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This is going to be BIG...

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

Mon, 23 Apr 2018 12:10:20 +0000

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... scrolling="no" allowfullscreen="" src="//" width="640" frameborder="0" height="480"> 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: scrolling="no" allowfullscreen="" src="//" width="854" frameborder="0" height="480"> 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 curr[...]

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

Mon, 16 Apr 2018 11:54:47 +0000

"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 [...]

You're the CEO.

Mon, 09 Apr 2018 11:30:00 +0000

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.&n[...]

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

Mon, 26 Mar 2018 14:38:51 +0000

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 parents returning to the workplace to work flexible schedules, etc.  

Creating legislation around this creates move problems than it solves.  Plenty of perfectly healthy work environments occasionally dip into "off hours" time.  Maybe I've decided to work late because I took the day off tomorrow, but I need some bit of information from a colleague.  Maybe that person is difficult to work with generally, and is on the verge of getting fired.  A nice colleague might respond to my "Hey, what revenues were you projecting this year?" text with a quick response, but this person just ignores it.  Now I can't do my job because he doesn't feel like doing his.

After generally mistreating other employees, when they finally fire him, now he uses this law as his cover--and the company is potentially going to get fined.  

White collar workers connected by e-mail are quite capable of maintaining the proper balance here through clear communication of expectations.  This is why work hours aren't defined--because if I say 9-5, the person who likes working 10-6 is going to be less productive.  When you create a rule for everything, you lose efficiency.  When do work hours end?  5? 6? 7?  What about the day before a big client presentation?  What about when your co-workers are doing a presentation in SF and it's 7:30PM here?  They're working, but you're "off?"  They need the latest copy of the deck and they're trying to reach you, but you just sit there with your arms crossed because you're "off the clock?"  Is a sales pitch an "emergency?"  

Good luck enforcing this.

Trying to litigate what constitutes an "emergency" e-mail is foolhardy and isn't worth the government's time, not to mention that these mobile technologies actually allow people to be better at work life balance in many cases.  Do you need to be checking e-mail 24/7?  No.  Would it be helpful to respond to something after you've put the kids to bed, so that your earlybird co-worker has what they need on their 6am train ride into the city?  Yeah.  And if you're on your phone tweeting cat pictures, your co-worker has every right to get annoyed that you couldn't get them a quick answer on that memo if they're paying you over $100k/year.  

If you really want to go after abuse of workers, check out all the delivery employees who bring your lunch by bike without Worker's Comp insurance and without any Fair Work Week protections, because they're all 1099 employees.  


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

Mon, 19 Mar 2018 12:00:02 +0000

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 be like, "I don't know, what were you thinking?"  He doesn't know anything about startups and you're lucky he even thought of you at all.  You're going to now throw it back to him to plan out what he might do for you?  No, you have to make an ask.Second, anything you come up with is barely going to register for him in terms of level of impact, but it's going to be more then game changing for you--it's going to feel ridiculous.Maybe your company is seed funded, or has some friends and family, or is barely more than a Powerpoint.  Even if you have your Series A, the scale that you're operating on probably doesn't even come close to what he's been thinking about these days.  He's on the "ending malaria/making sure every woman in the world gets equal pay" kind of level", and you're out there building an app with three devs, some cheese dip and an office dog.  Even if you have a worthwhile mission, you're going to have to get over the fact that anything that he could come up with that he'd pay attention to is going to feel crazy to even ask of him. But this is how you make a leap as a startup.  One of the easiest things you can ask of something like that is to invest.  Investing insures that someone is always part of your company.  It gives you an excuse to e-mail them and your updates keep you top of mind for them.  It gives you an excuse to ask for more later.  Getting someone to invest in your next round is like getting to wish for more wishes and having it granted.Get over whether you know if this person invests or not or what size check they can write.  Any person who gets to this level of success could probably write at least a $10k check or maybe more than you think.  Remember that you're not asking for their money--you're providing them with a great opportunity for them to trade their wealth for interestingness.  This is something they do all the time in a variety of ways.  Advisory boards are also a great way to rope people in that you probably have no business getting on boards.  The key is to make them about something bigger than just your company.  If you're a financial startup, make them about financial empowerment.  If you're a fashion company, make it about style trends.  If you're a consumer product, make it about world class customer experience, etc.  It's really easy to be focused on short term goals as a founder--getting to that next raise, making that next hire, or just making sure your bills are paid.  The companies that make huge leaps in impact and value execute these kinds of headline making moves, leaving their competition far behind in the rear view mirror.  Knowing what these moves could even be is hard, and it's probably something worth talking to your investors or thought partners about, and definitely something to plan around.  This comes into play so many times.  People you know will say, "Hey, I know the former CEO of X and she's retiring and looking for something to do."  Don't let those opportunities pass you by.[...]

Find Success by Helping a Mom Find Success in Your Company

Mon, 12 Mar 2018 12:40:49 +0000

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 everyone else, even though the results said otherwise.  Eventually, they let her go.  What struct me about this situation was that it was a culture that obviously couldn't scale past young, single people.  I thought, "Wow, there's no possible way anyone with a kid can ever work at this company."  As I spoke with Adam Milligan about in the Startup Recruiting Podcast, tech companies are idea factories--and they win by bringing the best ideas to light.  That means that successful environments are ones that foster a diversity of perspectives, support great communication, and favor quality of solutions over the speed and hours of simply "typing" the code.That's why a great barometer of your potential for success can be found in how ready your company is to support a mom (or a dad, of course) returning to the workforce after taking time off for family.  If your hiring process really does favor the people who can bring the best ideas to the table, statistically speaking you should have a lot of moms in that process, particularly when they're often your biggest customers.  The question is, can they find success in your environment, and what might hold them back.That's where efforts like Path Forward come into play.  Path Forward is a nonprofit organization on a mission to empower people to restart their careers after time spent focused on caregiving--not just moms raising a kid, but all sorts of family situations. They fulfill this mission by working with companies to create midcareer internships — sometimes called “returnships” — to give women (and men) a jump start back to the paid workforce.I interviewed Path Forward's founder, Tami Forman, on the Startup Recruiting Podcast (or here at Soundcloud, in case iTunes hasn't updated yet) to talk about companies can go about making their environments supportive of this transition and how the companies involved in the program have tapped this underutilized talent pool.  (Over 80% of the participants in their program wind up getting hired by the companies that they intern at.)I'm a big believer that companies should rethink their purpose in order to achieve sustainable success.  What if the goal wasn't to create shareholder value, but to create the best place for the most talented team (not just individual people) to work?  Remember, teams are more than the sum of their parts.  Wouldn't product and sales success flow naturally from that?  So why not focus on it as a priority?  Seems to me that's something that should be done from day one, not just when you get around to hiring your first Head of People.  [...]

What I Say When a Founder Asks for Feedback

Mon, 05 Mar 2018 05:49:43 +0000

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

Thu, 01 Mar 2018 18:14:57 +0000

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... mozallowfullscreen="" allowfullscreen="" src="" width="640" webkitallowfullscreen="" frameborder="0" title="The Financial Gym" height="360">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 savings.  Seven 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 decade.  And wages?  Wages have grown 0.2% annually since the 1970's, lagging inflation.  Each new generation is forced to do more, with less, despite startlingly low levels of financial literacy--only a quarter of millennials can demonstrate a basic understanding of personal financial concepts.  People are graduating with sky high expectations of themselves and what they can do in the world, but no one ever bothered to teach them how to manage a shrinking checking account in a world of low pay, suffocating debt and high costs.  Apps might work for the most disciplined and well off people--but the moment you have to make hard decisions about selling things to downsize, when you want to talk about a purchase, or when you need some extra accountability to stay on track you'll fall right off of them.  Anyone who has ever had a personal trainer give you a 6AM wake up call or who has gotten grief for missing your regular Soul Cycle class knows you can't cheat a human coach.  Membership provides you planning meetings, follow ups, regular check-ins, as well as events at their beautiful new space in Flatiron (with more locations to come, obviously!).  There's no downside to scheduling a free 15 minute warm-up call to learn more.  What I also want to add into this story is a little bit about expectations.  I don't think I've ever met a founder who has more expectations of themselves than Shannon.  Sure, we have a financial plan, but Shannon's got a whisper number of her own that she's managing to herself that I'm sure is an order of magnitude greater than the plan we set out.  Much of our interaction is around making sure not every move she makes at the Financial Gym is going to go right--even though she's proving me wrong so far.  :)  Her bio reads that she runs "the world’s greatest financial services company" and I honestly think it's true--or it will be when the Gym is in every city across the country.  I don't think there's a single company in the finance space whose customers have the same kind of positive emotion towards a company as members of The Financial Gym.  She also faced a ton of expectations during this fundraising.  Other investors wanted her to be anything other than what she was.  They told her to play down the brick and mortar in her pitch.  They said she should be an app.  They said she should be a bot.  People have asked me how I've come to fund 20 female founders and counting, and I think I realized after meeting with Shannon what gets in the way--expectations.  I can think of countless deals that I got to a yes only after asking the question, "What do you really need to raise?" or "Are these numbers really as far as you t[...]

The Atomic Element of Your Marketing

Mon, 26 Feb 2018 07:37:25 +0000

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 was an atomic element of our marketing.  What was it that we actually wanted our marketing to do or to show?  Do we inspire?  Do we tell stories?  Do we help?  Do we show off?  Are we all about people?

If we're about people, than people need to be in every single piece of marketing collateral that we create.  If we tell stories, than everything you see from us--from the TV ads to our packaging to our Instagram posts, will be stories, because that's what we do.  

Once you figure out your atomic element, it becomes a lot easier to fit your brand message into various channels, because you know the vessel of delivery--the atomic element of your marketing. 


How VC Fundraising Favors White Men

Mon, 22 Jan 2018 14:11:51 +0000

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 to walk the minefield of a white male VC opining on the topic.After backing a higher percentage (around 50%) of founders that would fall into various diversity categories and listening to a lot of people's perspectives, here's what I've come to believe about diversity and the fundraising environment--and I'm open to new perspectives on it.But first, a disclaimer:I'm a straight white guy and come with all of the requisite biases and privilege--and so while I cannot speak for anyone outside of this category, I'm attempting to provide a helpful perspective from the funding side of someone who is listening and actively backing diverse founders.  I've opened the comments on this one--because while I normally think comments are kind of a pain in the butt to manage and I'd much rather someone e-mail me if they really cared to have a conversation, I think it's important enough for this post to get into as much dialogue a possible.  I will not, however, tolerate hate in anyone's direction.Ok, now that those two things have been addressed, here's what I believe is true--and, more importantly, simultaneously true:1) Diverse founders face conscious and unconscious discrimination.2) Yet, the vast majority of investors would back anyone they thought could make them and their investors money.  Why they haven't is not an uncomplicated issue and does not have easy answers.3) The fundraising process favors white men.  4) The diverse background of the founder is not the main reason why most diverse founders get turned down for investment.5) Both diverse founders and investors need to change their behavior if the funding statistics are going to change.[Ducks head.]Ok, let's dive in... There is discrimination in the world.  This should surprise no one.  This was what one of the founders who wrote back to me last week sent.  On an app advertised to "meet inspiring people" for meaningful networking, someone tells this black founder, whose last name is "Youngblood" that is name is inappropriate.  Clearly he assumed that he was using some kind of username, and that it was a gang reference of some sort--like, "Young Blood" as in the bloods and the crips or something to that affect.   The person goes on to blame the uncommonness of the name.  Do you think he would have had the same reaction to former Major League Baseball utilityman Joel Youngblood?  I highly doubt it.  Diverse founders here that kind of idiocy all the time, and undoubtedly it's incredibly discouraging.  Investors need to give some serious thought to what comes out of their mouth before speaking if they're going to make any i[...]

The Scariest Thing About Working at a Growing Startup

Wed, 10 Jan 2018 15:23:05 +0000

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 people who, on day one, can't do it as well as you've learned how to do it.

The same holds true for relationships.  Maybe you were interfacing with inventory buyers, or interviewing every candidate--but at some point, you have to hand over those relationships, too.  

If other people start doing your job and leveraging your contacts, what happens to that security?  What happens to your sense of identity in the organization?  

Every early startup employee faces this choice.  Do you dig in and play the territorial game, or do you step up to become an indispensable manager?

An indispensable manager not only builds teams, but recognizes a new level of professional responsibility.  You speak with the weight of the company behind you, so you need to make sure you're actually on the same page as the rest of the company.  As an individual contributor, you may not see the effects of not being on board with management decisions--but as a manager, people look up to you. 

Sometimes you just have to say your peace behind closed doors and then get on board for the good of building something bigger then yourself.  At the end of the day, you're not the founder or the CEO--and the decision you have is to stick around and row in the direction everyone else is rowing or jump ship.  

Successful startup execs build bridges and consensus.  They recognize that what the enable the company to accomplish is their track record more than the series of their own person accomplishments.  This means ceding credit to a team and abandoning the "I" for the "we".  You don't want to win every last argument--you want the company to win.  

This is an extremely difficult thing for the type of go-getters and hard workers that are often attracted to startups.  A great individual contributor isn't necessarily a great team builder--but that doesn't mean it can't be learned.  The keys are professional feedback and self-awareness.  Knowing the ways you get in your own way are key to not letting it keep your career down.  Taking both outside and inside feedback--from above and below--to heart is a good first step.  I generally assume that any criticism someone has of me is true, until I can as objectively prove to myself that it isn't, and I wrote about that a while back here.

Startupping ain't easy, and neither is developing as an employee into a manager and executive.



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

Mon, 08 Jan 2018 12:45:00 +0000

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 cents a cup, but how do you sell enough lemonade to go public??

5) Why is your product special?  This isn't that stupid competitive chart where you have all the checkboxes and no one else does.  I want to understand if there's a reason why all of the sudden this angle is possible, and why others aren't likely to have the same advantage you will.  

6) What are you going to do with this money--specifically, what are the GOALS for the round, not how long will it take to spend.  Anyone can spend a million bucks in a year.

If you think you could use some help formulating your pitch for an investor, and you might want to do some good in the process, I'm running a series of pitch workshops called "Fix Your Pitch for Good!" for charity.

Startups can sign up to go through an abridged 30 min VC meeting, and then we'll talk for 30 minutes about what could be improved, how to organize it better, and what VCs need to see.

And if you're just curious, you can just come watch.

For startups pitching, the donation is $250, which will be 100% disbursed to some charities I'm currently raising money for, like the Challenged Athletes Foundation, Team for Kids, and ScriptEd. For attendees, the suggested donation is $25.  



What Valuation Should I Expect in My Seed Round?

Mon, 01 Jan 2018 22:07:02 +0000

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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 somewhere in the middle, both feel a little regretful about where we wound up, and that's probably the right price.  :)


You Want on That List and Here's How

Tue, 26 Dec 2017 17:25:42 +0000

With each passing year, we get another set of lists:Startups to WatchFounders Who Crushed ItBald VCs in NYC You Should PitchWhen 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 they don't reach out to see what's up and why a company might be featured.So how do you get on one of these lists?  Simply put, you need to make yourself known to the people writing them!  But how?  Ok, well, here are some tips:1) First, figure out who we're talking about.  Make yourself a comprehensive list of who is covering your space.  Who has written about the five startups most like yours or most likely to get mentioned in the same conversations?  Who has written about the five companies most likely to acquire you?  What influencers are building a brand about being an expert in the space?  Are there any podcasts you'd make a great guest on and who runs those shows?  Who runs the conferences you'd make a great speaker at (like, literally, which person picks the speakers?)2) Reach out.  The best way to contact someone is when you're not asking for anything.  Offer yourself as a resource.  You're an expert on something, otherwise you wouldn't be starting a company around it, right?  Write to all these contacts and just say that you're available if they need a quote, some background info on the space, or they want to spitball trend pieces.  Perhaps you might offer them 3-5 interesting facts they could use in future pieces--the kinds of surprising stats you might have had in investor pitch decks that made you want to start this company in the first place.  3) Interact over time.  Follow all of these folks on social media.  You decided to build your career in this space and they're pushing out content about it.  You should have opinions, be able to ask questions, and certainly be willing to share their content if you're looking for them to eventually share what you're up to.  It's a lot better to have 3-5 different touch points with someone and then wind up in their inbox than to be a complete stranger.  The best way to do this, obviously, is to do this authentically.  These journalists and influencers are people, after all--and they do more than just follow Fintech or the On Demand Economy.  Maybe they run or cook or they follow the same college sports team that you do.  Find ways in which you can connect on a more personal level and stand out for them as a person they identify with instead of just as a founder looking to get a story placed.  4) Offer up your own lists.  Share your view of other founders who are doing awesome stuff or offer to make introductions.  You're obviously not going to be the only company on a watchlist so if you can help someone fill out the rest of the list, you're more likely to be included.  And if you hate what everyone else is doing in the space, you're likely to be obnoxious to talk to and probably won't end up on anyone's list.  Don't be a[...]

Five Lessons Learned from the Ample Hills $8 Million Raise

Thu, 21 Dec 2017 20:14:00 +0000

Board meetings at @amplehills are dangerous. A post shared by Charlie O'Donnell (@ceonyc) on Dec 20, 2017 at 8:06am PST When you're Ample Hills Creamery, the #1 rated ice cream shop in the country you can pretty much throw everything you've been told about fundraising out the window.  Nothing seems to apply--you're not a tech company, you bootstrapped your way to millions in revenues before taking on capital, and you sell mostly through brick and mortar.  Yet, the lessons learned from their $8mm round of funding announced this week are still widely applicable to every startup--particularly food startups and those in four walls retail that struggle through the traditional venture process.Here's what I think everyone involved learned in this process.1) Find backers who love you for what you are, even if you're a square peg.When Ample Hills first raised $4 million in 2015, people asked if it was a seed round.  Technically, that's what we called it, but it didn't seem entirely appropriate given that it had already been up and running for years and had millions in revenue.  When we raised that first round, we needed to figure out who was even open to the idea of backing an ice cream shop with national and global ambition.  We hosted meeting after meeting, stuffing as many investors in the room as we good in groups, invited via waves of mass e-mails to anyone I thought might be interested.  What we found is that while most of the people turned down the invite, most of the people who showed up invested.  Ample Hills wasn't a deal for everyone, but for those that were open to it, they loved the company.Did that seed make this round our Series A?  Would we pitch Series A players?  I pushed that we should just say what it is--an $8 million raise to grow the company.  Who cares what we called it?  In fact, I thought we should have named our rounds after ice cream flavors but that was quickly shot down by the lawyers.  The truth is, it doesn't matter--that you can very easily get caught up in positioning, but at the end of the day, an investor who really wants to invest is going to invest.  It's too easy to think that if you tilt the pitch just a little one way or the other, that's going to make the difference, but that's Monday morning quarterbacking.  Rounds aren't close--they either happen or they don't, and an investor on the fence is a pass.  Investors who want to be in will find a way to come in and will structure an economic deal that makes sense, no matter what they call it.2) When you stray from traditional tech investors, leave yourself twice as much time, because they're twice as unpredictable.  Tech VC is a pretty mature marketplace--the players are known, the process is established, and so while relationship building might take time, usually you can estimate how long a deal will take with some accuracy (besides, of course, that it takes longer than the founder wants). AH kicked off this raise based on some inbound conversations with high net worth individuals back in the first quarter of this year--over nine months ago.  These types of folks, who may or may not have family offices that they work with, range in difficulty to work with.  Sometimes, the person whose money it is could just say yes, and points to a person to make it happen.  Other times, they hand it off to a team that could take months to do their work.  You just don't know.In AH's case, ultimately, the person we started talking with didn't actually wind up participating, but still remains a valuable contact and potentially a key partner for the future.  Howev[...]

Don't Be Dismissive

Mon, 18 Dec 2017 11:44:45 +0000


Finding Community in NYC Tech Again

Mon, 11 Dec 2017 13:00:30 +0000

There's a thread going on Twitter about doing a BarCamp in NYC again.  I started with a tweet from Jeff Namnum about how he joined the tech community...Forever grateful to @tonybgoode @noneck @whitneyhess @ceonyc and others for making a Long Island guy feel welcome a hundred years ago at barcampNYC. Absolutely changed my trajectory.— Jeff Namnum (@namnum) December 8, 2017 It touched off a whole discussion about putting on a BarCamp here again--a collaborative, open "unconference" where people could come together to share and learn about a wide variety of topics.  We haven't done one in NYC in a while, but moreover it feels like the sense of a common community we used to have in the early days of the tech community has been replaced by scale and a lot of heads down work.  Where there used to be the same crews of people attending the NY Tech Meetup every month, there is now 5 tech oriented Meetups a night on specific things like cryptocurrencies, ecommerce conversion best practices, and Clojure.  Sure, it's great that NYC has scaled into the second largest tech community in the world, with layers upon layers of knowledge and experience, successful growing companies, etc., it feels a bit like we've lost a little something about how we used to convene in smaller, more consistent and intimate groups. I've been thinking about why this has happened and I can point to a few things:1) My peer group of twentyish somethings grew up a bit, became super successful, coupled up, procreated, moved out to Brooklyn, etc., and just doesn't have the social flexibility they once did.  Or, they just got a big fatigued with running around doing events they weren't getting paid for all the time.2) The larger companies outgrew the community.  Holiday season used to mean getting invites to holiday parties at companies like Squarespace and Foursquare.  Back then, they were in offices that were yet unfilled, and opening up to the community still meant a manageable number of people.  Today, their own companies are communities unto themselves--and marketing and recruiting has gotten a bit more mature than just e-mailing a lot of people to consume egg nog.  3) In some cases, it was a reflection of what was big at the time.  There were no better spokespeople for their own products than Dennis at Foursquare, David at Tumblr, Jacob at Vimeo, Kortina at Venmo, etc, etc...  Participating in the community was almost part of the job.  In today's NYC, you wouldn't market Warby, Datadog, MongoDB or Casper with photos from last night.  No one is coming up to you at a bar anymore trying to get you to try their social app (RIP Hot Potato.)4) Space doesn't seem to be as easy to come by these days.  Remember when Sun used to host events at 101 Park?  How many events did Jack open CRESA's doors for us?  These days, there's much more competition for space to hold events and a lot of the spaces have professionalized, charging because they're now in the business of space.  Whatever the case, it's hard to figure out where to tell someone to go in NYC's tech and startup community if they want to meet up with awesome people doing cool stuff.  You can't just swing by Tom and Jerry's anymore. That's one of my 2018 goals--is to help make NYC tech feel smaller again, and more connected.  I'm starting with building up some cohorts of new seed-funded companies.  Raising a first round of capital is as good a proxy for "Someone vouched for you and you're a legit founder doing cool stuff with actual resources to give it a shot.[...]

Rethinking Our Heroes

Mon, 20 Nov 2017 07:32:49 +0000

As I sat in the movie theater watching Justice League, I thought a lot about the idea of a hero in the context of 2017.  

Generally, we've thought of heroes as possessing some kind of special power--or larger than life.  We've confused the powerful and influential for people we should look up to.  Yet, as we've seen in the retelling of a lot of the comic book stories on screen, our heroes aren't always purely good, nor are they as good at being people as they are at being powerful.  

This year has seen a toppling of those heroes the likes of which we've never seen before--Hollywood Actors and Directors, Former Presidents, US Senators, Would Be Senators, Midas List VCs, and yes, Confederate Generals.  We're being forced to reckon with our ties to everyone from slave-owning forefathers to Bill Clinton.  

We look up to heroes because we see them exhibiting power over others--yet it's this power they often seen to struggle to control and use appropriately.

As 2017 winds down to a close in the next two months, perhaps we can all think about what kind of heroes we'd like to have in 2018.  As many heroes fell this year, many others found the heroes in themselves--taking to the streets in protest for the first time, sharing their stories of mistreatment, and taking the time to listen and learn about the struggles of others.  

What kind of hero do you want to be?  Will you risk speaking up on behalf of others when it isn't popular?  Will you be vulnerable?  Will you admit when you were wrong, and try to make up for when you fell short with people?

Not all of us have a cape.  Not all of us are rich.  

But we can all be heroes.  


The Foolproof Way to Tell if Your Employees Have Issues

Thu, 09 Nov 2017 15:02:25 +0000

CEOs, founders and managers are more worried than ever about issues in their organization that they might not be aware of.  We've seen a ton of stories come out recently around bad workplace environments, and business leaders know that for every really bad story, there are a thousand festering smaller issues that need to be gotten out in front of before they get worse.  That's why it's critical that they understand the one question that can fish out whether or not there are workplace issues lurking underneath the surface of their companies.Here's the question...  are you ready?You sure?Ok...Ask yourself, "Does my company have more than one human working in it?"If you answered "Yes" then your company surely has workplace conflict and issues.  There is a 100% chance that when two individual humans work together in the same place, things will come up.  It's perfectly natural, but it's also something they don't have good tools to work out on their own. Bringing up conflict is difficult.  First, a lot of people are embarrassed that they can't fix a situation on their own.  They might feel like they're making a big deal out of nothing, even though it's making them more and more unhappy each day.  Second, even when a company does have outlets, like manager reviews or HR staff members, these relationships can easily be perceived as conflicted.  Maybe you're not ready to talk to HR or the problem is with your direct boss, and you don't want to make the situation worse because you can't change your boss.  Whatever the reason, these issues most often manifest themselves in unexpected churn.  How many times is the first hint of employee unhappiness the day they give notice about leaving?At worst, these issues come out in headlines.  In so many of the worst stories we've seen this year, there was a moment where someone could have head something off before the issue grew.  That's why Brooklyn Bridge Ventures recently funded Bravely.  Bravely that offers conflict and communication coaching for employees navigating issues in the workplace.  Through Bravely’s application, employees can confidentially describe the issue they’re facing and schedule a phone consultation with a ‘Pro’, an expert coach or HR professional with deep experience in helping resolve conflict, structure effective communication plans, and develop skills for constructive work relationships.Every single company has issues.  Hopefully not all of them are as serious as the ones that make headlines, but 65% of performance problems are linked to strained personal relationships, which happens everywhere.  Effective communication among colleagues, even for the small stuff that a lot of people let go, yields a significant impact on workplace wellbeing. The secret sauce of Bravely is to help employees feel empowered--given them strategies and language toolsets to address acute issues right on the spot.  Bravely is that first step; that safe place for venting, getting advice and putting a game plan together when you are not yet ready or lack the confidence to approach your boss or HR business partner.I'm excited to work with Toby and Sarah, two experienced former startup pros, as well as my co-investors Primary Ventures, Trailmix, and Correlation. If your workplace has more than one human working in it, there is absolutely no reason why you shouldn't talk to Bravely now.[...]

Five Lessons to Learn from the Success of The Wing

Mon, 06 Nov 2017 12:27:00 +0000

Two years ago, Brooklyn Bridge Ventures became the largest seed investor in The Wing--a network of co-working and community spaces for women founded by Audrey Gelman and Lauren Kassan.  They recently opened their second location in Soho after raising an $8mm Series A from NEA earlier this year, and their 3rd and 4th will open in the next few months.  It's perhaps the most well executed company I've ever been involved with, and there are some key lessons to be taken from watching how they've become one of NYC's fastest growing rocket ships.1) Don't assume anything.What I said above isn't exactly true--I didn't really invest in "The Wing".  At the time, the company was a Powerpoint about a space called "Refresh"-- a four walls experience that was a lot more utilitarian than today's incarnation of The Wing.  What changed?  Well, instead of resting on the initial idea after a successful seed round, the founders surveyed their potential customer base to make sure the space had exactly what people wanted.  While there was interest in a women's space that had showers and a place to clean up between work and going out, among other amenities, there was a ton of interest and curiosity around who else might be at the space.  In fact, the desire to network and connect with other women in a safe and supportive space was so strong, it drove the brand in a more community centric direction.  Just because some investors put money into your idea doesn't mean you can't question it--even at its core.  2) Make big asks.The Wing raised a $2mm+ seed round on a Powerpoint and they made no bones about asking for a big Series A to launch three more locations.  The founders knew they had something special and desired to make it appropriately impactful, which could only be done with real capital.  It sent a strong signal to the investor community that they had national and global ambitions, more so than if they had asked for "just enough to break even" or a smaller round than they knew they could execute on.  This is something I see with too many non-male/non-white founders in general, and I often find myself asking, "Is this the right amount to raise?  What would you do with more?" Undercutting yourself on a raise is fixable, but it makes even me worry about whether or not you'll make the big asks the company needs down the road--for that NYT piece, for that hire that would be crazy to take that leap, etc.  3) MVP and great product aren't mutually exclusive.  The original Wing location is smaller than their new spaces--but it's a beautiful, extremely well done and expertly designed space.  It served as an example of what could be done when you create such a community space, but it was built on a reasonable budget and less space than what future locations would entail.  Too many products cut experience and design instead of cutting features, making the limited number of data points users and investors have about your MVP that you can't build something interesting.  The Wing showed that they could build a great product, even if a little smaller, without breaking the bank, but also without scrimping on who they worked with around the design and the brand either.  4) Build a network ahead of building a company.When I first got the pitch deck, I had no shortage of people telling me that Audrey Gelman was a rock star and that I had to meet her.  That stood out more than anything she could have put into a deck.  Having that kind of network an[...]