9 Things Noah (The Biblical One) Can Teach Entrepreneurs

On Saturday, October 25, Jews around the world (or at least those who actually go to services) heard the story of Noah’s Ark. And so, with apologies to every rabbi who ever tried to teach me anything, here are a few things that Noah can teach entrepreneurs:

  1. Plan ahead. Noah didn’t wait until it started raining.
  2. Be different. The big winners are the ones who zig when everyone else zags.
  3. Go big or go home. Would a row boat have cut it?
  4. When you find the right mentor, listen carefully.
  5. Expect critics. I’m sure Noah’s neighbors had a good laugh at his little hobby. (“Hey funny guys, how long can you tread water?”)
  6. Build a diverse team. That said, you can probably get away with fewer than two of everything.
  7. Speed isn’t everything. In the ark, the cheetahs bunked with the sloths.
  8. Bad times can be good for survivors. Be the low cost producer in a price war, or stay lean when others are splurging and you can be the last man standing in an open field.
  9. Timing matters – don’t miss the boat!

Angel Investing – Fools Rush In Where Family Offices Dare To Tread (1)

Note: This post originally appeared as an article on FOCAPNET.FOCAPNET logo

 

Angel investing is hot… and not just because it’s so cool.

When for over a decade single-digit Venture Capital returns qualify as “top quartile”, seed stage investments have generated 27% ROI. (2)  So it is only natural that family offices and high net worth individuals are eager to get exposure to this sector.  The only problem is, they often don’t have the experience they need to do it right.

Here’s a typical family office startup story:

  1. A family office decides it wants to get into angel investing.
  2. One of the investment professionals goes to a few meetups and generally gets the word out that he is in the market for interesting startups.
  3. He starts getting pitched (directly, via LinkedIn, etc.) by a host of “investment advisors” representing “hot startups”.
  4. A few of these startups look pretty good so the family office invests.
  5. These investments fail miserably.
  6. The family office decides that startups are a “bad investment” and goes back to what it was investing in previously.

Hint: Step 3 is where things ran off the rails.  I’ll get back to that in a moment. 

 

Why family offices are ill-equipped for angel investing

The more sophisticated family offices employ investment professionals who have deep experience analyzing the strategies and returns of public equities, hedge funds, private equity funds, etc.  These are all well defined instruments, within generally limited investment universes, for which substantial data is available.  Even if you are considering seeding a hedge fund or committing to a newly minted PE/VC fund, you can still mine the principles’ track for a fair number of data points.  Furthermore, there are well-established channels for learning about new opportunities (e.g., “capital introduction” dinners) in these spaces.

Now reverse every single one of the above characteristics and you get angel investing.  Every halfway decent startup opportunity is unique, solving unmet needs in different industries – sometimes in industries that don’t even yet exist.  There are no registries or directories of startups, no associations to join.  And you can forget about data entirely with a pre-revenue company.  At best the founders have one or two reasonably successful prior ventures under their belts. (If they had a real home run under their belts, they wouldn’t need investors at all.)  Furthermore, the best way to find great startups to invest in is to know other great startups so if you aren’t already deep in that community, you’re already disadvantaged.

Unfortunately, most family offices don’t realize how fundamentally different early stage investing is from other alternative asset investments.  So they don’t see anything amiss when investment adviser brings them startups to invest in. (I told you I’d get back to step 3.)  They are used to meeting emerging hedge fund managers that way so why shouldn’t they find a great startup that way too?  Because the best startups are never, ever represented by an investment advisor.

Think about it.  VCs are the most networked people on the face of the earth.  VC present at panels or judge pitch events practically every week.  They meet dozens of entrepreneurs every week and know – and have often co-invested with – virtually every other VC in our area.  If a startup founder can’t network his way into a warm introduction to a VC or angel, how is he going to find customers or key strategic partners?  Is this advisor going to be holding his hand then too, after your check has cleared?  Plus, the very fact that the founder thinks he can waive his hand and simply have someone else take something this crucial to his business for him is huge red flag in and of itself.  So any startup that has an investment advisor fundraising for them is already automatically suspect.  In practice, the deals the family offices are being shown by these advisors are the hairy, old, over-shopped deals that every VC and halfway serious angel have already turned down.  It’s no wonder they fail miserably.

To be fair, to the untrained eye they don’t look that bad.  Perhaps they have a cool piece of ad tech that you are convinced will take agencies by storm.  You have to really know the industry to understand why agencies turned them down two years ago when they first tried shopping their solution around.  That fantastic social media marketing tool?  It’s so wonderful that five other companies are already doing it and they are all making better progress than the one you were pitched.  But if you aren’t seeing dozens of startups each month, there’s no way you could be expected to be on top of all these trends.

 

So what’s a family office to do? 

In theory, a family office could hire a seasoned angel investor to invest on their behalf.  But good luck finding one.  Many angels are running their own businesses and/or are entrepreneurs who had a large exit and have no interest in working for a family office.  Also, angel investing is a numbers game.  Most startups will fail, and many of the rest will be modest successes.  You have to invest in many, many startups to have a reasonable chance of 1 or 2 of your investments being a home run.  There’s a reason Dave McClure named his fund (now an accelerator as well) “500 Startups.”

Fortunately, there’s a better option:  Startup Accelerators.

Accelerators(3) are the boot camps of the startup ecosystem.  Companies accepted into top accelerators are the very best, earliest stage startups in the world.  The top accelerators typically get hundreds of applicants for just 10-15 spots.  Having just run the screening process for DreamIt NY’s summer 2014 program I can personally attest that this is no exaggeration.  The odds of getting into Harvard are slightly better than getting accepted into DreamIt.

Accelerators give the startups they accept a little cash ($20k-$40K on average), co-working space for the duration of the program (typically 3-4 months), and extensive mentoring, coaching, and introductions.  Finally, on “Demo Day” the startups graduate by pitching their business to an audience of hundreds of active angel investors hand-picked by their accelerator.  In exchange for all this, the accelerator gets equity in the startup (usually 6-8%) and the right to co-invest in the startup’s seed round.

From the perspective of the family office, accelerators can be the capital introduction dinners for startups.  Unlike the shady investment advisors discussed above, accelerators are personally invested in the startups they accept.  Accelerators do not get commissions on the fund they help their startups raise; they only profit when their portfolio companies have an exit so their incentives are aligned with the other angel investors.

But they are more than just a trusted recommendation from a fellow angel investor.  Accelerators like 500 Startups, DreamIt, TechStars, and Y Combinator invest in dozens of startups each year and can bring a structure and rigor to the investment process that few angel investors have.  Established accelerators bring unparalleled networks and reputation to the table enabling them to source the very best new companies out there.

Many accelerators are structured much like VC funds.  But there is one crucial difference: co-investment.  Even the most co-investment friendly VCs only make their portfolio investments available to LPs if they are unable or unwilling to invest their full pro rata.  If it’s a great portfolio company, the VC will continue to invest until it runs out of powder or starts bumping up against position caps.  And if the VC is able to but does not want to exercise its full pro rata, do you really want a bigger stake in that company?  In both cases, the VC eats first and the LPs get leftovers.

Accelerators on the other hand, rarely invest in more than a small fraction of the portfolio company’s seed round.  As I mentioned above, early stage investing is a numbers game so they reserve most of their investment capacity for new startups.  As a result, 75% or more of the round goes to new investors.

Think about that for a moment.  Here’s an entity that filters out 98% of the startups they see, takes the top 2% and gives them all the help a young company could ask for, and then willingly steps aside and lets any other angel or VC swoop in and invest in those elite new ventures.  No commissions, no membership fees.  Wow.

If all a family office did was go to the Demo Days of the top 4 or 5 accelerators and invest in the presenting startups, the filtering effect alone would give them a high quality portfolio of early stage investments, no additional effort required.

For the family offices who want to build their own experience base and startup network, there is an even better option: invest directly in the accelerator.  Accelerators typically give their LPs early access to their new class so LPs can track a startup’s progress over a longer period of time before deciding to invest and/or can invest before Demo Day and avoid the risk of missing out on the hottest prospects.  Furthermore, most accelerators will gladly explain their selection process, describe how they are assisting the startups, and introduce LPs to other members of the startup community.  This practical education is not something you can buy anywhere but you can get it for free simply by investing in something you already want to invest in.

Investing directly in a top accelerator also makes sense from an efficiency perspective.  Even investing the bare minimum $25K per startup (and some startups insist on $50K or $100K minimums), creating a portfolio of 100-200 startups would cost a family office $2.5M-$5M.  But this leaves no money for follow on investments.  As a rule of thumb, you want to set aside $1 for follow on investments for every $1 initially invested so getting that 100-200 startup portfolio actually means committing $5M-$10M to early stage investing.  In contrast, you could invest $1M (4) into the accelerator’s fund for the same portfolio of 100-200 startups, including follow on investments.  That comes out to just $5K-$10K per portfolio company.

So let’s re-write the family office story:

  1. A family office decides it wants to get into angel investing.
  2. It researches the accelerators in its area and invests in 1 or 2 of them.
  3. It spends the first few accelerator cycles learning the ropes and making connections.
  4. As it gains confidence, the family office invests directly in a few of the accelerated startups, effectively doubling-down on a few, high conviction plays.
  5. The diversified portfolio does well
  6. The family office makes disciplined, intelligent, efficient angel investing a formal part of its allocation strategy

Now how’s that for a happy ending?

 

(1) Just in case you were wondering, “For fools rush in where angels fear to tread” was first written by Alexander Pope in his poem An Essay on Criticism.

 (2) Right Side Capital analysis of eight large studies of historical angel investing returns in the US & UK (http://rightsidecapital.com/assets/documents/HistoricalAngelReturn.pdf

 (3) Sometimes called incubators, although incubators are more often shared co-working spaces with some additional services that are of value to startups.  Unlike accelerators who rigorously screen their applicants, incubators are generally open to all, space permitting, as long as they can pay the rent.

 (4) Many accelerators will allow family offices to invest as “individuals” rather than “institutions” enabling them to qualify for minimum investments of $500K or even as low as $250K, which comes out to as little as $1,250 per startup(!) 

100% of Nothing

“We are just not sure it’s worth 6% of our company.”

Accepting the position of Managing Director in charge of DreamIt’s NY startup accelerator meant a lot of things, two of which include:

  1. Meeting a lot of really, really interesting startups  :-)
  2. Far less time for blogging  :-(

One recent experience cut right to the core of the accelerator experience and has been bothering me so much that I’m going to share it despite having far more pressing items to handle in the one week I have left before DreamIt NY Summer 2014 kicks off.

We receive hundreds upon hundreds of applications for the summer accelerator cycle and meet with (in person or via Skype) over 50 of them before winnowing them do to the 10-15 companies we accept into this program.  Despite the long odds – you are actually statistically more likely to get into Harvard than DreamIt! – you may be surprised to hear that not every company we extend an offer to ultimately accepts.  Most of the (small) handful of companies who decline do so because they want a few more months to work on their business before entering our program.  As DreamIt has accelerator programs every few months, our philosophy in these cases is generally, “We liked you now, we’ll love you even more after 3 months of further progress.”  So if I’m sad not to have them in DreamIt NY Summer 2014, my colleague Patrick FitzGerald will be thrilled to have them in DreamIt Philly Fall 2014.

One of the startups we accepted, opted to go into a different accelerator program.  We ‘win’ far more than we ‘lose’ but I won’t pretend this doesn’t happen from time to time.  I think they made a mistake, especially given the nature of their business and the industry they are in, but the other accelerator runs a good program as well.  So now I know how Harvard feels when a student they accepted goes to Yale instead.  This isn’t the situation that bothers me.

One startup we accepted signed the offer letter and we both began making plans for the summer.  Then I get a call from the founder to say she was having second thoughts.  Would we be able to find the right mentors for her startup?  Could we make useful industry connections?  By the end of the call she stated that her team felt that they would rather just continue working out of her parents’ basement than give up 6% of their company to an accelerator.

Let’s ignore the fact that these were all questions that should have been asked before signing our offer letter – ideally even before applying to an accelerator program – and focus on the core complaint: is an accelerator program worth 6% of our company?  For the answer to be Yes, a very simple equation has to hold true:

EV(startup+accelerator)*94% > EV(startup)*100%

In other words, is the Expected Value of 94% of your startup with the accelerator’s help worth more than the Expected Value of 100% of your startup without any help?

So how do we think about the Expected Value of a startup?  Let’s simply the problem with some hypothetical numbers.  Let’s assume that a “success” means that your startup sells for $100M and that the “odds” of success are 1:100 or 1% (note: I’m a huge fan of making the math easy).  In this case:

Expected Value = $100M * 1% = $1M

(hmm… I wonder if this is why so many priced seed rounds are at a $1M pre?)

So for the accelerator to be at least as good a deal as going it alone, the odds of success have to be high enough to get you to a $1M+ Expected Value despite giving up 6%.  Let’s whip out the calculator and solve for x:

94% * $100M * x% = $1M

x% = 1.064%

So, whether they understood this or not, what this startup was saying is, “We think your accelerator cannot increase our odds of success by even 7 one-hundredths of a percent.”  Wow.

Now there are a lot of new accelerators out there and I firmly believe that some (many?) of the newer ones with no track record of nurturing successful startups, no real network of experienced, well-connected mentors, no built-in audience of hundreds of active angel investors – these accelerators probably cannot move the needle when it comes to increasing a startup’s odds of success.  In fact, entering into a poorly regarded accelerator may even reduce the odds of success due to the negative signal.  But to think this about an accelerator with a six year history in five cities where over one third of our ‘graduates’ have collectively raised over $115M and who are now worth in aggregate over $410M, that’s mind boggling.

Now I like these entrepreneurs and I honestly and truly hope they succeed despite this decision but I fear that they have just made a horrible mistake.

Thanks for letting me get that off my chest.  Now back to work!

 

 

Two must-have, time-saving, super-easy productivity tools: Evercontact & Boomerang

I love these two services so much, I’ve not only paid for them, I have even added them to my email signature.

Why? Since this post is about time-saving productivity tools, I’ll be brief.

Evercontact (http://bit.ly/LDNVL5)Image
I used to spend a lot of time copying and pasting names, phone numbers, emails, addresses, etc. out of emails I’d received into my Address book.  Evercontact (formerly WriteThat.Name) changed all that.  It automatically scans incoming email, identifies signature blocks, and imports the data, creating new contacts and updating existing contacts.  There’s a fully automatic mode where this happens entirely behind the scenes and a manual mode where they periodically alert you about new contact information that you can opt to save or ignore.  There’s even a feature where they will retroactively scan your past year of email to extract the contact data there.  It doesn’t get any easier than that.
Special shout out to Brad Patterson, the face of evercontact.  Hit reply to any email you get from evercontact and he actually responds, often within hours.

(Yes, I am aware of CardMunch but that app is inexplicably still not available for Android.  Plus, I get fewer and fewer business cards these days.  I still get some, though, so I’m looking into CamCard for that.  Stay tuned!)

I had heard about this service long ago but hadn’t got around to trying it until recently and I’m kicking myself for all the time I could have saved.  I send a lot email where it’s on me to make sure there is follow up (e.g., intro requests email, bizdev proposal, etc.).  I used to send the email and then manually add a reminder to my calendar.  Boomerang plugs into my Gmail account and adds a 2nd row of options to the Send Email screen:
Image
I simply check the box, decide how long I want to wait, and hit Send.  If there’s no reply in that time period, Boomerang automatically sends the email back into my Inbox.  So much less effort and my calendar is so much less cluttered.
I don’t use the Send Later feature that often but it is sometimes useful when I’m working over a weekend but don’t want my email to get lost in the Monday morning email flood.  You can (and I used to) simply save an email to Drafts and manually send it later but this is one less thing to remember.
While Boomerang’s Gmail plug-in works wonderfully, my one disappointment is their app.  The Boomerang features are not (cannot be?) added to the Gmail app so if you want to use these features while on the go, you need to install the Boomerang app.  I like the swipe-left-for-additional-options interface (right swiping an email will archive it, just as on the Gmail app) but the Boomerang app appears to show me all my emails, not just the ones in my Inbox or Priority Inbox.  Also, Boomerang doesn’t update as quickly as the Gmail app and occasionally fails to connect at all.  If they could replicate my Priority Inbox view in their app and fixed the updating issues, I’d probably make the Boomerang app my primary way of checking Gmail on my phone.
If you try these service, let me know what you think.  And of course, if you have other great productivity hacks that you think I should know about, I’m all ears.

Angel Profile: Zach Aarons

alleywatch-logoNote: Angel Profiles is a bi-weekly column appearing on AlleyWatch.  

Angel Profile-Zach Aarons

How did you get into angel investing?
I was running a walking tour business here in New York. My partners and I were always playing around with how to make the experience better. We had a lot of ideas and then, with the launch of the iPhone 4, other people started doing it. I got depressed for a bit, that I wasn’t the first mover, that they stole my idea. Obviously they didn’t but they were actually executing when I was just doing walking tours. So I decided to start calling and emailing these people out of the blue and asking them if I could get involved. They said I could invest. I had no idea about seed terms and any of this stuff but I took the plunge, started writing checks, and I got addicted to it.

What was your first angel investment? How did it turn out?
I was doing consulting work for a digital agency downtown that I still advise called Gin Lane Media. They were developing wire frames for me to build an artificial intelligence itinerary generator. I had to go out to LA for work and TechCrunch Disrupt 2011 was feeding live videos of the presentations. I saw this guy present an artificial intelligence itinerary generator called Weotta and it was far better than anything I could have ever done. I emailed one of my friends who was there at the time and said, “Don’t let this guy out of your sight. Don’t let this guy leave until he agrees to take a check from me.” I ended up investing. I called Gin lane and told them to burn the wire frames.

The company is doing really well. The founder is really well networked in the valley and has received investments from far more impressive people than me. It was really a watershed for me because he took a chance on an (at the time) unknown investor when he didn’t have to. More importantly, he has become one of my closest friends, a mentor to me, and has introduced me to more people than anyone else in the tech scene.

What investment do you most want to brag about / why?
Everlater is one of my exits. Two guys travelled the world together and decided they wanted to do a mobile travel journal app. Which failed, as all mobile travel apps do. So they pivoted and became a B2B platform that sold solutions to tourism companies. Rafting trip guides and school trips and things like that could own the content rather than all the content being creating on these trips were going elsewhere – Facebook, Twitter, Instagram.

They got funded by a VC fund in Boise, Idaho called Highway 12 Ventures and were looking for other angels. I remember seeing their pitch deck on Skype while in my in-laws house in France. The last slide in the deck is a picture of them standing on this giant crater. I said, “Where is that? The Atacama Desert?” And they said, “Yeah. You’re the only person we pitched that has actually gotten that.” I wrote them a check for $25K. I had a connection to these people. I couldn’t explain it. I was the only angel to take the plunge along with the VC fund.

Less than a year later they got bought out by AOL Mapquest who, rather than compete with Google Maps, are pivoting to a travel solution.

But why I’m most proud of this is that, while I was helping them through this transaction, they told me, “This deal took longer than we expected. Without your $25K, instead of getting acquired and having a really nice exit, we would have gone bankrupt.”

Notable train wrecks and lessons learned?
<Laughs> Do I have to name the company?

I invested in this company. Four guys, right out of college, hungry as hell, very talented, knew their market. They had ambitious plans and moved out to the valley. A couple friends and I were the first money in for $50K each. They raised about $1M in 9 months… and blew it in 9 months. No investors knew that they had been burning money like this. Maybe their advisors knew but none of the investors.
First lesson learned: If a company has really impressive advisors but none of them are writing checks, figure out what is going on.

We were told they were going to merge. Basically, it would have been like a talent merger. We were excited because the company that was coming on had a very talented IOS person. The team continued to look impressive on paper. It should have been a red flag how excessively aggressive the CEO was but I looked at it as being stupidly hungry, really wanting it. There’s a fine line there.
Second lesson learned: Try to figure out where hunger ends and excessive asshole-ish behavior begins.

Then I get a call from him saying, “The guy who was going to merge reviewed the bank statements decided to back out at the last minute. The other two cofounders also backed out. The company is folding. We have no money. We’re $150K in debt.” They had been spending money like crazy. We found out the company had bought a $60K automobile.
Third lesson learned: Monitor how your companies are spending money if you can.

Then it was just a shit-storm. The founders were threatening to sue each other. We were thinking of seeking legal action but there was no money to be recouped. The founder would fire off these emails insulting a lot of the investors, calling them names. The company folded.
Fourth lesson learned: Do your diligence on founders.

What startups have you backed that should have hit but didn’t and why not?
There are plenty that didn’t hit but I don’t know why.

What’s the most humbling or frustrating experience you have had relating to angel investing?
There was a company I had been working with on and off for about a year and had a very good relationship with. I always told them, “Whenever you guys are raising money let me know. I love your product, want to work with you.” They get into Techstars. All is good. Then they raise a sizable seed round and I get a call, “We are kicking about 10 angels out. The lead investor doesn’t want that many angels in the deal.”

Your day job is at a real estate development company. How does that compare to angel investing?
My dad is in real estate so I have always been around it but I hadn’t worked in real estate until after angel investing.

It is a completely different world. In IT, you incubate a concept and in two weeks you have a products. In another two weeks you raise a round. Then you sell the company two weeks later. Millennium Partners does large scale, mixed-use development. These projects take ten years: Three years to get your entitlements, two years to get your financing, three years to actually build the building, and then another three years to sell it out. So it is a very long slug and I come in and out of deals at times when I can add value. It’s very, very different.

Where it helps is that there are a lot of very interesting start-ups popping up in real estate tech. For the first time real estate is starting to embrace enterprise products. I have been lucky enough to participate in a couple of those deals and I hope to do many more. I am even thinking about incubating my own real estate SaaS product right now.

You were a Senior Associate at ENIAC Ventures for a while. How was that?
ENIAC is a small fund and this was not a typical kind of Associate position. The partners all have full-time jobs, I had a full-time job.

How I got involved with them is pretty funny actually. I met Aamer Abdulla, a very active angel, who invested in Vic Singh’s company Tracks, a photo sharing solution. [note: Vic is also General Partner at ENIAC.] Aamer thought I should take a look, introduced me to Vic, and we really hit it off. At the end of the meeting he said, “So can you write a check?” I said, “I’ll write a check Vic, but only if you let me intern for you at ENIAC”. He said, “I can’t do that but I’ll introduce you to the other partners. If they like you, they’ll show you the ropes.”

It was a great experience and they were kind enough to let me in on some of the deals they are doing, such as Sonic Notify and TapCommerce.

Pretend that it’s 2019 and complete this sentence, “[Technology X] is less than 5 years old and now I can’t imagine life without it.”
My smart fridge. It is going to have spots in it for everything – water, milk, orange juice, cheese, whatever. Whenever things get taken away for a specific amount of time (viz., eaten), it will automatically be delivered to my house so I can put it back in my fridge. Automatically replenished.

The other thing is my personal, flying drone. He takes out the garbage for me. He mails letters for me. (It is only 2019 so there will still be letters.) My hovering personal butler. I can’t imagine life without him.

What’s the best way for entrepreneurs to reach out to you?
Get a warm introduction. If you can’t do that, I am unlikely to invest. My AngelList profile is a pretty substantial guide to my past investments and you can find someone who is friendly with me via Linkedin.

If you are an active NY-area angel (or know someone who is) and would like to be profiled for AlleyWatch, please contact me here. 

Angel Profile: Randy Adler

alleywatch-logoNote: Angel Profiles is a bi-weekly column appearing on AlleyWatch.  

Angel At A Glance-Randy Adler

Randy Adler is the Co-founder and Managing Partner of RK ADLER LLP.

Why do you angel invest?
I love the space.  I think it is the opportunity of a lifetime: a true land grab.  We are experiencing a transition from the old economy to the new economy in which all things become “tech.” This is a unique point in time.  It’s not just a “pop market” that – you ride and get out.  It’s not just a paper game.

Overall, I like to invest in companies that actually make gut sense.  Right now the most opportunities are in technology, especially B2B startups that are generating revenue by helping old brick and mortars transition to the new economy.

When and what was your first angel investment?  How did it turn out?
In tech, my first angel investment was in Lumier.  I co-invested alongside SV Angel, Founders Fund and some other notable investors.  The founder is a former Microsoft developer, a brilliant young guy named Cullen Dudas.  He was recruited at a young age – something like 13.  Basically, he created a new operating system to make Windows 8 look more like the old Windows and function better for people who are more familiar the traditional interface.

It’s doing ok so far.  Every new company has challenges and this one is no different. I’ve been taking more of an active role in this one in order to help them along.  This company has promise because of the high-quality talent, intellectual property and the high quality investors who are involved.

What investment do you most want to brag about and why?
I think I am most proud of my involvement with Vine, the 6-second video clip company that Twitter recently acquired.  I was part of the founding team as an advisor and was involved every step of the way from pre-formation through exit.  I am very proud of what Dom [Hoffmann], Rus [Yusupov], and Colin [Kroll] – the Vine co-founders – have built.

Any notable or amusing train wrecks?
There was a geo-location based company I invested in during the hype of the B2C, sexy-this-is-going-to-change-the-future, wave in 2011.  They were extremely well capitalized but they made a lot of cart-before-the-horse mistakes and their burn was very high.  It was a really good lesson to me.  Just because you have a company with a lot of money behind it, some great names, and everything else, doesn’t necessarily mean that it is going to be a hit.

There is another very similar story that was a fashion company.  Also extremely well capitalized, great VCs involved… and just completely mismanaged.  They had a lot of visionaries but were not great day-to-day operators.  How do you tell the person whose baby it is that they need to give up their baby?  It is a really tough transition.

Were there any companies that you wanted to invest in but couldn’t?
numberFire.  I love those guys.  I think they are brilliant.  They are an ER Accelerator company that I wanted to invest in before they were hot.  But I just did not pull the trigger in time.  For me, they are the one that got away.

Most humbling experience (relating to angel investing)?
It is a tossup between missing deals because I couldn’t pull the trigger fast enough – I like to take my time and I do more due diligence than some angels – and being passed over in favor of more “strategic” investors.  I definitely understand why a startup would want strategic investors and now that I have established more of a name for myself, it is less of an issue.

What do you like to see in a pitch?
I actually get nervous when a founder has an amazing pitch.  I think to myself, “What am I missing?  This is too good to be true.”  You get some tech guys who just do not pitch well and it does not mean it is a bad team or a bad startup.  I think it is up the investor to cull out the critical things.

A quality product and a great team means a lot more to me.  If the founders are working hard on product, I don’t expect them to be master presenters and memorize Guy Kawasaki’s 10/20/30 rule of PowerPoint.  At the stage I invest in, the companies generally do not have a marketing guy on the team… and if they did, I would be worried that their burn was too high.

What makes you better (e.g., more helpful, more valuable) than the average angel?
I understand that there is sometimes going to be bad news and that everyone makes mistakes.  It means I can help.

Also, I think I’m uniquely positioned as a Co-founder of one of NYC’s top law firms for startups.  I’m also really tuned into the startup community on both the east and west coast.

Pretend that it’s 2019 and complete this sentence, “[Technology X] is less than 5 years old and now I can’t imagine life without it.”
The next innovation will be something in the Google Glass realm – hardware based.  It will be something like smartphones but even more integrated into our lives, either wearable, embedded, or something that we swallow.

What’s the best way for entrepreneurs to reach out to you?
Through the Interwebs of course. J

They can contact me via email: randolph@rkadler.com. I’m also on LinkedIn and Twitter @RandolphAdler

If you are an active NY-area angel (or know someone who is) and would like to be profiled for AlleyWatch, please contact me here. 

Angel Profile: Mark Wachen

alleywatch-logoNote: Angel Profiles is a bi-weekly column appearing on AlleyWatch.  Here’s the original article.

Angel At A Glance-Mark Wachen

Mark Wachen is the Managing Director for DreamIt Ventures New York and the Managing Director and Founder of Upstage Ventures.

What got you into angel investing?
Mostly my experience with my own company, Optimost. [Acquired by Interwoven, which was in turn acquired Autonomy Corporation, which was bought by HP].  When I started that company, I raised some angel money.  The role that those initial angels played was instrumental to the company’s success.  The ability to contribute that same experience to other entrepreneurs to me is intrinsically valuable.  Also, I am a big booster of the New York tech scene, and one of the key reasons for its growth in recent years has been the much stronger group of angels and the early seed money that is now available.  It really helped ignite the whole thing.  Like Bruce Springsteen says, “You can’t start a fire without a spark.”  Angel investing is the spark that gets the whole thing going.

Certainly I hope there will be real economic returns from my angel investing but that’s not the only motivation.

What was your first angel investment and how did it turn out?
The first one was a company called Order Groove.  They are basically a subscription commerce platform allowing eCommerce sites to offer recurring orders-of-the-month club functionality to their websites.  I invested in 2009 and they are doing really well.  They just raised a Series B round and have clients like L’Oreal, Jockey, Johnson & Johnson, Grainger, and others.

It really resonated with me because they faced some of the same challenges I faced in the early days of Optimost.  Early on they faced the question, “Why can’t companies just build this themselves?”  What I’ve learned from my own experience is that, while probably anyone can build anything with enough time and resources, none of these big companies have the time or focus to do it.  So if you can provide a critically valuable service, they will gladly pay to have someone else provide it.

What investment do you most want to brag about?
(laughs) It’s hard to say who your favorite child is.  I guess I have to pat myself on the back that virtually all of my angel investments are still in business.  I consider that an accomplishment.

One that I think is particularly interesting is YouNow.  They are a next generation, interactive television platform.  There offer a huge variety of channels where people perform for a minute and the audience votes thumbs-up / thumbs-down.  If the performer gets enough votes, he gets another minute.

What’s exciting to me is that it seems like the logical progression of where interactive entertainment is going.  They are doing really well and now  have a large number of  channels going 24/7, with all kinds of interesting content.  And the fact that it is crowd-curated means that quality should just keep getting better.

Notable lessons learned?
I had one train wreck.  It’s still going but it’s a train wreck.  This was a movie deal.  I certainly learned the lesson “invest in what you know” because there was a lot about that particular industry that I wasn’t aware of.  And, at least in this particular case, the level of unprofessionalism and mismanagement was the kind of thing you read about (laughs) or see in movies.

What’s the main reason you see for startups you backed, either personally or through DreamIt Ventures, that should have hit but didn’t?
At least for early stage companies, the common theme is usually team dynamics – not that it is not a quality team but that the founders don’t get along with each other and that causes the whole thing to implode.  We as investors are constantly talking about how you need a well-balanced team with all these different skill sets and the side effect of this is that sometimes, in an effort to satisfy investors, it inadvertently leads to shotgun marriages, which are usually not a recipe for success.

Most humbling experience (relating to angel investing)?
The most humbling are the ones that get away, the ones that for whatever reason I decided not to invest in and that I kick myself for now.  One I can mention is Birch Box.  I met the women who run that right when they had the idea, before they graduated from Harvard Business School.  They were a really impressive team and had a really novel idea.  The challenge I had was that they were going after a category, women’s cosmetics, that I just didn’t have domain expertise in so I had a hard time wrapping my head around the market.  But they checked out really high in every other metric and they seem to be doing really well.

How has running DreamIt NYC affected your angel investing?
They complement each other really well.  My own angel investing, while in the grand scheme of things are certainly very early stage, within the spectrum of early stage, are not quite as early as DreamIt’s investments.  A company that is coming into DreamIt is probably too early for me.  I would probably think it needed more traction.  So it works out quite well.  If they are too early to me, they may be a great fit for DreamIt.

What’s the smartest thing someone you invested in did?
One of my investments is a company called Thumb [recently acquired by YPulse].  They basically provide real-time feedback on anything.  The speed is astounding, meaning that you post the question and within minutes you can have a hundred responses.

When I met with the CEO, Dan Kurani, early on, the product demo was the perfect example of actions speaking louder than words.  In the meeting, I asked questions on Thumb about random topics and within minutes answers started coming in.  Experiencing the product in real-time was just an incredible proof of concept.

What’s the dumbest thing entrepreneurs do?
The kind of continuous dumb mistake I see is companies reaching out to me without doing any homework at all.  Just because our names show up on a list of top angel investors does not mean we are going to be interested in what they have.  There is such an enormous difference between just reaching out via LinkedIn blindly versus providing a rationale for why you are specifically targeting me because of something in my background.

What makes you better, more helpful, more desirable, etc. to a startup than the average angel?
First of all, I’ve walked in their shoes because I was an entrepreneur myself, raised angel money, grew my company to 85 people, and exited.  On the flip side, as an investor and even prior to starting my company while I was at Sony, I sat on the side of the table with VCs and other professional investors.  So I think I bring a multi-dimensional perspective on what an entrepreneur might be thinking – what are the things that motivate and are important to an entrepreneur – as well as what’s important to an investor.

What kind of returns do you aim for and how do you track ROI?
I don’t have a precise mathematical model but I’d like to feel confident that there is a reasonable path to at least a 10x return.  My expectation is that it could be five years before I see a return.  I know it takes time.

I’ve only had one exit so far, Chai Labs [acquired by Facebook] and the rest are still in progress.

Pretend that it’s 2019 and complete this sentence, “[Technology X] is less than 5 years old and now I can’t imagine life without it.”
Self driving cars.  I expect this to become much more mainstream.  Even though it may be hard for people to wrap their heads around, the ability to make that time in the car productive is very valuable.  And the technology is already strong.

What’s the best way for entrepreneurs to reach out to you?
LinkedIn… but read my bio first!  You can also see my AngleList profile for more background.

If you are an active NY-area angel (or know someone who is) and would like to be profiled for AlleyWatch, please contact me here. 

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