Here are two contrasting startup stories I've seen firsthand.
With one company, a founder and his super inspirational, creative, and established buddy hatch a plan to build a very strong content brand that serves as a platform for a lot of diverse revenue streams--events, ecommerce, advertising. You could think of it as a spin on Thrillist. With the author staying close as an advisor, they build a real, cashflow positive business and start to think about where they could go with some outside capital.
One of the big opportunities for them is audience development--driving event attendees to the content, events to the readers, and doing some low-hanging fruit upgrades to their social strategy. They find a kick ass, experienced content person to advise them for six months and help them build out a team around this.
The fundraising will be for that content team, additional developers, and salespeople to leverage the unique brand they've built. Nice, tight story that makes sense. I certainly would have wanted to be an angel investor in Thrillist at the time.
The second startup came to me from a founder of a company that I only found out later wasn't fulltime. The first pitch I got was from someone who didn't intend on staying with the business as an employee. It's actually the first time that's ever happened to me, so I honestly never thought to ask. Everyone I've ever gotten pitched from can't wait to quit their other jobs to work on what's being pitched. When I found out, I was super disappointed--not because this person was even the right person for the business--but because I liked the first person I met, and then had to mentally extract him from the story arc of this business.
That wasn't the only stumble in the business. The team told investors they were hiring a C-level employee, and, upon diligence, it turned out that the person didn't want the job. Not only that, but they actually took that potential hire to a fundraising meeting with a VC--a VC that was interviewing this candidate for another position the next day.
On top of all this, there's never been a really tight story about goals and resources around the funding--exactly what the next five hires will be, etc.
Here's the interesting thing:
It's the same company.
Neither one is a false account, but in the latter situation, the team pitched at an awkward moment and were super transparent about how the sausage was being made.
Every startup has been in flux at one point or another as to founder roles, key hires, and plans. Not everyone who has ever been around at the start of the company is the right person to move forward. These things are nothing new.
What you have to be careful of is how the story appears to investors. Are you hitting the fundraising trail at the right moment where you've got your plan together, team in place, and know where you're going?
Even if you pitch super early--it's totally fine to tell an investor you have some key open questions, and then come back when you've got them solved. That's often how relationships are being built.
It's that awkward middle phase--where you're trying out a bunch of stuff, seeing what sticks, that you want to be careful about story arc. Sometimes you meet an amazing person who has no intention of ever being fulltime on anything. You don't want to tell investors you're trying to get this person and then have to tell them you failed. Hiring a consultant who always intends to be a consultant isn't a failure. Maybe you thought you could snag them, but still, this person could be great for a short stint and a real plus for the company. How is that story being told? How is the story of how the founders are figuring out their roles being told?
I'm a big fan of transparency, but if you're going to go far and wide on a pitch, organizing your story is key. It's a bit like inviting friends to your apartment for the first time. We all know that our places can be in various states of disarray at times--but that doesn't mean that if you know you have guests, you shouldn't throw your dirty socks in the hamper and wipe off the counter.
I still feel like it's never too early to talk to an investor to get feedback, but before you do, think about how your company came together. Think about story arc. What's the truthful, transparent account of what's going on that shows our best times ahead of us. Otherwise, you're just starting a game of Jenga and asking an investor to take out the bottom piece.
I'm still very much in talks with this company, helping working through the story now that I know what's up--but I'll admit to experiencing some mental pain experiencing the story in mid-flux and development.
Greg Galant of Sawhorse coined a term yesterday that captures perfectly what I thought of my 8th SXSW. We were having a discussion about big brands taking over the scene and he called it "conference gentrification". That's exactly what has happened down in Austin. The small startups and individual creatives were early to SXSW and created a great, authentic experience over many years--a "neighborhood" if you will--with a certain attractive vibe.
Brands, in search of interestingness, flocked to SXSW in search of the next cool place to be, like young executives moving into the big glass luxury buildings on the Williamsburg waterfront. What was once the GroupMe Grill--a stunt to buy out a little food shack across from the convention center that gained conference-wide attention--has become the Citrix GoToMeeting grill. Deloitte had a booth in the convention center where Twitter flat screens once stood seven years ago before anyone knew about the startup service.
I might sound like I'm shaking my fist saying "Back in my day!" and "Get off my lawn!" but this isn't necessarily all a bad thing. It's just different. New York neighborhoods that experience growth and change may lose that authentic feel, but they gain much needed economic activity while crime tends to drop. SXSW has become a fun way for lots of brands to interact with startups and creatives--different but not the same.
Every conference has its own neighborhood. The Collision Conference, for example, sold out right away because it comes from the same folks that put on The Summit. Those conferences feel a lot like a planned suburban neighborhood. They have no long organic history, but everything is beautiful and setup exactly the way you want it. A park near a lake, a school, and a three car garage--complete with Bill Clinton, Elon Musk and Snoop on stage prognosticating the future of civilization.
Other conferences will always feel like Red Hook--out of the way and tough to completely gentrify because of a lack of public transportation. Those are the hacker and designer conferences and the Bar Camps--not easily accessible to the general public but quite worth going to.
I love Red Hook and I love conferences like that. I'm looking for more. I want to spend more time with people who aren't big names where everything at the conference isn't perfect. I met Raul from Tinybop at the first Brooklyn Beta--a community run conference that had two investors and 148 designers, devs and creatives in attendance. Like the stereotypical white dude that has little interest in living next to other boring white people I'm the VC that wants to find out where the other VCs aren't.
I'm fully aware that makes me the conference gentrifier, but my hope is that where I go can stay under the radar for at least a little while before my kind changes things.
About seven years ago, I wrote a post on breaking into venture capital and I continue to point the five or six people a week who ask me how to break into venture.
Today, I want to add two addendum to it, based on the work of two up and coming women in the NYC tech community.
Yesterday, Amrit Richmond announced her new employment at RRE as Director of Community & Platform. The key to her getting the job was that she had essentially started doing the job long before it ever got announced. She had been running social media part time for a smaller fund and had built up a following with her own tech newsletter. No one was paying her to write the newsletter, but most of the team at RRE was already on it.
When Amrit was applying, I told her she was a lock for the job. When she asked why, I said it was because if anyone was better qualified, we'd already know about them by now. The candidates for venture capital roles are already out there and usually in plain sight and there simply wasn't anyone out there doing what Amrit was doing who wasn't already fulltime at a firm.
Another case in point, Spark Capital just hired Kate Bolin--someone that had been interviewed at a portfolio company of theirs that had made a good enough impression that they labeled her as someone to stay in touch with.
If you need to introduce yourself to a VC firm, you're probably not getting the job.
The opportunities, however, are different than they used to be. At the early stage, the ranks of the non-partner investor are disappearing. VC firms are going back to being mostly partner driven shops, where dealflow and decisions stay up top. They are, however, staffing up with specialists. Like lefties out of the bullpen, VC firms now have recruiting partners, pr and marketing experts, technologists-in-residents--and USV even has an on board activist. If you can't walk into a firm and tout a specific skill that is a benefit to portfolio companies, you're going to have a very tough time getting in.
And no, analyzing startups is not a portfolio company benefit. That's a benefit to the VC firm. To the company, as a recently minted MBA with no startup experience who wants to run the 4th year numbers, you're just a pain in the ass.
One thing that I see too many people moving from the finance world doing, both in attempts to get into VC and to startups, is relinquishing the resources they have at their old job. They can't wait to get out of their bank or consulting firm, but they forget that they have connections to something that startups want desperately--money. If you want to break into the startup world and you come from investment banking, don't forget the one thing that your resume says that actually speaks to entrepreneurs--you know potential investors.
Christina Bechhold didn't forget that--and so she co-founded her own angel group. It's a group of her peers from the professional world--up and coming titans of finance and consulting with good salaries and not a lot of dependents. She and her co-founder Graham Gullans went around to all the other early stage investors in NYC to learn best practices, and present themselves as a good potential co-investor. There's really no easier way to get into venture than to find some money, reach out to smart folks to learn, and start writing checks. Being good at it takes a bit of luck, hard work, skill, etc., but in a city like New York, with it's access to capital, "getting in" shouldn't be the hard part.
The NYC startup community maintains a positive, supportive atmosphere. We celebrate a strong effort.
However, that often makes it hard to tell who actually excels at their job and who just mails it in or got lucky. This goes for founders, employees and investors alike.
I was just noticing that a professional acquaintance of mine just changed jobs for the third time in two years--going from startup to startup to startup without, ostensibly, accomplishing much at any of the companies. They certainly didn't become huge successes. Yet, for some reason, everybody seems to think he's really good at what he does. Why?
The same goes for investors. There are a few obvious investors with great track records of repeat success, but when's the last time you really tried to value an investor's portfolio. That VC speaking on the panel, are the deals you know about really doing that well? They raised more money, but when? How long ago? At what valuation? Are they making real revenue? Are the exit prospects for the company any good?
Even if their record looks good because of that deal, was it really their deal? Did they lead it? Will the entrepreneur count that investor among their most helpful? Would the entrepreneur enthusiastically include them in the syndicate of their next venture?
There are a lot of founders with questionable records, too. If someone bought a company for $50mm after a year, before it became a business with actual revenue, what are you really crediting the entrepreneur with? Could you really call what they did building a business?
There's really no substitute for research. If you're going to pick an investor, hire someone or invest in a founder, you need to figure out what they specifically did to create value--and how what they did was something unique to them. Could anyone have done what they did, or do they have their own special way of creating magic?
We need to raise our expectation level--especially in the media, on panels, and in our everyday discussion. Let's be a little more discerning when we're dishing out praise. Let's figure out who actually went above and beyond, versus getting lucky riding a wave.
Go pitch a VC with an idea, and they'll tell you to build it.
Go to them with a prototype and they'll tell you to launch it.
Launch it, and they'll tell you to get more users.
Get users and they'll tell you to get paying customers.
Get paying customers and they'll tell you to get bigger, enterprise clients.
Get enterprise clients and they'll tell you to get them faster, because it seems to be taking too long.
It frustrates me to no end. If someone actually did check all these boxes, it would be a Series B deal, not a seed investment.
Last I checked, taking risk, and being ok with uncertainty, is supposed to be our job. No risk, no return.
Technology is moving faster, markets are changing more quickly and uncertainty seems to be increasing.
In my mind, that creates the opportunity for increasing returns. New markets are available. We're doing things in personal health, mobile, and physical products that we never could have done ten years ago. TVs are changing. Finance is changing.
Risk, over the long term, is going to be rewarded, but there are no sure bets. Let's remember that, people.
If you're not cool with risk as an investor, may I interest you in some very nice fixed income jobs.
*This post was not directed at anyone specific.