a lot of questions and listen, putting into place best practices and systems that don’t depend on them just knowing everything outright. For example, instead of thinking that they have to be a great manager, knowing at all times how each person in the organization is doing, they put systems of evaluation in place that are both quantitative and qualitative so that everyone can be on the same page about job performance from a more objective point of view.

Systems take the pressure off individuals for lots of different aspects of the company. They allow everyone to know what their part is and how they’re going to be measured. They also help switch the conversation from “This person is good or bad at X” to “This is how we’d like to do things here and here’s how you’re performing compared to that.”

If a founder has issues with confidence, admitting they need to work on things can feel like opening old wounds of the worst things you think about yourself. You’re already convinced you’re not good enough, and so being asked to examine how you can improve can feel like a painful, all too well-trodden path or a slippery slope to feeling like you’re not good at anything. This is where it’s important to check yourself and be confident about what you bring to the table, while being objective and constructive about where you need some advice, a system, or training to help you perform better. No founder is perfect, and if you find yourself funded, employing people, and having already launched—you can’t be as inadequate as your worst insecurities tell you that you are.

Trust me, you’re not that good at faking it.

You’re an early stage founder with lots of potential and you’ll become a great executive one day if you’re willing to learn.

Tuesday, September 25, 2018 - 12:28pm

I started a company back in late 2007. We raised $550k in seed funding and, despite a lot of hard work, things didn’t work out. It turned out I wasn’t such a great product manager, the technical things we were doing were about two years too early—about to be made orders of magnitude easier by a lot of cloud and big data tools, and, oh, yeah, Lehman went under when I was pitching VCs for money in 2008.

Because we hadn’t raised much money, me and my co-founder didn’t take much in salary—but as things started to look like they weren’t going to work out, we took less and less. I was optimistic about my financial situation because I was in a relationship with someone graduating law school who I thought I was going to move in with. I was just bridging to the economics of scale of couplehood—at least, that was the plan until the relationship ended. That’s when things really went off the rails and my debt started to pile up.

The hardest thing about that situation was that there wasn’t anyone to talk to about it. Personal finance is a thing that no one likes to talk about. It comes with a lot of shame and embarrassment—that somehow if I was more successful or more savvy I wouldn’t be in this situation. I definitely should have saved up more—but I was also embarrassed that I wasn’t more successful at my startup.

What I did do was to create some boundaries for myself. I wasn’t going to sell my apartment and I wasn’t going to sell my car, nor was I going to touch my 401k. I was done when my credit card maxed out and my personal savings were both gone and that was it. When I joined First Round Capital in October of 2009, I limped in with about $31,000 in credit card debt and no immediate savings.

The reality, though, is that the salary I made isn’t realistic for everyone. If I had kids, I wouldn’t have been able to make it as long—but if I had kids, I probably would have raised more capital and just taken more dilution to cover that.

One of my investors made us feel like taking any salary whatsoever wasn’t enough sacrifice—and that they wanted to see us forgo salary until we launched a product. In hindsight, we probably shouldn’t have taken on that investor—because anyone that things that starting a company should be an exercise in putting thumbscrews to founders to create the most painful exercise possible to get the best results just didn’t share our values. Maybe that was their experience, or how they were best motivated, but that’s not how we worked best and you want to make sure every aligns on how to get the best effort from the team.

Founders need to feel empowered to build companies on their terms—and they should seek to find investors who align with their values. Your salary, what you pay employees, work hours, etc. are all very personal decisions for team members and there is no single formula for success.

Generally speaking, I back founders that I trust to understand that any money they take is money the company doesn’t have, while at the same time being self aware enough to know how they do their best work. If you cut your salary to $35k and you can’t afford to pay your rent or feed your kids, that’s not going to get me and my investors the best return on our money. It’s only going to exacerbate a long, slow, stressful death for the company because you were too stressed to make the right decisions for the long term value of the business.

If you’re in NYC and you’re interested in having a transparent and honest conversation about founder finances, check out the Financial Gym and their event on this difficult topic this Thursday. They’re a financial wellness company that I invested in built around eliminating the fear and shame around money and staffed with trainers who are experts in having honest and non-judgemental conversations.

Wednesday, September 19, 2018 - 1:07pm

You’ve got a great resume. You went to top schools, trained at a prestigious bank/consulting firm/etc, and you’ve succeeded in the corporate world doing some important and impactful stuff. Now you want to take that skillset over to the startup world and you’ve got a lot to offer. You can bring some serious business chops to a company that is going up and to the right but needs to take it to the next level.

Unfortunately, there are a few hurdles in your way:

1) It’s very difficult from the outside to identify which companies are for real—and also which are at the stage you’re looking for, which is out of the “might not be around next year” stage, but not already a unicorn.

2) You’re not a specialist—so a company at that stage would be hard pressed to hire you as a head of sales or marketing, for example, because there are plenty of people out there who already have that specific skill set with startup leadership experience behind it.

3) You’re at a point in your life and career where you’re not about to chance things on a company that might not be around in six months for zero salary.

These are all reasonable points—but the difficulty is that you’re part of a marketplace of talent where you’re in the mix with lots of other people with, at first glance, similar backgrounds. They’re willing to take a lot more risk for earlier stage positions, getting into companies before anyone has a chance to see if they’re going to make it, leaving very few opportunities open by the time they get to a stage you’re more comfortable with.

Still, these kinds of positions do open up occasionally—opportunities to lead new business units as General Managers, Heads of Business Development, COO’s, etc. The key is to be “nearby” to the opening when it comes up—to somehow be a known and trusted quantity, not just a resume. As investors, we do make these introductions to companies, but we do it with people that we can vouch for.

Accomplishing that means understanding how the key stakeholders, like founders and investors, spend their time. These folks are super busy and have learned to have a really high bar for 1:1 meetings. They’re not just grabbing coffee with any random former McKinsey consultant who wants to “get into the startup world”. If they did, they could fill their schedule with just that—that’s how many such requests they get.

You’ve got to bring something valuable—like talent, money, or visibility.

If you start making introductions to founders based on openings they have, that’s going to get you in the door. I mean, what’s the point of having a Harvard MBA if you can’t connect someone to the very best professionals. Same goes for business opportunities. If your classmates are running various groups within the kinds of companies these people want to work with, you can be an invaluable resource.

Why stop at classmates? If you know that someone from your school or extended network is a lot more senior to you and is seriously influential in a company that lots of startups would want to work with—why not host a meal or event for them to showcase what they’re working on.

Who wouldn’t accept an invite to “A networking breakfast where 7 midstage startups will be able to give short demos to the CEO/COO/Head of Business Development/etc for Big Interesting Company X that has huge reach/distribution/userbase, etc.” Maybe make it sector focused and bring in a bunch of such contacts. You could ask a bunch of VCs who would be relevant for those companies—and only ask that you bring Series A/B and beyond companies to the mix.

Now you’re offering value ahead of making asks for your own career—and doing it in a way that doesn’t require me to have to go for coffee (or in my case, tea) ahead of time with someone I feel like I’ve met a bunch of times before resume-wise.

Money works this way, too—and it’s a way to get in with VCs, especially smaller funds. Smaller funds are always looking for limited partners and co-investors in their deals—so starting an angel group or just being willing to make such introductions in your network goes a long way. You could run the same kind of group suggested above on a regular basis as a way to network with investors.

The point is, you’re aiming to build trust and show that you’re willing to offer value before asking for it. That’s what a founder and investors want to see with a senior businessperson before seriously considering them for positions. They want to know if this person can leverage their network in interesting and smart ways to create opportunities for the company.

Media is a great opportunity for companies as well. For those that want to also create visibility for themselves in the process as a smart and connected executive, how about creating a podcast or video interview series about “Hires that took the company to the next level” or “The next Unicorn”—i.e. the types of companies you want to be talking to. The secret to asking people to interviews is that they largely don’t care what kind of following you have—because they can always link to the interview in front of their following. So, worse comes to worse you’re just an outsourced segment producer for their content—and eventually with enough links, you will have that following. That’s basically the story of the 20 Minute VC—a random 20ish year old just started asking VCs to be on a podcast and, yada yada yada, a couple of years later he’s out with his own fund. The best part about this format is that you don’t actually need to be an expert—you just need to be able to ask good questions.

What this does for you is that it accomplishes the filtering mechanism as well. Instead of asking people “Who should I network with” which people really don’t have time to think about, you’re asking “Who would be interested in this opportunity I have—it’s only open to companies with at least X number of employees, funding, stage, etc. and we’re really trying to bring impressive up and comers to the table.”

Of course, you don’t have to take any of this advice. You could just e-mail me and other investors with your resume attached, request my time to help you (a one way street), and ask which companies are likely to be near riskless, high upside opportunities for you to get lots of employee options in.

Good luck with all that.

Wednesday, September 12, 2018 - 4:33pm

Whether you’re going through an accelerator or you’re at some kind of speed dating event, short “office hours” meetings present both an opportunity and a problem for investors. It’s a great way to get out from behind the e-mail and actually meet people face to face.

However, it’s a terrible way to get your whole pitch in. There’s just not enough time to convince someone to invest and have a productive back and forth.

So what do you do?

First off, change the goal. The goal is to get another meeting, not to get a check. That starts with the basics. Be professional and polite. A quick thank you for having them make the time is appreciated, especially because they’re likely doing this for a few hours straight.

It’s exhausting—so be excited and upbeat about what you’re doing.

Start off by sharing a quick plan for the 20 minutes:

“Here’s what I’d like to do… First I’d like to establish whether or not we’re the kind of company you would consider and then I’d like to outline the X number of things I think you’d need to believe in order to want to take another meeting with us.”

Describe the nature of your company in terms of stage, sector, etc.

“We’re an enterprise SaaS company solving X problem using Y solution. We’re pre-revenue and we have a team currently building a beta product that will be launched in four weeks. Is this a stage and sector that is a fit with your fund?”

If the person says no, you could ask them for suggestions on who you should talk to, or ask them their best piece of fundraising advice, or frankly, just give them their time back. You could say, “I’m going to e-mail you a description of what we do and a deck—should you meet up with any relevant investors, please feel free to pass this on.”

If they say yes, distill your whole pitch down to a few short things that an investor would need to believe to want to know more.

“For you to be interested, you’d have to believe the following:

That people are willing to pay to protect their privacy online.

That we have a team capable of user acquisition at scale based on our track record.

That the market size justifies venture financing.”

If they take an issue with any of your points, just share with them why you believe you’re right—but don’t try to debate it. You don’t have the time for that.

If you have time, share something interesting about how you do what you do—which, you can of course weave into the answers above—but 20 minutes goes really quickly. With some time left on the clock, ask them if you believe this warrants a deeper dive in another meeting. If they say no, just thank them for their time and move on.

Tuesday, August 7, 2018 - 2:11am

You may have heard that NYC is potentially going to cap the number of cars with Uber and similar services.  

On one side, Uber is adding more cars to already congested streets--and taxi medalians have been capped for years.  

On the other, you'll hear that Uber solves the transportation desert problem in NYC and also makes live easier for riders of color who are used to getting skipped over for rides.

I'm not there yet on whether I have an opinion as to what the right number of Ubers should be in NYC, but I do have a very strong opinion as to the treatment of drivers and other "gig economy" workers.

You see, Uber drivers, Taskrabbits, Relay bike delivery people, etc. are all 1099 workers.  Each individual trip and task is treated as a gig--a one-off project not unlike the way you might, for example, pay someone to design your website or code up an app.  

The problem is that 1099 offers near zero in the way of worker protections for anyone who does it like a full time job.  So, while a W-2 worker has protections around overtime and being overworked, 1099 workers don't have any.

I spoke to an Uber driver the other day.  He talked about the way Uber's rules deal with driving time versus total time.  Uber has a 10 hour limit on driving time--i.e., time on the clock with a rider--but up until recently, had no limit on the amount of time you could drive around trying to get to that 10 hours.  He said it would often take 15 hours to get 10 hours of rider time in.

A W-2 worker would have protections around 15 hour shifts and overtime requirements, but 1099s are SOL.

On top of that, when you take expenses into account like gas, leasing, and insurance, drivers are making below minimum wage.

It's been said that the city is considering putting in minimums for drivers, and I would say that before we cap the number of cars, we should be improving the lives of drivers.  Let's measure time in the car and make sure drivers are *netting* at least the minimum wage for all the hours they're in the car, because you literally can't earn the income without paying the expenses.  

This way, we focus on the first step of making sure Uber and others find a viable business model that doesn't involve abusing its workers.  Then, if it finds it can still exist, then we should figure out how many cars there should be. 

Interestingly, one of the ways it can do this is by increasing utilization--i.e. putting less drivers on the road, increasing wait times, so that each driver spends more time getting paid.  Right now, it floods the system with drivers to decrease wait times for consumers.  I, for one, would wait an extra couple of minutes if I knew that meant fair pay for drivers.

The City Counsel should use its leverage in this cap conversation to force Uber to pay drivers better.  If they really want to avoid the cap, they should be held to a higher worker treatment standard.

Wednesday, August 1, 2018 - 4:41am

Last September, I was introduced to Nicole Gibbons.  She's the founder of Clare, a modern paint brand that launched today to completely reinvent the paint shopping experience. 

She came in and shared all of the hassles that make buying paint a terrible experience--the difficulty in picking colors that actually look good with microscopic swatches, the need to go to a store and crossfit your way home with heavy paint cans, not to mention the harmful chemicals that are in so many paint brands.

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She knew all this from being an influential interior designer and detailed how she believed there was a big direct to consumer brand to be built in the space.  

Her plan was to close a bit first, first picking up $800k to start executing, and then fill out the rest.  

I asked her how far she could get with it--and which milestones she'd be able to achieve.  It only got her a handful of key features related to what she wanted for Clare.  I encouraged her to go out for the whole thing right off the bat.  

To a solo, first time, non-technical founder, asking for $1.6mm may have seemed like a lot to ask for for a Powerpoint--but it was so much better of a plan than launching something half as awesome for half the money.  Talking about a stepped raise can confuse an investor (and we are easily confused) as to what amount of money matches up with what goals--when the founder knows what they really need. 

It's so important for investors to recognize that different founders have lots of different views on how aggressive or conservative to be on a pitch--but underlying that sales strategy is a *real* plan that the founder knows they could succeed with if they could be successful with fundraising.  As an investor, getting at that without knocking the founder for their interpretation of what you want to here is the key to getting some under the radar deals that others might have overlooked.

Well, not only did she raise that money for a full launch, but she was *oversubscribed* and picked up some amazing additional investors like Imaginary, First Round, Able and Bullish, as well as the founders of Casper and Harry's.   

I'm excited to support Nicole, one of the most inspiring and dynamic founders I've met, and to be along for what promises to be an exciting and impactful brand in a huge space.  

Tuesday, July 31, 2018 - 1:37am

Decided to follow no more than 250 people on Twitter. If you got bumped, blame @willyf, who just made a good case for me to follow him. :)

— Charlie O'Donnell (@ceonyc) June 30, 2008

Just about 10 years ago, I tried hard to keep my Twitter follows to a manageable amount--to people I actually cared about following and either already knew or wanted to get to know in person.

5000+ follows later and I've failed miserably.  

It wasn't my fault, though--because the app itself, like all social networks, succeed around growth.  Every single feature is optimized around growing the userbase and increasing everyone's follower count, which means everyone's following count.  Networks are always telling you who from your contacts has joined and recommends you follow new accounts, even though you still only have two eyeballs in your head and 24 hours in the day.  The end result is that each person's connection to you in an ever increasingly connected network becomes more and more tenuous. 

A few years ago, I went to breakfast with Andy Weissman and he lamented Twitter's "Garyvee feature"--the turning off of the visibility of @ replies to people who weren't following the person you were messaging.  Basically, Gary Vaynerchuk would use the @ feature to message a ton of people at a time as he was scaling his following to try and scale 1:1 conversation as much as possible.  It wasn't particularly scalable as following him became a worse experience.  It was a firehose of listening to him not talk to you and just give shoutouts and the like.  However, when Twitter turned this off, while your stream became easier to consume (and easier for businesses or celebrities to interact with people en masse), it came at the expense of authentic discovery.  You never stumbled into half of an interesting conversation with someone you might want to follow based on the topic.  

There was a time when I thought Meetup Everywhere was going to be the next big thing--a social network that was dedicated to connecting people in real life was going to create a lightweight framework for people to localize the social network experience.  If groups got too big, it would be easy to enable splintering.  I don't know why it didn't take, but I've always lamented the failure of the web to create "neighborhoods" at scale that brought communities together (as opposed to just broadcasting to them like Patch).  

For a brief moment, tech was able to make my world feel smaller and more accessible, but now it doesn't feel that way anymore--and I have a theory that I'm part of a very narrow generation that even cares or notices.

There's an age group where you are old enough not to have Facebook in college, but young enough to be an avid user of tech--and to have used the internet to meet new people, probably through AOL or other forms of chat.  When we used dating apps, they weren't based around double opt-ins.  You regularly heard from strangers.  Ok, so it wasn't a *great* experience, but occasionally you'd find diamonds in the rough--and you had to take some risk around reaching out and getting rejected. 

Roughly speaking, this group probably peaks around 35-43.

Not only did we straddle a unique time in tech, but we also came at the tail end of real life neighborhoods as well.  When I was growing up, I would eat lunch and then run outside to play with my friends.  There wouldn't be any coordination between parents to make this happen.  I would just go ring doorbells to see who could come outside if they weren't already out.  It was just assumed that *someone* we knew--a parent or next door neighbor--would be on our street somewhere to keep an eye out.  

This experience made our local world feel very safe and accessible--where we regularly interacted with new people and made decisions for ourselves on who was safe and fun to play with.  We had positive experiences of meeting new kids and becoming friends all on our own, outside the confines of institutions like schools, camps, or parent organized play groups.  

Now, walking these same streets leaves you with a sense that someone stole all the children.  I'm not sure whether it's screen time or parental fear of abduction, but the kids seem to have disappeared from the street.  

It is this same age group that sought this out online--this same group that used Twitter to meet people and Foursquare to find where their friends were hanging out--in order to recreate the neighborhoods experience.  They built Barcamps and unconferences--semi-permeable spaces that got enough scale, but not too much scale, to facilitate people discovery and high quality conversation. 

I don't think we'll see a new form of social media ever attempt to make this happen again--because I don't think the builders of the next generation of apps ever really had this experience to know that it is missing.  Those that experienced it are now at a different point in their life where they're building families or at least coupled off and not really in network expansion mode.

These days, people gather to play a sport, to protest, to play games online, or to watch something--mostly with people they know are already like minded--and maybe that's fine, albeit a little one-dimensional, but sometimes it's nice just to gather in manageable numbers with people you aren't sure agree with you on everything, just for the sake of gathering. 

Can someone build that in a way that isn't contrived or creepy?

Tuesday, July 24, 2018 - 3:58am

I've seen this so many times over:

A founder pitches a VC, or several of them, and then they come back from that process with all sorts of new strategy goals or worries that they need to be doing something differently.  Nine times out of ten, if you're pitching more than one VC, the advice seems to conflict with itself, and the founder winds up playing Wack-a-Mole trying to figure out what to do next.  

What's going on??

The fundraising process is not intended to be a feedback process.  If it was, you'd run it very differently.  Founders would ask for very specific pieces of advice on topics they thought that particular investor would have some insight into.  Instead they often just dump everything they they know about their company on the VC's lap and ask for any kind of feedback whatsoever, leading to really messy data.  

So why is this feedback seemingly all over the board?

First, let's be clear--when you walk out of a VCs office and don't get a term sheet in the next week or at least another meeting with the partners necessary to make a decision, it's a pass.  Lack of a yes is a no--so anything that firm tells you should be taken with a grain of salt.  They don't want to invest in your company.  Any advice they have for you is going to be a bit broken.  It's a bit like if someone doesn't like ice cream and then says your favorite ice cream is too sweet.  First off, you need to drop that friend like a ton of bricks, and second, making that ice cream less sweet isn't a good idea.  They don't like ice cream--so no amount of sweetness reduction is going to make them happy.  That's not helpful feedback.

Second, the feedback is incomplete.  Since you didn't ask the investor to write you a complete strategy guide, all they're doing is giving you *one* of the reasons they passed.  There could be others--so many others that following up on just that one protest might still not lead you anywhere.  Just the other day, I was talking to a founder who was told by a Series A fund that they normally invest in companies around $125k/month in MRR.  She assumed that by getting to $150k/month, they'd automatically invest.  What that investor left out was that before they were going to write an $8mm check, they'd also want to see a marketing funnel established to get leads, an actively growing sales team that showed that the process could be replicated, and growing revenues within each customer.  Otherwise, one awesome enterprise salesperson in a market where contracts were big and good product would be enough--but no one is going to write a check that big to a virtual team of one business person and some devs.  

Lastly, the most important piece of feedback--the team feedback--almost never makes its way back to the founder.  Sometimes, VCs will walk out of a meeting thinking, "Ok there's no way I'm ever going to fund THAT guy," so they just make something up or make something small into something bigger.  They'll never tell you to your face that you're pretty much unbackable, so focusing on any other advice you got from them isn't going to fix the issue.

How do you solve this?

We're working on something cool at Brooklyn Bridge Ventures to address some of these questions.  :)

Tuesday, July 10, 2018 - 1:22am

Recently, I helped one of my portfolio companies make a VP of Marketing hire.  The founder asked me early in the process if I thought the candidate was good.  

Having not worked with her previously, I didn't know how talented she was firsthand, but what I did have confidence in was that her strategy would be well thought out, and if it wasn't working, she'd analyze why, proactively address it, and describe what steps she would take to find a solution.  She struck me as having an disciplined approach to her job, and over time I think discipline wins over raw talent everyday.

Discipline comes with a reasoned approach--a way of breaking down any situation into component parts, addressing each carefully, and sometimes finding help to address the ones you're not able to handle.  Startup life comes with a ton of variables and if you're not trying to bring order to the chaos, you won't be able to scale your effort as things get bigger.

Discipline also helps take responsibility off of a founder's plate--and that's something every founder needs and welcomes.  When you build in methodologies to your job, the founder that you work for can trust your approach in future situations, and they can make like for like comparisons in your performance over time--essential to oversight and process improvement.

Raw talent, on the other hand, has a limited shelf life.  Things change very quickly--so while you might shine in a particular situation, that approach might not work in your next job.  Someone who is great at writing blog posts might struggle in the shorter form media that has become more popular.  A community manager of fans and users might not have the same knack for inspiring user-owners who are participants in a token-based ecosystem where they benefit from improvements in a system in which they are also stakeholders.  A recruiter who is just really good with software developers might not be able to switch to sales recruiting when needed if they don't come with a disciplined approach that can be tweaked for a new situation.  

Lastly, talent without explanation of approach and discipline can actually just turn out to be luck.  When you hire the person that took X company to success, you might find out that if they can't tell you what it was that worked and why, and the logic of how they approached things when they first started, its possible that the company succeeded in spite of them.  Perhaps they weren't really so much the driver versus just coming along for the ride.  

Tuesday, June 19, 2018 - 12:58am
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Building a relationship with an investor, someone who is drowning in pitches and requests for their time, can be difficult.  How do you cut through the noise?  In this video, I share three ideas for kicking off a relationship with an investor you don't know.

Thursday, June 14, 2018 - 1:34am

Long gone are the days when NYC was just a place to build a fintech company or an ad platform.

In the first half of 2018, we saw Flatiron Health’s $1.9 Billion acquisition, Quentis Therapeutics picking up $48 million in financing, and Paige.ai raising $25 Million--all to fight cancer.  Making cancer treatment easier to plan for clinicians was the goal of a founding team of three physicists who cold e-mailed me around New Years.  They had unique insight into a tool that would save time, reduce errors, and improve quality in cancer clinics.

Part of my criteria at Brooklyn Bridge Ventures is trying to figure out whether the person sitting across the table from me has taken the right path to knowing enough about what they're trying to tackle and is eyes wide open about the challenges ahead. 

Radformation, founded by Kurt Sysock and co-founders Alan Nelson and Elisabeth van Wie, is an early-stage oncology software company that works with state of the art radiation equipment.  They began laying the groundwork for Radformation in 2016, after all three left their jobs working as medical physicists in the cancer clinic.  It was during their time working in the cancer clinic that they saw first hand the frustrations of manually putting together complex treatment plans for patients.  Having this in-depth knowledge as potential users of the product helped them get nearly 100 clinics using their platform in just their first year of having a product.  Radformation's FDA 510(k) cleared software allows clinics to catch errors quickly at the source and automate generation of high quality treatment plans much faster than today’s current manual methods. 

No amount of Googling around on my part is going to catch this team sleeping on what's going on in this space.

Finding this is more rare than you think it would be--as many pitch meetings fall apart quickly, like someone who thinks they're passable in a foreign language until they talk to a native speaker.  

Plus, it's always great to back a team making a positive impact on the world and doing so in a lucrative space.  Over $150 billion is spent annually on cancer treatments in the United States alone and cancer accounts for 1 in every 7 deaths worldwide.  Radformation leverages clinical best practices and advanced algorithms to automate the error checking and plan generation process to create the highest quality plans possible.  In this way, Radformation helps clinics provide their patients with optimal treatments and avoid patient harm.  The software is compatible with a wide range of cancer treatment sites, and generates optimal treatment plans in minutes, expediting a process that used to require hours to perform.

I'm also very excited to be in a deal with The Fund.  I first met Matt Brimer in the Ace Hotel lobby back in 2009 when he was interviewing companies to join his new co-working space called "Superconductor", which obviously became General Assembly.  This will be my third co-investment with Jenny Fielding, who is awesome--first on Homer Logistics and the second being another unannounced deal with The Fund.

Tuesday, June 12, 2018 - 3:21am

Time and time again, I hear how hard of a time startups are having recruiting, especially for software developers.  While candidate quality is sometimes an issue, or culture fit, or some other quality, most of the time the issue is that the company just isn't getting enough people into the top of the funnel.  

When I was a startup founder, I had this same issue.  That's when I had a conversation with Max Ventilla, the founder of AltSchool, who at the time was running Aardvark.  Max was telling me how he was interviewing 4-5 candidates a day, which stunned me.  I couldn't figure out how anyone could fill their calendar with that many qualified people.  His reply was simple--he was outbounding to 5-10x that many people each day.  

Oh.

Yeah, I definitely wasn't putting in that kind of volume.  I immediately started writing a ton of notes each day to individuals that I thought looked promising or who could connect me to candidates.  After a couple of weeks, I had written to 500 people, talked to at least 20, and made a hire, after failing to do so for months.  

The other day, I was in a board meeting and we were talking about the need for a software engineer.  The team already had a lead on board.  I asked the founder how much time they were encouraging their lead to do recruiting--and whether they had made it clear that despite a backlog of feature requests, that they were willing to compromise on development timelines in order to make sure their lead had enough time to personally get involved in recruiting.

The reality is, no one likes getting recruiter form messages.  You'd much rather get a personalized note from the person you're actually going to be working for.  That person, unfortunately, is very busy (mostly because your team is understaffed).  When deadlines are fast approaching, their instinct is most likely to double down on their own hours worked rather than pull back and invest the time into recruiting.  They can't do that forever and you need to remind them of that.  The only way your team is going to produce more in the long run is by growing, not by burning out the few people it has.  It's everyone's job to recruit and it should be something everyone should carve out a portion of their day for.  

When you have a software team of 1 or 2 people and you have the money to grow, each of those people should be spending an hour a day on outreach and interviews minimum.  There are, however a couple of shortcuts that can scale their time:

1) Hire an intern or outsourced person to help with the outreach.  Give them access to this person's account or maybe a version of their name, like first letter at startup dot com.  Your team member should just be sending this person links and a short explanation as to why they found this person interesting enough to reach out to.  Let the outsourced person handle the finding of e-mail addresses and composing of actual e-mails, making any editing adjustments that need to be made, as well as handling responses and interview scheduling.

2) When you do get to the point where you think the person has an interesting skillset and you'd like to get a better idea of where they are talentwise--outsource your assessment to Headlight (A Brooklyn Bridge Ventures portfolio company).  There's no reason why your team members should spend time developing and marking tests when a standardized test has already been created and teams of people who have been trained to assess are standing by willing to jump in.  

3) Collaborate with other companies on sourcing through events.  At Brooklyn Bridge Ventures, we run a series of events called Stackup Talks.  We'll get multiple companies together in the same room sharing brief overviews of their stack--be it the code they use to run their applications or even the marketing processes in place for their "acquisition stack".  If you think about what your target talent pool would find most interesting, hearing from one company isn't nearly as interesting as getting a taste of several companies and how they're using the same tools they work with everyday.  Add to that having that conversation in a way that's about the code and the people, not about recruiting, even if you know they're actively hiring.  This Wednesday, we have three companies joining us to talk about React and React Native.  For the time and effort it takes to give an overview of what you're up to, being able to share your stack with 50 or so talent leads is a great use of ROI, making events a really efficient means of connecting on both sides.

Tuesday, June 5, 2018 - 12:39am

I was talking to another investor the other day about the stress that surrounds the ups and downs of the job--winning and losing deals, and having some companies succeed versus others going south on you. 

I shared with this VC my secret to keeping stress at bay: 

I concede the fact that the possibility exists that I'm not good at this.

My fund performance is positive and things seem to be going in the right direction--I've been fortunate enough to back a lot of interesting companies--but there's a lot of uncertainty still.  The possibility exists that things might not all turn out in the end--that I might very well lose investors' money or underperform the market.  

And that, oddly enough, keeps me calm and level-headed.

I find that if you don't admit that failure is a possibility, you find yourself in a situation where your brain can't process even the hint of failure.  When things don't go right, that goes against a feeling of how things are "supposed to" go and your definition of yourself as one of succeeds.  

Stress comes from your inability to accept.  I tell myself, "Despite the fact that I try hard and follow disciplined thinking, I may not have what it takes to create success--and that's ok." 

If you can't handle that reality, you're going to feel some pretty haywire emotions, start misplacing blame, and generally fail to observe reality as it is happening, resulting in erroneous feedback loops.  

When failure isn't an option, you start doing irrational, and potentially dangerous things for your own health and that of others.  It's always an option, because some things just won't work out and you'll need to figure out another plan.

For now, though--you're not there, and you know that because you can be honest about its existence and identifying what it looks like.  That gives you the confidence and the focus to keep at it when you're not there yet and to improve enough to avoid it. 

I can fail.

I might not be good.

I am trying really hard to be better everyday and too succeed. 

All of these things can be true and are healthy things to tell yourself.  

Wednesday, May 30, 2018 - 2:04am

A few years ago, venture capitalists and founders got together to make it easier for international founders to come here and start new businesses.  Why?  Because it has generally worked out amazingly for Americans.  Half of the startups in the U.S. that currently enjoy valuations of over $1 billion were founded by immigrants.  Those companies employ Americans with real jobs--and there's no shortage of dollars willing to back them.  In fact, those immigrants also create more American entrepreneurs--because many people who work for them then go on to start their own companies after their learnings from their first go around.  For example, Max Levchin was one of the Paypal founders (he came here from the Ukraine seeking political asylum, as this was well before the Startup Visa was created.)  After Paypal's success, Reid Hoffman, who worked there, founded LinkedIn, which employs thousands of Americans.

This is such a no brainer rule and there's no legitimate reason to change it.  It's anti-business and it's anti-exactly what even the most conservative Americans want immigrants to come here to do, to pull themselves up by being entrepreneurial and creating value.  Make sure the Trump Administration knows you're against it.  It's going up today and needs your public comments, which can be made here after its up.  

Monday, April 23, 2018 - 11:30am

A few weeks ago, I booked a customized tour of Iceland with Noken, and I did it in about five minutes.  All I had to do was to tell Noken how long I planned to go, what level of hotel and car I wanted, and then I had the option to add on a few extras, and within minutes my entire trip was booked.  I had a connection to my own personal trip concierge and a custom app that outlined my trip.  I literally haven't had to think about it since I booked it--no worries about reservations, what to do when, or doing additional research, things I really don't have the time for.

Some people really like researching travel--and you can spend weeks and weeks doing it.  There is more information on the web, not to mention all the friend recs you can get, than anyone with a full time job can really handle.  For the rest of us that don't have time, and just want to know that someone who does nothing but think about this all the time took care of all this for us--and that our plans, tickets, maps, etc. are all in one place on our phones, Noken us for us.

When I was growing up, we took a few road trips to see my brother in Chicago and then down to Florida, but we weren't international travelers.  My impression of international travel came from Mario Perillo, TV's "Mr. Italy" who used to advertise his family's tour business on NY television all the time...

My grandparents went on one of those tours in the early 80's.  They rode a bus with a bunch of other senior citizens and undoubtedly followed around some guy with an umbrella or flag or something.  That's not something I had any interest in.  

Travel changed a lot over the next few years.  The internet provided a firehose of reviews, lists, and research, which was nice for a while, but then it became overwhelming.  In a world of unlimited choices, curation, transparancy and simplicity became more valuable.

We went from searching millions of recipes to subscribing to meals that someone else picks for us.

We went from comparing every last product out there to trusting single product companies whose value proposition was straightforward and whose customer service was great--whether it was for buying mattresses, sheets, luggage, etc.  

Marc Espana and Emily Brockway, the Co-founders of Noken asked why booking travel couldn't be as simple as buying the luggage for your trip.  Instead of sifting through endless sources of information, why couldn't a company just say "Here, we did this for you".

They built the answer, and all you have to do is hear from the customers to find out the results:

They didn't just set out to make travel easier because it's a big opportunity with nothing else like it out there--they did it to build cross-cultural empathy at a time when that is in short supply.  The events of the last year affected this team personally--being LGBTQ and female founders, as well as having a Dreamer on the team.  It's been shown that the more you travel, the less you think of people who are different than you as your enemy or someone to fear.  One of the best way to make someone more empathetic is to hand them a passport and show them the world and its people.  

Thanks to Noken, there are no more excuses not to travel. 

The tours are an order of magnitude less expensive because the company doesn't have to pay for infrastructure on the ground--it's all in your custom app.  On top of that, unlike almost everything else in the travel space, they're not offering yet another search based route to a commodity product.  They've created something branded that a consumer can be loyal to and come back again and again as new countries are added (they have Iceland and Columbia currently).  The trips are Instagram-worthy, creating viral loops that you simply don't see with the Kayaks of the world.  This addresses some of the acquisition economics that scare some investors away from the travel space, because no one wants to invest in a business competing for the same customer as everyone else with a completely undifferentiated product.  

I backed Noken's pre-seed round back in August.  The funny story about that is that they weren't really raising, but just looking to build connections for their seed.  At the time, I was looking for a company to present to an investor education group that I run to help teach people about how VC meetings work.  When Emily wrote me, I responded by accepting the meeting request, but letting her know that it wasn't just going to be with me--but that she and Marc would be sharing their company like patients in an operating theater, with 30 people in the round listening in on the conversation.  Unfazed, they gave a great presentation and shared how they had done over $100k in revenue, without even having a real app.  It turned out they had been using Invision demo apps the whole time for their customers to use in their trips--and yet still getting rave reviews with only a fraction of the functionality.  

I talked them into taking money from me head of a real round and they've been amazing to work with over the past seven months or so.  I'm excited about their ability to build a seriously large consumer brand in this category in a way that doesn't currently exist.

I'm also excited to see Iceland in two weeks!!

Monday, April 16, 2018 - 11:30am

"I'm not raising right now."

When said to a VC, this is one of the biggest BS lines out there.  You're literally talking to an investor, and if they offered you a big check at a great deal, you'd take it, no?  So, how could you say you aren't fundraising?

On the other hand, some founders *literally* aren't fundraising.  They won't share any info on what's going on with their company, even with investors that are really excited about their concept.

Is this a missed opportunity or just insurance that they're going to put their best foot forward in an organized process?  After all, they have a company to run now and success at meeting your current goals is going to improve your chances of a successful fundraise later, right?

Well, it all depends, right?

Actually, I tend to lean more on the relationship building side, for a couple of reasons.

First, in the early stages, there's a lot more information that can be gleaned about you than we can know for sure about the success of your company.  How you think, what your plans are, etc. are all keys to helping VCs figure out whether they want to back you--and before a Series A, you really don't *know* for sure whether something is going to be a success, no matter how much data you have.  

That's why the first check for a Series A firm is so small relative to the size of their fund.  Think about it... if a $350 million dollar fund leads an $8mm round, they're probably doing about $6.5 million of it.  That's less than 2% of their fund, and of all of their checks were like that, they'd be doing 55 deals in a fund, or over 2x what you actually statistically need for diversification. You think you're getting this big fat check compared to the seed money you raised, but they're actually doing something more like dipping their toes in the water.  It's less signal than you think. 

They know there's not a lot of data yet and it's still more of a flyer, which is why I think putting your head down to optimize your company to 110% to try to get your next round isn't the right strategy--because it's not the mindset the investors are in.  It's a game you're the only one playing.  Not only that, it's a game that you'll never be more poorly equipped to play.  Company success is a function of resources--people and money, neither of which you have much of. 

It's showing up to a gun fight with a Pez dispenser.  

Given that so much of the bet at these early stages, even at the Series A comes down more to "Do I believe what this founder believes?" it strikes me that actually talking to an investor, sharing your vision, and actually starting to work together feels like a better strategy than going silent until "Pitch Day" when you show up all ready and prepared, expecting term sheets in just a couple of weeks.  

This is especially the case with a strong founder who has the best company in a space--because getting to know more investors wards off VCs from investing in your competitors.  You'll clearly come off so much better than them that no one is going to want to settle for second fiddle.  They'd just as soon go find another space where they can find the category leader.  

A lot of founders worry about information sharing.  The fact of the matter is that you're not the only one who has thought about this idea--and you'd have to be pretty egotistical to imagine you had.  What you should imagine is that you're the best team to execute on it--so that no matter what you tell an investor, it won't matter who knows what, because just knowing the plan doesn't mean executing on it.  

One thing going on behind the scenes that founders might not be conscious of is intra-firm dynamics.  One partner might want to meet with you while you're "not raising" in order to build the case inside their firm for doing this deal.  Maybe not everyone in the partnership is there on "Casper for Congressional Testimony Seat Cushions", so they're meeting with you to socialize the idea of the company ahead of you actually being ready for a check.  Keeping close to the vest in this scenario would make it impossible to get the partnership to a yes if you just showed up after running silent.  

Here's something else to consider--the getting to know you phase has very different expectations than the due diligence phase.  If your company is a work in progress and you didn't show up to "pitch" then an investor is absolutely going to understand if you don't have the perfect deck or all the customer acquisition data figured out yet.  Founders worried about this need to stop acting as if investors have never seen a startup before.  

Too often, because most investor conversations result in a no, founders start telling themselves all sorts of reasons what caused that result.  Thinking you were underprepared to discuss your company and that more model tinkering and deck stylizing is just bad thinking.  Investors have seen a wide variety of companies before at various levels of rough edges.  They can recognize a deal they want to be in versus not.

Besides, would you rather get a "no" after knowing that the investor absolutely understood what you were trying to do and you had enough time to share why you were excited, or would you rather walk out feeling like the pitch process was very rushed, and you didn't get everything out there in the shortened cycle you actually had to do the pitch?

On top of all this, what about your own due diligence as a founder?  Don't you want to get to know different investors over time to decide who you want to be working with?  It's like making a hire that you can't fire--so having the chance for multiple interviews over a longer period of time is important and to your advantage.

My advice is to work with your current investors, if you have any, to pick out a short list--maybe three or four investors--and gauge their interest.  See whose eyes light up when you tell them about the company or who gives you a reason why they've been looking at that space.  Have an introductory meeting, and if you feel like you would like working with them, get their feedback on what's going to be important and what should be a priority when.  Do some deeper dive working sessions that give that investor some insight into what it would be like to work with you.  Get them to do some homework for you, too--especially around hiring.  See what kind of candidates they send your way, or what kind of partner introductions they can make.  

Be cautious about your time, of course--cutting off these conversations if you know this is an investor you're not excited about or you're pretty sure they're not excited about you.  

I am convinced, however, that investors come on more because they believe your vision and trust you, conclusions that can only be reached over time through experience, than because you achieved some operational milestone.  

Monday, April 9, 2018 - 11:30am

It's really hard to advise a company when you don't have all the information--and no one has more information than the CEO of the company.  Sometimes, you might believe the CEO is ill-informed, and you're a check on the amount of homework they've done to seek out solutions to a problem, or which metrics or signals they're paying close enough attention to.  That's a really useful function for any kind of advisor, be it a board member, investor, or someone advising about a specific aspect of the company.  

However, it's very tempting as an investor to get into the habit of telling the founder what you think about all sorts of things, before you've asked them for what they would propose as the way forward, or when you haven't even agreed on what's a problem.  

Following this strategy as the CEO means that you're taking the advice of someone who, at best, has 1 out of 30 days of experience with the company via a monthly board meeting, and two, might be pattern matching for a bunch of other companies that isn't the company at hand. 

Lots of different companies operate in lots of different ways--and they've done so across a lot of different environments.  If you started a tech company 25 years ago, you did so before the internet was really a thing for everyone.  If you started one 20 years ago, you did so before broadband was really a thing for everyone.  It was just 15 years ago that no one had smart phones.  It was merely 10 years ago that Facebook hadn't even cracked a billion dollars of ad revenue (It did nearly $40B last year).  

So, even when you're talking to smart people who already built their businesses, they did so in very different environments, with different teams than what you have now.  

As the CEO, you should be prepared to make decisions that you stand by and not have to go to advisors and investors with every issue.  We're here to audit your thinking, not to do it for you.

Here's a good way to do that:

1) Have a way to organize the company's priorities over time and measure results.  

Start with your long term goals, this year's goals, this quarter's goals, etc.  Drill that down to goals for various teams.  This is what's known as Objectives and Key Results.  It's never to early to start using them.  This way, everyone around the table, including investors, management, and employees can see the plans laid out, and have something to weigh in on.  

This way, we can all be standing on common ground and we have an objective way to discuss what's working and what's not.

Processes always trump "gut" when you have the time.

2) Do your homework.

If something seems not right, and you don't know why, you should sit down and talk to a few smart people who've probably been through something like this before--and if you don't know anyone, definitely ask investors.

You're much better off asking investors for resources to do your own research than just asking what the investor thinks.  If nothing else, it helps you build up a network of other founders and executives that you can count on whose experience dwarfs what the handful of your active investors have.

3) Present your observations, findings and proposed solutions.

It's not a useful exercise to just pronounce tactics at a board meeting without context, and certainly not to blindly follow advice because you heard it was something you should do.

What I find most useful is that you give us the opportunity to understand why you thought something was a) important and b) in need of change or improvement.  Hopefully, it traces back to your stated objectives--in which case, it's something we all agreed on prior.

It also allows for an investor to see why you're focused on something and help you with prioritization--because maybe it's not something that actually needs to be addressed right now given your limited resources.  

I want to hear what the CEO thinks first--before I respond to a question.  If nothing else, how else is a CEO supposed to learn the responsibility of setting direction and making good decisions?  It's too easy to just ask others for their opinions if you aren't required to make your case for something first.  

At the end of the day, there are going to be hundreds of decisions I'm not around for as a board member, observer, advisor, etc., and the best thing I can do for a company is help the CEO create a process that makes them the best decision maker possible.

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.