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"

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"

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"

A Story About Fear, Shame, Expectations and Money: My Investment in The Financial Gym

Today, I can finally announce Brooklyn Bridge Ventures' investment in The Financial Gym's $1.8mm seed round, which I led, alongside Alpine Meridian, Secocha Ventures and several high ranking execs from the finance world.

What's the Financial Gym?

It's a membership based space and service where you can work with a Certified Financial Trainer 1:1 to get financially healthy.  

What's the Financial Gym?

This is the Financial Gym...

The Financial Gym is the culmination of founder Shannon McLay's desire to eliminate the "fear and shame" that comes with financial difficulty--something people are facing more than ever before.  Two-thirds of people in the US have no more than just a few hundred dollars in savingsSeven in ten college grads finish with an average of $40,000 in debt, adding up to a record high $1.4 trillion dollars in total--a 150% jump in the last Continue reading "A Story About Fear, Shame, Expectations and Money: My Investment in The Financial Gym"

A Story About Fear, Shame, Expectations and Money: My Investment in The Financial Gym

Today, I can finally announce Brooklyn Bridge Ventures' investment in The Financial Gym's $1.8mm seed round, which I led, alongside Alpine Meridian, Secocha Ventures and several high ranking execs from the finance world.

What's the Financial Gym?

It's a membership based space and service where you can work with a Certified Financial Trainer 1:1 to get financially healthy.  

What's the Financial Gym?

This is the Financial Gym...

The Financial Gym is the culmination of founder Shannon McLay's desire to eliminate the "fear and shame" that comes with financial difficulty--something people are facing more than ever before.  Two-thirds of people in the US have no more than just a few hundred dollars in savingsSeven in ten college grads finish with an average of $40,000 in debt, adding up to a record high $1.4 trillion dollars in total--a 150% jump in the last Continue reading "A Story About Fear, Shame, Expectations and Money: My Investment in The Financial Gym"

The Atomic Element of Your Marketing

In the last couple of weeks, I've had two similar conversations with my portfolio companies.  They were just starting to build out their marketing strategy and they were faced with the challenge of how to staff it.  Do you hire someone senior who might feel like the execution of the work was beneath them--or who simply hadn't done it in a while?  Or, do you hire someone adept at the actual creation piece, but who needed guidance around how things were strategically put together at a high level?

We had opted to create the high level strategy as a board--since no one knew the companies and their customers better than those that created it and invested in it.  What we realized was that we were in a search for consistency.  What would be the common thread across all of these available channels?

What we needed Continue reading "The Atomic Element of Your Marketing"

How VC Fundraising Favors White Men

Last week, on Martin Luther King Day, I decided that instead of saying something in my weekly newsletter, I would do the opposite--I would listen.  

I asked, "What is your experience of being be black in tech today and what can allies do to improve it?"

The responses I got came at a time when I've been having a lot of conversations with female founders as well about their fundraising experiences.  At this moment, I'm in the process of backing three companies that have at least one female founder and I just finished a round for a black female founder in December.

While being female and being black are clearly not the same thing, they do fall into the category of "not white men", which the fundraising environment favors--but perhaps not in the way people assume.  

This will be the post where I dangerously attempt

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s-l225.jpg
Continue reading "How VC Fundraising Favors White Men"

How VC Fundraising Favors White Men

Last week, on Martin Luther King Day, I decided that instead of saying something in my weekly newsletter, I would do the opposite--I would listen.  

I asked, "What is your experience of being be black in tech today and what can allies do to improve it?"

The responses I got came at a time when I've been having a lot of conversations with female founders as well about their fundraising experiences.  At this moment, I'm in the process of backing three companies that have at least one female founder and I just finished a round for a black female founder in December.

While being female and being black are clearly not the same thing, they do fall into the category of "not white men", which the fundraising environment favors--but perhaps not in the way people assume.  

This will be the post where I dangerously attempt

image1-23.PNG
s-l225.jpg
Continue reading "How VC Fundraising Favors White Men"

The Scariest Thing About Working at a Growing Startup

The amount of work that goes into a job at a growing startup is insane.  As soon as you put one project to bed, three more pop up.

However, the most difficult aspect of the work isn't necessarily the effort required, but the emotions, with fear perhaps being the greatest one of all.

When you're part of a small team, you're indispensable.  You are literally doing three jobs at once--three jobs that should probably be done by two people each.  It's crazy, but there's also a certain security in that.  You won't be fired, because there's no one else to do the work.

As the team grows, however, you're asked to do something most people find really uncomfortable--you're asked to start letting go.  You're asked to document how you do your job, maybe your favorite aspects of your job, and to teach it to other Continue reading "The Scariest Thing About Working at a Growing Startup"

The Scariest Thing About Working at a Growing Startup

The amount of work that goes into a job at a growing startup is insane.  As soon as you put one project to bed, three more pop up.

However, the most difficult aspect of the work isn't necessarily the effort required, but the emotions, with fear perhaps being the greatest one of all.

When you're part of a small team, you're indispensable.  You are literally doing three jobs at once--three jobs that should probably be done by two people each.  It's crazy, but there's also a certain security in that.  You won't be fired, because there's no one else to do the work.

As the team grows, however, you're asked to do something most people find really uncomfortable--you're asked to start letting go.  You're asked to document how you do your job, maybe your favorite aspects of your job, and to teach it to other Continue reading "The Scariest Thing About Working at a Growing Startup"

What Should I Include in a Pitch Deck? [VIDEO]

I've rewritten a lot of pitch decks over time and a lot of them are really bad--mostly because founders have been told what should go in them without a lot of consideration as to why.  Somewhere along the line, someone came up with things that are supposed to go in a pitch without ever asking investors how they take in a story.

Here what I want to see in the video below...

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Here are the notes...

1) Don't keep me in suspense as to what it is.

2) The team slide isn't as important as having the human in front of me, or hearing about your reputation elsewhere.  Team is important, but team slides are boring.

3) Get to the money part soon!  How do you make money?

4) Then, how do you make A LOT of money?  You sell lemonade for 50 Continue reading "What Should I Include in a Pitch Deck? [VIDEO]"

What Valuation Should I Expect in My Seed Round?

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I have to be honest, I'm a little suspect when one of the first questions a founder asks me is about valuation.  So many things about startups are difficult and so few startups raise *at all* versus the number who try, that this seems like not the most important question.

That being said, you want to feel like you got a good deal--and your lead investor should be able to walk you through how they got to a particular valuation and why they thought it was appropriate.  They should be able to provide examples of other deals, and talk openly and transparently about their thinking.

Look, at the end of the day, I'm incentivized to buy up as much of your company as possible, and you're trying to sell as little of it as possible.  On valuation, we're not aligned, but we can meet Continue reading "What Valuation Should I Expect in My Seed Round?"

You Want on That List and Here’s How

With each passing year, we get another set of lists:

Startups to Watch

Founders Who Crushed It

Bald VCs in NYC You Should Pitch

When you're on the list, you're tweeting the heck out of it, very modestly of course, and getting all your investors in friends to do the same.  When you're not on it, you tell yourself the list was bullshit for whatever reason, or that you don't have time to pitch yourself because you're too busy running a real company.  

Unfortunately, these lists do matter and when you're not on them, you're missing out on opportunities for press that can cascade over time.  For one, journalists often use existing lists as the basis for other lists.  Also, when event organizers are thinking about speakers, lists of founders and companies represent easy references for invites.  Later stage investors would also be lying if Continue reading "You Want on That List and Here’s How"