Not All Money Is Created Equal

Screen Shot 2017-03-28 at 1.53.22 PMOK so if you’re pitching me and you’re not sure you want to take VC money, what exactly are you doing?! I’ve had a enough similar meetings with founders I think its time for a blog post on the subject.

Here’s how the conversation goes…”I made some money in my last gig/startup/whatever. I self-funded this project.” It’s going well but I’ve burned through my capital. One of my early investors is an investment banker. He says he knows other wealthy guys and we don’t have to go the VC route, give up board seats, deal with their firm’s baggage and listen to their myriad opinions.” OK that’s a bad start to a meeting with someone who is a gateway drug to more traditional venture funding. In many cases, it is also a bad way start to a tech company. Do your research and figure out what kind of money you want and need.

Funding from experienced early stage investors offers very valuable things beyond capital:

  • There is an established, milestone-based template for your development that you can follow which enables you as founder to focus on building a (profitable… well, eventually profitable) product your customers love.
  • There is a very organized — if sometimes opaque — marketplace for capital. With a little time and effort you can develop a long list of potential high-fit investors who cover your category, don’t have conflicts and have a good track record of success. And these investors are used to looking at deals, are comfortable with the lightweight due diligence possible at the seed stage and know the typical deal terms. Plus they can help you on future rounds of funding. I’ve directly introduced almost $100M in growth capital (other peoples’ money) into my portfolio companies over the years. Start on AngelList.
  • Speaking of deal terms, VC type investors know the difference between a priced round, a SAFE agreement or a straight up convertible note. They’re not going to come up with exotic funding agreements that turn off future investors. Good ones will be sure you’re set up for success in the next funding round.
  • Good seed stage investors have experience helping companies get to the next important milestone…which is product-market fit and the all important Series A. And let’s be honest, how many companies do you know that leave the seed stage so profitable with such great growth that they don’t need additional funding?!
  • And a great seed stage investor can become an excellent board member when you do your Series A. I’ve been a board member in about 25% of my deals over the years. A seed stage investor as board member has a couple of valuable attributes: they’ve grown with the founder and are a known quantity; they have different motivations and drivers than a typical multi-partner VC firm; often times they have operating experience.

I’m a contrarian in many areas but not in funding. I think companies should innovate in product, not financing. I’ve seen some big problems when founders take money from inexperienced investors:

  • “My early investor wrote a big check but has some pretty aggressive terms if I’m not successful.”
  • “My early investor introduced me to his rich real estate friends and they all want to write checks but I can’t get anyone to agree to deal terms. I don’t think I can get this thing closed and now I’m hosed.”
  • “My early investor wrote a big check but wanted a controlling interest in the company which seemed OK at the time.”
  • “My early investor was a father/son combo. The father was experienced in business but got busy doing other things and the son has no interest in helping us grow. In fact, he wants the money back for other things that he thinks are cool(er) — like a Lamborghini.”  (No joke)
  • “My early investor is pushing me for an immediate exit because he wants a return and wants to deploy the capital in other places.”

Who needs this freak show? Find good, experienced, balanced, helpful seed investors who know what they’re doing.

Investor Updates. Why Bother?!

Screen Shot 2017-03-28 at 1.43.23 PMInvestor updates – especially in the early days – are a must yet founders often neglect to do them. Why and when should founders do them?

Before the Series A, companies usually don’t have boards so there is no formal mechanism for reporting. Early investors are believers who understand the founder is super busy building her/his company. Many don’t demand regular progress updates. But it behooves the founder to build the discipline of regular reporting. I think a good discipline is to do a quick monthly update (a good, solid email is fine) for the first 12 months then move to more structured reporting quarterly. Why? It’s good practice and it’s an insurance policy.   I heard a phrase recently that I like — “Practice like you play” meaning if you’re practicing a sport or musical instrument or whatever, it’s likely you’ll play like you practice. So give practice your all. And I think building early reporting discipline will get you in good shape to do it once you raise your Series A and have specific reporting expectations. Plus – if you’re like many companies – you’ll be going back to the same early investors asking for a tweener investment before you get to your full blown Series A. And if the investor hasn’t heard from you since they wrote the first check — and the news isn’t totally rosy — they’re going to be less inclined to write another check.

Most of my portfolio companies suck at reporting. Truly. Some, however, are awesome. In the early days of Twitter, Biz Stone wrote a wonderful Sunday night note to the company about everything that happened that week and he forwarded it to the early investors. It wasn’t an investor update per se and wasn’t so much about metrics and milestones but it was a beautiful and heartfelt insight into what goes into building a great mission-driven company. It featured stories about people in the company and how users were using Twitter in mind-bending ways. Biz should turn those early notes into a book. Jason Goldberg also did terrific updates in the early days of Fab. In fact, I’d say he was radically transparent.  Among all my portfolio companies, the best at early reporting has been SellBrite. Brian, the founder, writes a regular, detailed report about the business. No hyperbole. Just fact and insight. It’s a pleasure to read, not just because the charts are all up and to the right (which they are), but because it gives a very good overview of how things are going…hits and misses…kpis…milestones…what’s keeping the team up at night…everything you need to know to understand the health of the business. At the end of the post, I’ll share an outline of what the best updates include.

I can usually gauge the health of the company from founder communications. In all cases, if a founder is good at sharing wins and keeping investors up to date in some fashion and then goes silent it’s never because the company is crushing it. One of my companies was on a great trajectory for months and months then went silent. In the back of my mind I thought hmmm something’s up. I finally got around to writing the founder and sure enough they’d hit a big speed bump. I think in those situations, the instinct is to hunker down and focus on the problem. But I think that instinct is absolutely wrong. I think the right thing to do is be open and engage your investors. There is a high likelihood one of your investors has seen this movie before and might have valuable insight.  It was the same story for another one of my companies…everything was going well…updates were terrific then…crickets. After a few months of silence, I got a panicked note that the founder needed a bridge because cash was short. Ultimately I contributed to that bridge but it took a while for me to reconnect with the company and founder and frankly it left me feeling a little squeamish. You have a bond with your early investors. Keep that bond. You might need it.

So if you’re a founder and it’s early days you know what to do. WRITE THOSE UPDATES. Once you get to a Series A or B (and other peoples money) you can be more casual with early investors. Post Series A, if I haven’t heard from a founder, I’ll do periodic check ins. “Hey, how are things going…” And I’ll often re-engage around fundraising. I have a good network and have helped founders with introductions that have produced almost $100M in checks.

Now, a few words for investors. I’ve seen investors who are absolute jerks. They write a small check and feel like they own the company. They hit “reply all” to every update email and panic at every hiccup, offering advice on every little thing. OMG shut up!  If you want to opine, make sure the topic is material and your input is worthy. The worst is when you see a note that says something like “my niece used this app and shared it with her friends. They all said they don’t get it. You need to do XYZ.” Who knows if the niece is even the target market. The founder has much better sources of insight data. So now you see why founders shy away from updates. In cases like this, I’ll usually have a quiet and polite conversation with the investor about what’s reasonable. It usually starts with “Dude you need to chill out!”

What’s in a great update:

  • KPIs (every category has it’s unique metrics, e.g., MRR for SAAS, GMV and liquidity for marketplaces)…Share the numbers and context.
  • Hits/Misses i.e., Good/Bad…here’s where you can share whats working and what’s not…and ask for help if you need it.
    • How you’re progressing on the product roadmap
    • How you’re doing on customer acquisition, CAC trends, etc.
    • What you’re doing in BizDev.  What’s working and what’s not
    • How the team is coming together, key positions you’re hiring for
  • Cash On Hand and Burn Rate
  • Help Needed From Investors (fundraising, hiring, BizDev intros, etc.)

Pitch Me Something Fanfuckingtastic


Even though I’m a seed investor, I look at a potential investment with the eyes of a Series A investor:

  1. Team: Amazing, passionate, articulate, experienced, connected founding team with strong product, tech, business and growth experience and a track record of success, united by a compelling vision, mission and purpose.
  2. Product Market Fit: Product that has product/market fit, great traction, is growing at a very nice clip, has super happy customers with a positive Net Promoter score.
  3. Model: A killer market and model. Massive potential market. A repeatable business that can scale. Network effect properties where more is more for all. A natural moat that deters competitors. A sound business model with great unit economics.

This takes a lot of imagination and creativity on my part because no seed stage deal *ever* looks like this.

Companies are messy in the early stages. Teams, products and models are most often incomplete. I’m looking for something in each of the three areas — some part of the story that is…well…Fanfuckingtastic. And there are some non-negotiables.

Team: The earlier the company, the smaller the team so getting all those boxes checked is very rare. The most important thing is that the founder’s core strength is the secret sauce of the company. Jordan was the only full-time team member at Sktchy when I invested but had a truly awesome designer and developer helping out (part time). Jordan is a terrific community builder. It’s in his blood. It’s what he talks about when he talks about Sktchy. And that’s the secret sauce of the company. The founder has to be Fanfuckingtastic. At something. Period. Non-negotiable.

Product and Product Market Fit: Here is where imagination is required. Usually the further along the product is, the higher the valuation. I need to see a product with *some* consumer feedback. When I invested in OfferUp, the app had been launched in Seattle and there were something like 3,000 listings. Did they have $1M in monthly GMV and at least 10%+ liquidity (things Series A investors might look for in a marketplace)? Uh, no…just 3,000 listings in one city. Back in 2011 when Nick and Arean launched OfferUp the only way to sell your stuff was on Craiglist or Ebay and neither had mobile apps that made it 1-2-3 easy to photograph, list and sell your used baby stroller. OfferUp did just that. It leveraged all the new tech that made smartphones powerful computing devices (camera, geolocation, etc.) to make it super easy to sell. Users loved it.  It didn’t take too much imagination to see the potential right away.

Model: If imagination is needed for product and product market fit, then clairvoyance is often needed to see the business model. In the case of OfferUp, I didn’t have to do much market analysis to see a massive market, the potential for network effects and a great business model with terrific unit economics. It was easy to imagine a scenario where the boxes could be checked by Series A. And, indeed, they were. In the case of TheRealReal, this required more imagination. Julie had a great team when I invested. She had a great product with clear product market fit. Although she had a fast-growing business already, I had to do a bit of work to convince myself that a) affluent people would actually take the time to consign their merchandise, b) there were enough of them to provide the supply required to build a $1B company. I got there in about 24 hours and very quickly TheRealReal proved points A and B to the world. In the case of Twitter, it took clairvoyance. The app had just launched. There had never been anything like it. 140 characters to communicate a thought, idea or update? Via phone? It was abundantly clear the world was going mobile. I could just imagine 1,000 ways Twitter could be used by people, brands, press. I could just see the power of the status update. So tangible. So real.  I’m glad I wrote that check.

When you pitch, you don’t have to check every box.  But you do have to show me something Fanfuckingtastic.

Talking numbers or why valuation REALLY matters

Screen Shot 2017-03-28 at 9.20.16 AMIt’s time for my semi-annual blog post haha. I want to write more frequently, I really do. But I get caught up listening to pitches and whatever I’m helping a company with and it goes by the wayside. Excuses. Excuses. I know.

Valuation has been a big topic in recent years and two years after the mythical bubble was forecast to burst I have a few thoughts to share.

I’ve passed on a larger than normal number of companies recently over valuation. And that’s odd because we’re past the crazy frothy period of 2015. I don’t nit-pick over valuations typically and I’m not one to micro-optimize terms. I’m looking for fair deals that motivate the entrepreneur and come with a nice and clean cap table and vanilla terms so we have no objections when raising money in subsequent rounds. Pretty straight-forward stuff.

That’s why I’m disappointed when founders come forward with absurd, crazy, eye-popping seed-stage valuations. Why don’t I pay up and shut up? Well, beyond the very obvious fact that high early valuations affect future returns, they also set up a very high hurdle the company has to cross before raising a follow on round at a commensurately higher valuation. They create unnecessary execution risk and can lead to Hail Mary behaviors.

Last year an interesting company came to me (pre-product, pre-revenue, interesting team but they weren’t 3x entrepreneurs with decacorn exits – just good, solid entrepreneurs). I liked the concept. I liked the space. I liked the team. All good. But the valuation was breathtaking…and we’re not talking AI or another flavor-of-the-month here. Wow. I told the founders the valuation was extraordinarily high but I’d love to hear what they thought justified it. I was prepared for some hustle and a good back-and-forth about their genius business model or the secret sauce in their brilliant algorithm or the insurmountable moat their technology ensured or how they crushed it in user tests. Instead the answer was “We’re a San Francisco company so we feel we deserve this valuation.” Pick me up off the floor. That was such a deflating answer.   No hustle. No insight. No passion or conviction. Just entitlement. Needless to say I didn’t write a check. Yikes.

I found another great company recently that ended in a #fail for a different reason. I loved the founder. Super high hustle. Smart. Scrappy. Great UX chops. All the things I like. The product is brilliant. It is. But there was no customer feedback as of yet so it’s a big bet. But I was willing to take the gamble until the conversation about valuation.   The number was big. I gulped and asked nicely why he felt it was justified. The answer I got? “Well we raised our friends and family round at a very high valuation of X and only gave away a small amount of equity. So we need the valuation to be Y because we don’t want to disappoint our early investors. Plus we have a lot of interest.” ARGH. Friends and family are not usually valuation sensitive. Many probably don’t know what’s reasonable. They’re investing because they believe in you. But don’t take advantage of that and command an absurd valuation to minimize your dilution. One of two things will happen: you’ll have to go back to them and explain you’re doing a “down round” or you’ll face the risk of not being able to raise money because you’re trying to get the valuation up.   If you are able to defy the odds and raise a nice up-round then you’ve set yourself a BIG hurdle for the next fund raise. You’re going to have to have a super duper home run to get there. And that could lead you to do ill-conceived Hail Marys. I’ve seen that movie and have never liked the ending. See above. Read Good to Great. Be sensible. Take it step-by-step. Yes, reach for the stars, but climb a ladder to get to them.

I had a third #Fail around a cap table. The founder launched his app and it took off like a rocket. Totally broke, out of desperation, he took a very small check that felt huge at the time but gave up an enormous slug of the company to get it. That’s just a terrible burden to carry forward. In a situation like that, I could get actively involved, meet with the initial investor and try to work out something that’s a #WIN for all while not polluting the cap table but that’s a big expenditure of time.

So founders, please think sensibly about initial valuations. I know this sounds self-serving but I think it serves your interests best. Oh and if you are going to go big, then have a fantastic story (product, IP, traction – SOMETHING!) to back it up.

Two More in Miami!


It’s been a busy Q4 in sunny SoFla!  I invested in two new Miami-based startups and tripled-down on an existing investment.  I think of myself of a contrarian in that I make picks others don’t.  With these two picks I contradicted my own investment philosophies (no MarTech,  no Media).  Go figure! solves a big problem I see in my portfolio companies.  And that’s growth through referrals. — which did this brilliantly — saw huge growth from friends referring friends.  I was fiendish about racking up referral wins on  I wish Jason had productized his toolset.  Why are referrals a problem?  Developing a great refer-a-friend program with clear attribution, easy but detailed metrics and flexible campaign-building tools is a lot of work developers simply don’t want to do or don’t have time to do.  Too many growth hackers hit this wall and opt to do Facebook or Google ads instead because its easier.   Alex Nucci, the founder, learned all about this in his growth hacking job ClutchPrep and set out to build tools that make it easy to develop and manage word-of-mouth marketing programs.  During the pitch, Alex told me his story and showed me what he’s built so far. I was impressed.  But I couldn’t get there.  SAAS is tough.  MarTech SAAS is even tougher and I’ve been avoiding MarTech for awhile.  Plus Ambassador is a well-funded competitor.  So how did Alex get me to write a check?  He showed me how scrappy and hungry he is by doing a very detailed referral program assessment of one of my portfolio companies.  He went through every touchpoint that could be used to increase referrals and described how the company could do better at each point.  It was a fantastic piece of work and it showed me how Alex gets his hands dirty tearing apart the UX to really understand where the impact points are.  It also showed me he has that magic and rare trait called initiative.  His assessment could be the basis for a very effective consultative selling approach.  He got me “there” and I wrote a check.  I’m in!  A big thanks to Shawn Convery for the intro.

WhereBy.Us  builds experiential media for the world’s curious locals. Huh?!  WhereBy.Us puts an email (yes email!) in your inbox, daily, with great local news — what to do, what to don’t, where to eat.  They encourage readers to “live like you live here.”  If you live in Miami and you’re reading this, you’re probably a millennial, one of their 30K subs here and you know the company as TheNewTropic. You’ve come to rely on it for great stories like Nine Tips For Surviving The Art Basel Traffic Nightmare.  They just raised a round to fund their expansion.  Their newest market is Seattle where they launched TheEverGrey with a coloring book.  The team is building local brands you just love and because you love them, advertisers love them.  When I think of WhereBy.Us I think of Refinery29 (I’m an investor) and Thrillist (I wish I was an investor) — both properties that have a unique voice demonstrating a very tangible “feel” for their readers’ needs/desires.  While I’m a big fan now it took me a while to get there.  Media is hard.  And Local is really hard so I had to hear the pitch three times before I got there.  Chris, thanks for your patience! And a big thanks to AGP for the initial introduction !



Introducing SKTCHY — my first investment in a Miami company!

Screen Shot 2014-09-03 at 10.23.57 AM

Shortly after I arrived in Miami, Wifredo Fernandez — one of the founders of TheLab Miami (the coworking space I work out of) — introduced me to Jordan Melnick.  Jordan’s a native Miamian, a blogger and journalist, a regular around Wynwood and now a purveyor of inspiration.  He and his team created an app called SKTCHY.  I think of it as instagram for artists but it’s actually much more/different than that. You can post photos of yourself on Sktchy to inspire artists to draw you, paint you, maybe even sculpt you. And of course you’re welcome to choose someone else’s photo to draw yourself. There are no drawing tools in the app. The Sktchy team decided to leave the creating up to the experts — the artists — and instead focus on becoming an ever-growing source of inspiration and a place for them to share their creativity with the world. The community enjoys the artwork with wows. Relationships form.  It’s the give-to-get principle in action. Inspire me and I’ll do a portrait.  The concept and indeed the UX is simple, arresting, engaging.  I saw it and loved it.  Why? I believe there is an underserved market here. More on this in a bit. Jordan and team did a great job with the UX, they’ve got some early traction and there is very good engagement among users.  It’s an early bet because I’m the first investor but I feel great about Jordan and the team and love the app.

In doing my due diligence, I was looking for a sizable market and good, early engagement and I found both.

Way back in the days when MySpace was still something and FB was opening up the platform, I came to believe social networks would go vertical and niche.  In fact, I wrote two ClickZ articles on the topic in 2006 and 2007. [I am afraid to re-read them but you can here and here.  No ridicule please — I wrote those almost 8 years ago!]  Fast forward several years, and under that thesis I invested in a gay social network called (which later pivoted to become  Today there is an endless array of niche and or vertical social networks. In looking at SKTCHY I recalled Richard Florida’s controversial thesis about the rise of the creative class.  In 2002 Florida said that there were 40 million workers in the US engaged in the creative class.  The figure stuck with me.  You don’t have to walk around the Mission in SF, Wynwood in Miami, or Williamsburg in Brooklyn to see members of the creative class at work.  They’re in every town.  In the US alone, you have more than 1.5 million professional artists, architects and designers (very narrowly and traditionally defined) and many more who create beautiful things. Using the 1:10 to 1:20 ratio of content creation to content consumption, you can extrapolate yourself to an audience in the US that is easily in the tens of millions.  If you extend that worldwide, you can see a potential audience in the hundreds of millions. Oh, and remember DrawSomething?  It was downloaded 50 million times before Zynga finally bought it.  OK, that’s not a great analogy…but you have to admit it was a phenomenon!

The early engagement on SKTCHY is very good.  The app has been downloaded nearly 90K times.  There are 30,000 original artworks in the archive from artists in 60+ countries and 1,000 or more are being posted every week.  In the last week, there have been 25K “wows.”  A popular work can get 300+ likes.  People are creating and interacting with the content.  

And user feedback is superb:

“Not including my “free draws” or works in progress, this is my 100th Sktchy-inspired portrait!  Thanks again to Jordan and the entire Sktchy staff and community for not only an amazing app, but a seriously life-changing experience… I am so grateful for all of you.  This has been hands down the most productive year I’ve had art-wise in my entire life… And it’s not even over yet!  Thank you!!”  Artist: Krystal Figueroa


“I didn’t even know I could draw until I downloaded this app”  I didn’t draw AT ALL!  But I felt bad people drawing me and me not returning the favour and now I have almost 100 people tagging me to draw them and a couple of people on Facebook want to commission me!  Me?!  My silly little doodles!!! X”  Artist:  Doodle Swan

What’s next?  A better on-boarding experience.  Easier sharing.  Faster load times.  Richer analytics.  And a few things the team is keeping under wraps.

Download SKTCHY, post an inspirational photo and enjoy some art.  You’ll get hooked like I did.   

Outsider Art, Edmonton and Granify


Half my deals come via referrals from people I know and trust — mentors, fellow angels, former employees, etc. (e.g., Say:Media, 140Proof, Thank you friends! The other half are deals I find on my own — companies whose products I love and/or entrepreneurs I admire (e.g., Twitter, TheRealReal, MommyCoach)

I’ve gotten to know Giordano Contestabile (@giordanobc) because we’re both early investors in TheRealReal.  We both made very early bets that Julie Wainwright would build the world’s premier online consignment shop and that’s precisely what she’s doing!  SHE IS KILLING IT!  You’ll hear a lot more about TheRealReal in the coming months because Julie is building a break-out company — a unicorn in the making.  Really!

Back to Granify.  In September, @giordanobc introduced me Jeff Lawrence, the CEO of Granify.  Jeff and team are building what I believe will be an ecommerce powerhouse based on a simple mission: help online retailers make more money.  How?  Granify tracks your customers as they travel through your ecomm website, predicts whether or not they’ll buy and if they’re predicted not to buy, understands why, then presents them exactly the right message at exactly the right time.  And BOOM! they convert.  SWEET!  If you talk to any ecomm CEO, she/he’ll say their biggest headache and their biggest leverage point is on-site conversion. #TRUTH

Jeff and I chatted.  I was impressed. I like simple solutions to complex problems.  I like that their dashboard tells you exactly how much you’re making from their service.  I like that they only make money if you make money.  I like companies that productize rather than servicize solutions. The ecomm space is massive.  

BUT Jeff was in Edmonton (that’s in Alberta, Canada —  just a quick 4 hour and 12 minute flight from NYC) and I couldn’t break away to buzz up there and meet him.  It’s also fiendishly COLD in Edmonton (it’s the northernmost city in North America with a population over one million, according to Wikipedia) and I’m a warm weather friend.  (Today Edmonton will reach a high of 10).  Initially, I was concerned that the company was in a relatively remote location. But then I thought about Omniture.  A billion dollar exit.  Built in Utah, not Silicon Valley.  OK.  I started thinking remote might be good — if it’s cold, people stay indoors to write code and mine data. Hackathons and investor pitch contests are not an everyday distraction. OK I’m warming up.  Granify kept coming up.  I had lunch with another NY angel, Jerry Neumann @ganeumann who worked for the private equity firm that took Organic private back in the early 00s when I was the CEO.  He could have been a d*&k back in the day but wasn’t.  In fact, he was — and is — a super nice guy.  It turns out that Jerry is also an investor in Granify.  I figured it was worth another look.  Jeff made a trip to NYC.  His story was even more convincing in person and he closed me on the spot.  Yay!

I’m an art lover and like many NYers I make the rounds to the big shows when they swing through town.  I particularly enjoy the Outsider Art show.  The work is fresh, dynamic, unaffected and unfiltered.  If you like art porn, check out Eugene Andolsek — a true savant (see photo above).  I have a few of his works.  As an investor I’m a bit of a contrarian and certainly an outsider.  I don’t do the cool kid deals because I’m not a cool kid (I never was).  Just sayin’.  

Three of my recent deals are “outsider deals.”  They’re outside the Silicon Valley/Alley bubble.  OfferUp is in Seattle.  Snapwire is in Santa Barbara.  Granify is in Edmonton.  I see a pattern here.  

What do you think?  Do you shy away from OOT deals?  Or seek them out?