The Willingness to Learn and the Pressure to Be Confident

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 Continue reading "The Willingness to Learn and the Pressure to Be Confident"

Do you have to bankrupt yourself to start a company? How all in is all in?

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, Continue reading "Do you have to bankrupt yourself to start a company? How all in is all in?"

How to Break into a Senior Business Position at a Growing Startup

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, Continue reading "How to Break into a Senior Business Position at a Growing Startup"

How to Rock a Short “Office Hours” Meeting

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 Continue reading "How to Rock a Short “Office Hours” Meeting"

What I Want NYC to Do About Uber

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 Continue reading "What I Want NYC to Do About Uber"

Ask Founders What They Really Need: The Quick Story Behind Clare’s $2 Million Raise

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.


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 raise $800k, which didn't seem like enough to fully build out her vision.

I asked her how far she could get with it--and which milestones she'd be able to achieve.  Continue reading "Ask Founders What They Really Need: The Quick Story Behind Clare’s $2 Million Raise"

How the Need for Growth Failed Our Social Network Experience

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.  Continue reading "How the Need for Growth Failed Our Social Network Experience"

Why VC Feedback is Often Bad Data

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 Continue reading "Why VC Feedback is Often Bad Data"

Give Me Discipline Over Talent Everyday

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 Continue reading "Give Me Discipline Over Talent Everyday"

Backing Radformation: How Many Physicists Does it Take to Build a SaaS Company?

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 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 Continue reading "Backing Radformation: How Many Physicists Does it Take to Build a SaaS Company?"

One Reason Why Your Technical Recruiting Isn’t Working

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.  


Yeah, I definitely wasn't putting in that kind of volume.  I immediately started Continue reading "One Reason Why Your Technical Recruiting Isn’t Working"

Failure is Always an Option

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 Continue reading "Failure is Always an Option"

And then they came for our startups… [ACTION REQUIRED] on Startup Visa changes

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 Continue reading "And then they came for our startups… [ACTION REQUIRED] on Startup Visa changes"

No Excuses not to Travel: Noken is the First Digital Native Tour Operator and Here’s Why I Backed It

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 Continue reading "No Excuses not to Travel: Noken is the First Digital Native Tour Operator and Here’s Why I Backed It"

To Fundraise While You’re Not Fundraising or to Not Fundraise While You’re Not Fundraising? That is the Question.

"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 Continue reading "To Fundraise While You’re Not Fundraising or to Not Fundraise While You’re Not Fundraising? That is the Question."

You’re the CEO.

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 Continue reading "You’re the CEO."

The NYC Council’s Ill-Advised Attempt to Legislate Work-Life Balance Should Be Voted Down

Recently, Brooklyn City Councilman Rafael Espinal proposed a bill last Thursday that aims to make it illegal for private employees in New York City to be required to check and respond to their work emails or take part in work-related electronic communications during non-work hours.  The idea is great--I'm sure everyone would love to live in a world where the moment we walk out of the office, the world just stops, and waits for us to return the next day.  

That's just not realistic at all.  Just ask his campaign staff.  Did he ever send an e-mail to them "off hours"? 

Hard to see how he'd win without doing so.

Don't get me wrong--work/life balance is really really important.  Firms recognize this.  They're doing more and more to facilitate healthy approaches to work, offering meditation classes, paying for gym memberships, creating paths for Continue reading "The NYC Council’s Ill-Advised Attempt to Legislate Work-Life Balance Should Be Voted Down"

An Exercise in Startup Ambition: What’s your ask of Obama?

Given that he doesn't have much to do these days, Barack Obama goes poking around Crunchbase one day and he stumbles upon your startup.  He finds your company, and obviously being super impressed, he reaches out and asks you what he can do to help.

What do you ask of him?  (Or anyone else on that level...)

This isn't an easy answer.  The truth is, you're probably not ready to handle whatever the former leader of the free world can do for you, but you're obviously not going to let this opportunity go, right?  You have to come up with something.

This is a problem of multiple dimensions:

First off, you have to narrow the scope of possibilities.  This is hard.  Obama could probably do just about *anything* for you, but you have to pick one or two concrete things.  You can't Continue reading "An Exercise in Startup Ambition: What’s your ask of Obama?"

Find Success by Helping a Mom Find Success in Your Company

A few years ago, a friend of mine got hired by a company as a software developer.  She was an early riser and liked to get into the office around 8AM.  A diligent worker, she was super focused from the moment she sat down at her desk--and so by the time 6PM came around, she had gotten a lot of work done and ready to call it a day.  

Her young male colleagues had a different approach.  They strolled in at around 10 or 11AM, and didn't really get going for real until about noon.  They spent a lot of time distracting themselves, but worked deep into the night--doing the same amount of work as she did, but stretching it out until 10 or 11 at night.  

Because my friend would take off "early", she got a reputation for not working as hard as Continue reading "Find Success by Helping a Mom Find Success in Your Company"