Thoughts on my Wedding Day


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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 Continue reading “Thoughts on my Wedding Day”

Tiny Checks


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Not every fundraise is easy and sometimes you wind up having to take a higher quantity of smaller checks than you’d like. On the other hand, some people try and pad the cap table with a bunch of big names or industry vets, even if their check size is small, just to build the network. They have an idealized vision of how easy it’s going to be to utilize everyone once the business gets going.

The reality is that the last thing most founders will have time for is writing up investor updates. They’ve got tons of other things that seem more pressing and the last thing they need is a bunch of scrutiny and questions from people who wrote small checks. Not only that, sending out important information in e-mails to lots of people increases the possibility that confidential information gets out.

Still, I think it’s worthwhile to keep Continue reading “Tiny Checks”

The Uber that Never Was


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Using the proliferation of newly GPS-enabled mobile devices to enable taxi hailing and beat out stagnant incumbent providers was always going to be a big win for consumers. It provided a better service than existing cabs were going to be able to do for at least several years—cutting out lots of unnecessary overhead in the system.

Had it been built differently, it could have been a better company and honestly I’d like to believe maybe even a more valuable one in the long term. Maybe it would have given up short term hypergrowth—but as the standard bearer, it could have helped the whole market get on this path, instead of just landgrabbing.

It could have championed fair pay and a national minimum wage—incorporating it into its brand. Would that have cut into its growth? Maybe—but in the long run it would have created happier drivers and a base of more Continue reading “The Uber that Never Was”

The Terribleness of On Demand: Why I Backed Journey Meditation


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When I was growing up, I watched Seinfeld religiously—literally every single Thursday night from the premiere to the end without missing a single one. Not only did I really love the show, but I was that committed to it because of the reinforcement I experienced by being part of a community that also watched when I did. The next day, I couldn’t wait to see my classmates and repeat whatever the key line from the episode was. It was almost more enjoyable to laugh about the episode the next day with friends than it was to watch it on my own the night before.

The other nice thing about live, scheduled TV—something I’ve come to appreciate now—is that sometimes there was nothing on worth watching. I would flip through the channels and if I didn’t find anything to watch, I would turn it off.

When’s the last time you hit Continue reading “The Terribleness of On Demand: Why I Backed Journey Meditation”

Certainty on Demand: How Labor Platforms are Moving to Higher Order Work


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Over the years, we’ve seen a revolution in how labor is supplied because of technology.

First, we saw simple outsourcing—taking one person doing one job and moving the job over to a cheaper person in another geography. That only worked because you could connect everyone via technology—routing phonecalls, e-mails, design documents, etc. halfway across the world so that working with someone in India was as seamless as if they were on another floor in your building.

As emerging markets start to achieve more equality with the rest of the world in labor cost, that arbitrage starts to go away. The best people start to charge more, or they simply move to the US, and the time and efficiency cost of working with lower skilled labor starts to not be worth it anymore.

To gain next level efficiencies, we worked on breaking up the tasks that go into a job. If

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The Smartest Most Unsympathetic Guys in the Room: Tech’s Responsibility Going Forward


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I’m a bit tired of tweeting, donating, protesting, etc. to end gun violence–so I’ll take a different tact in the wake of the Christchurch shooting.

If you’re an investor, employee, or just user of a large media distribution network, please ask the hard questions about the responsibilities of those platforms to prevent the spread of hate and violence–again and again until these platforms take their role seriously.

It’s just not acceptable that violent people see online platforms as a viable channel for their hate and that, after all this time, the “smartest innovators in the world” still seem at a loss as to how to stop it. How many ways have we heard Youtube tell us that hundreds of hours of video gets uploaded to Youtube every second–and they make it seem super easy, but yet they can’t get out in front of people trying to share a mass shooting Continue reading “The Smartest Most Unsympathetic Guys in the Room: Tech’s Responsibility Going Forward”

The Achilles Heel of Startup Ecosystems


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Across the world, various economic development organizations, government agencies, and non-profits are putting in admirable and well-intentioned efforts to develop startup ecosystems. They’re building campuses, districts, buildings, spaces, as well as running new educational efforts and contests—basically anything they can think of to foster the growth of new and innovative companies.

One thing they’re spending very little time on could wind up being the reason why all of these efforts dry up. Very little time and effort is spent helping professional, full time investors raise capital for venture funds. Everyone is excited when a new company gets funded in their ecosystem, but no one spends much time thinking about where the money comes from to fund that deal.

To care about this issue, you have to believe one thing—that the presence of full time, professional investors in an ecosystem catalyzes funding rounds better than a collection of part time angels, Continue reading “The Achilles Heel of Startup Ecosystems”

Three Exercises Every First Time Venture Fund Needs to Work Through


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Some VCs peel off of other funds to start their own and they have the benefit of a track record from their previous firm to show. Obviously, that’s ideal, but that’s not where everyone starts.

If you’re lacking for track record as a firm, here’s three exercises you should walk through to help turn your pitch and due diligence meetings from guesswork into something more substantive.

The Fantasy Cash Flow Model

When I was an analyst at the General Motors pension fund, investing in VC funds, I had to build a model of how I thought they would perform. It started out with initial investment size, pricing, and outcome behavior for each deal and then it made a prediction around the distribution of outcomes.

It’s easy to say you’re going to be a 3x fund, but how does the math actually get you there. If you’re not actually modeling this Continue reading “Three Exercises Every First Time Venture Fund Needs to Work Through”

Some Thoughts and Models Around Ownership Targets


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You hear this from VC’s a lot: “We need to own X% of your company to make our returns.”

They back it up with sensible math—owning 20% of a billion dollar outcome returns a $200mm VC fund, and, of course, you’re trying to at least return the fund. So, no one really questions the ownership model.

Yet, when you buy shares of Apple or Facebook, you don’t even think about what percent of the company you own. How then, do you expect to make money when you’re buying on the public market?

Everyone knows the answer to that.

“Buy low, sell high.”

Seems like that should translate over to the venture world, too. After all, all we’re really doing as VCs is buying shares, aren’t we? How come VCs don’t think about it that way?

There are two reasons. First, price discipline doesn’t work in overly competitive markets.

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Why Investor Titles are Important


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The other day, I generated a lot of buzz and feedback around my assertion that calling yourself an “angel investor” should require a little more than small syndicate investments:

Most people seemed to agree—some disagreed, but a few people were like “Why do you care? What does it matter as long as they’re out there writing checks?”

Some people thought it was a privileged way to enforce hierarchies and to equate money with value—and I understand where they’re coming from. The issue is that nomenclature creates a certain set of expectations that founders use to allocate the most precious of their resources—their time. They want to make sure that they can Continue reading “Why Investor Titles are Important”

Five Questions for Vetting an Investment in a New or Emerging VC Fund


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While most of the money that goes into VC funds comes from institutions that are highly experienced in the asset class, some family offices and high net worth individuals also invest in VC. They’re trying to get exposure and diversification at the same time, while potentially seeing co-investment deal flow.

A lot of VC fund pitches—and I know this because I used to vet VCs for a living as an institutional limited partner at a pension fund—sound the same. They all have great networks, above market performance and some special sauce that sounds nice but you’re not 100% clear it makes sense as a way to boost returns or get access to deals.

Here are five questions I would ask any new or emerging VC fund:

  1. In the five years before you had this fund (in case they have a short track record) what deals could you have legitimately gotten Continue reading “Five Questions for Vetting an Investment in a New or Emerging VC Fund”

The Tech Issue that Matters Most in NYC


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The headlines in the tech and startup world have not been good over the last couple of years. As it turns out, the “move fast in break things” culture was itself pretty broken—full of discrimination and harassment. On top of that, the rise of tech is exacerbating wealth inequality, creating some serious data privacy issues, and allowing hate and misinformation to grow rampant on its platforms.

For all its promise of moving humanity up and to the right, the tech industry boom has had some nasty side effects, and as we saw in Amazon’s HQ2 fight in NYC, a lot of people aren’t taking it anymore.

It’s not surprising. When wealthy tech leaders seem, at best, disconnected from the rest of the world’s issues and at worst totally unsympathetic and wrapped up in their privileged little bubbles—it’s easy to be against them.

Lessons from a Diverse Venture Capital Portfolio


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Brooklyn Bridge Ventures, the pre-seed and seed stage VC fund I run in NYC, has invested in 64 companies in the last six and a half years.

Twenty-five of them have at least one female co-founder.

Fifteen had co-founders over 40.

Five have LGBTQ+ founders.

Three teams have African-American founders.

Three of the founding teams are married couples.

All were backed based on the sole criteria that they had the potential to make my limited partners a lot of money. The diversity is the direct result of our mission—to build the most accessible venture capital fund in NY. I don’t require warm intros. I will back a wide variety of types of companies—everything from The Wing to Imagen.

Surrounding yourself with diverse teams means being exposed to a lot of different perspectives and creates learning opportunities not possible when everyone you deal with professionally looks and acts like you Continue reading “Lessons from a Diverse Venture Capital Portfolio”

The Potential for Fraud Caused by the Unnecessary Mystery of the Family Office World


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About a year ago, I received a LinkedIn connection from Richard Briggs—a Brooklyn Law Grad who spend 25 successful years at Lehman and was operating his own family office. He knew a bunch of other VCs in NYC and seemed like a great potential Limited Partner connection.

There was only one problem. Richard Briggs didn’t exist.

No Richard Briggs ever attended Brooklyn Law and none of our mutual connections had ever met him or interacted with him. He was a completely invented person—and no one connected to him on LinkedIn ever bothered to check.

I guess it’s pretty easy to get VCs to think that you’re a rich person interested in investing in their fund.

Just the other day, I got the following note:

Dear Mr. O’Donnell,

I am writing to you on behalf of Mr. SM Karabel (Chairman) of “Karabel Family office” which is a large Palm Beach based

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Sevens Don’t Get Funded


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Ask any VC how excited on a scale of one to ten they are about their latest deal, and they’ll tell you eleven out of ten. Veterans will probably be a little more cautious and tell you they’re at a ten out of ten—but despite knowing all the risks, a VC simply isn’t going to get over the line unless they’re pretty blown away by an idea.

That’s because of the simple math of competition. I get 2000 things passing through my inbox in any given year, and I make about ten investments per year.

How excited do you think I am if I’m only picking the top 10 out of 2000? Do you think any of those handful of deals are seven out of ten? I see TONS of sevens—and they’re often the hardest ones to pass on. They’re nothing necessarily wrong with them. The team is good. The Continue reading “Sevens Don’t Get Funded”

Preparing to Start a Company


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It’s that time of year again—the season of people quitting their jobs soon to start a company. I don’t know whether it’s New Years resolutions or end of year bonuses, but I feel like there’s a bit of a peak in people wrapping up previous things looking to start something new.

If you’re going that route—here are a couple of things I would suggest:

  1. Have at least six months of personal expenses in the bank—and that’s only if you know you can at least get some angel capital based around your connections to investors, friends, family, etc. It should take you at least that long from having an idea before the idea is fully vetted in order for it to be worth investing in. Sometimes it’s shorter, but you always want to be conservative in this case.

  2. Understand where similar companies have struggled and tackle that part first. If Continue reading “Preparing to Start a Company”

Startups Need to Diversify Away from Paying Facebook


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Over the last five years ago, a disproportionate amount of venture capital funded paid acquisition on Facebook.  Some very large consumer facing businesses were built, but that gravy train won’t last forever—and signs are that it is seriously slowing down.  Companies are reporting that acquisition costs are trending up, and optimization is increasingly feeling like squeezing blood from a stone. 

Having 90% of your marketing dollars go not only to one channel, but to use just one company’s platform is always a risky strategy—but now, in particular, it feels like Facebook is at a serious crossroads.  Not since it’s pre-IPO days has the company looked so vulnerable. I’d even argue that the company’s continued attention dominance has more to do with the ineptitude of Google and Apple to build compelling consumer facing software than the quality of what Facebook is doing.  The core Facebook offering is declining in usage Continue reading “Startups Need to Diversify Away from Paying Facebook”

There are Right and Wrong Ways to Add Amazon to NYC


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I’m not a fan of protectionism.

If I’m going to call it out when Donald Trump does it, trying to block the flow of free trade with tariffs, or block the flow of people through immigration bans, then I should be consistent about it on the local level. I would never say that one company shouldn’t be free to expand to a new city.

That being said, I don’t like paying people to do anything they were going to do anyway—and this is especially the case when it comes to economic incentives. It bothers me, for example, when condo builders get tax incentives to build luxury condos in NYC when it’s pretty clear you can still make plenty of money without them—and it’s not like they would pick up and start building condos in West Virginia if they got better tax treatment.

So when it comes to Amazon’s “HQ2a”, my Continue reading “There are Right and Wrong Ways to Add Amazon to NYC”

How to Run a Tech Conference in NYC


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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 Continue reading “How to Run a Tech Conference in NYC”

Shut Up and Invest? Investors Weighing in on Politics


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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 Continue reading “Shut Up and Invest? Investors Weighing in on Politics”