A first date playbook for founders.
I sucked at dating.
Here’s how it went almost every time. After a strong opening full of storytelling and chivalry at a carefully chosen venue, I stumbled sooner or later. Like a clock. I inevitably turned off my new friend with an awfully arrogant comment, a distasteful joke punctuated by a loud laugh or an intense monologue that delved too deeply too early.
If by any chance I went through the first encounter without a screw-up, I was so surprised that I froze, unable to make the next move. I made other bad choices too. My exceptionally handsome cousin was my wingman of choice. Having him next to me, up for grabs, was a major drag for my dating career.
Yes, I still feel a bit out of sync with the world. Thank god I’m not looking for mon grand amour anymore.
Luckily for me, raising capital is not dating.
However, there are certain similarities; namely, the dance and that curious exploration of what’s possible. If anything, you need to nail the first meeting to have a chance to find a great partner.
Some first pitches fail to get entrepreneurs a second meeting because there’s just not a fit or the timing is off. Other times, meetings that are going very well at the start can end a process with a single mistake. I hate that as much as you do.
Here’s a list of the major turn offs I’ve experienced during a first meeting that you can and should avoid. Nailing a meeting with a partner can turn the firm into high gear to learn more from your company. You want this momentum. Moreover, if you barely got a second meeting, the bar for conviction suddenly becomes higher.
For the purpose of this post, I’ll assume you don’t make rookie mistakes. You are on time for the meeting, do not take the first call from an Uber, send materials beforehand without asking for an NDA, research the basics of the person and firm you’re pitching to, and do not fight your cofounder in the middle of your presentations.
Was that a lie?
Trust is critical in the venture business. It needs to be mutual. It is nurtured by action over years. In parallel to building conviction around your team and business opportunity, the investment process generally seeks to find the seeds of mutual faith.
It is not surprising the biggest turnoff happens when you send bad signals about your honesty. Investors know you will sell your best version, but you should never lie. Period. Never make up numbers, facts, or round progress. Most of the time it’s not worth the trouble and it shows. I can only operate with a high degree of trust so when I hear about your progress with another VC, the almost closed enterprise client or the big progress in unit economics, I remember and I check.
As they say, if you tell the truth, you never have to remember anything. Latin American founders rarely say ‘I don’t know’ or ‘let me check that and get back to you’ in a meeting. It’s a sign of strength not only with investors but clients. Add this to your pitching arsenal.
I remember one incident where a guy was so freaked out by something that as soon as his date went to the bathroom, he had to tell the bartender I was working with: He thought his date looked great, but her dating-profile pictures must have been at least 15 years old.
People may be judgmental jerks about your appearance. But some won't be. Misrepresenting yourself, on the other hand, perturbs everyone.- Emma Witman, Bartender
Loose convictions strongly held
Potential backers appreciate the passion for a problem and the unwavering conviction that your team can build a special company. Nobody knows your business as you do. However, from time to time, you will encounter investors with a better grasp of the problem you’re trying to solve.
When you find yourself disagreeing about regulation, market data or state of technology adoption, don’t try to win the argument, turn the table.
Ask most of the questions. Learn. This is free marketing research with private data. Even if you think they’re wrong or their views are obsolete, you can find out about even more ways people have tried and failed. Indeed, that very well informed devil’s advocate may be a great sounding board for your future ideas.
Don't bring up your conspiracy theories on a first date. Just don't.
Or maybe do. They're loads of fun for me to hear.
The best so far was a guy on a first date revealing he believed that "the moon is a man-made construct" — a serious level-up from the "we faked the moon landing" theory. Not as good as the "moon is made of cheese" hypothesis though. - Emma Witman, Bartender
Small plans
The presentation starts. The team is impressive, they’ve worked together for a while, they display great rapport and coordination. The problem they’re trying to solve is big and relevant to the investment thesis, the insights are awesome, the product has potential, the deck is beautifully crafted. Traction?, yes! And then you get to their future plans. Some market expansion, some interesting product releases but nothing that shouts unicorn. Game over.
That’s how my heart gets broken every now and then. It’s hard to urge someone to be ambitious and to swing for the fences. The ‘change the world’ mantra attached to high impact entrepreneurship is definitely overused but if your first presentation doesn’t project that belief, it’s hard to sell the 10x venture upside investors need.
Assume all early stage investors are looking for the next unicorn. More, some VCs may enter the meeting thinking Latin American founders are not as ambitious as their Silicon Valley colleagues. If you’re going big, make sure your growth plans are consistent with a billion dollar valuation.
It must be a conversation
First meetings are mostly about getting to know each other. Think of them as a rehearsal of a future relationship. Rapport, intellectual connection, and a matching sense of humor are all important indicators of a potentially fun and interesting ride.
Like first dates, information needs to flow both ways. Over rehearsed monologues never work. VCs can tell when their questions are answered quickly to go back to a script. Even if the pitch goes well, entrepreneurs often leave the meeting without any new insight about the potential partner.
Much is said about great storytellers, yet great conversationalists are powerful presenters. They read the Zoom, they ask questions from the start, listen attentively, shape the presentation accordingly. They do the homework and know a lot about the firm and the people they are meeting. Most experienced founders prefer not to use a deck to make sure this happens.
It's one thing to have a back-and-forth where you've connected on deeper, emotional topics on a first date, but when it's a monologue, it's like watching a therapy session — a really awkward therapy session. - Emma Witman, Bartender
What’s next
When the financing topic comes up, the dance starts. After all, investors get paid for doing this well. They like nothing more than re-designing an investment round as if they were redecorating their home office with new gadgets and improved background. It’s key to their know-how and the reason you’re meeting.
It’s rare to find a team that has a clear financing plan for the future including the different sets of options. You know the start of the alphabet but do you understand what’s the sequence of going from zero to IPO.
The most confident entrepreneurs are very explicit about this. Make sure to understand the role of a lead investor versus a follower, the balance between investors’ expertise. Have a complete understanding of how most VCs work. Be clear about the timing of your round. Show who’s driving.
How do you know you turned off investors? People check out or get impatient, they may start to smile more or have a lost gaze. If you’re pitching online, that means they may have switched to a different screen. If this happens, you can still pull it off by emphasizing a section of your story, asking questions or cracking a joke.
If things get tense and it’s an important VC for your company. Pause. Try to reboot the meeting by acknowledging the tension or your nervousness. Start over. After all, there is more money than amazing teams with big plans. You got this.
The good news is that finding that companion of your life’s most important project often happens without too much strategizing. Just like that, even if you suck at pitching.
It happened to me in the spring 2000.
I parked my car. My decorative plastic yellow chicken claw hanging on the rearview mirror oscillated slowly. I grabbed my flip phone and step out of the car not before joining Dave Matthews for one more chorus: ♪ ♫ it’s crazy I’m thinking ♪ ♫ just knowing that the world is round ♩ ♬
My boss had to insist on my taking this meeting. “Trust me, Cecile is great!,” he said. I was honestly tired of trying to collaborate with other sinking startups desperate for traction, media coverage, and, yes, hope. After the Internet bubble burst a few months back, these partnerships felt more like a support group than the tech movement I had united.
Upon entering Il Fornaio, guests had a full view of a beautiful set of tables surrounded by plants and lit by warm sunlight transformed into a perfect Italian movie scene by the glass ceiling. At the corner of the salon, a beautiful girl sat reading the menu. As I came down the stairs awkwardly chasing my bright green New Balance sneakers, she raised her head. Her charming smile dashed all the universe’s light straight into my eyes.
My linguini was already too cold to eat when I laughed so bad I thought I had messed up yet another date. Relax, this is a business lunch, I had to remind myself. Cecile was laughing too. So we kept on smiling, for a while, in sync.
Two weeks later, as our startups inescapably sank, I proposed. Two decades since, her smile still shines high over me, while I awkwardly chase the future.
Thank you Tom, Charlene, Will, Patrick, Nick, Mohammed, Matt, Justin, Brett and Ben of On Deck OWD1 team bravo for the ideas, edits & encouragements to write this piece.
Quotes by Emma Witman from her article in Business Insider: I'm a bartender who's witnessed countless first dates — here are all the things you're doing wrong (May 23, 2019).