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How To Meet The Person Behind The Pitch Deck: Investor Shares Lessons From Pro Sports Career And Life

Illustration of conversation bubbles.

By Michael Redd 

Investors have an ethical responsibility to take care of their entrepreneurs, period. But research also shows that when VCs pay attention to founders, the company is more likely to experiment, innovate and be successful. Investors therefore have to make an active effort to really know who their founders are and how they are doing.

Ironically, one of the biggest obstacles to these insights is the pitch deck.

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Founders can easily hide behind presentations, and “perform” for investors, rather than reveal themselves out of fear of losing a deal. It’s up to investors, then, to peer behind the curtain and get to grips with the person beyond their work persona.

With that in mind, here are three techniques my team uses to get to the core of founders:

Play games together

Michael Redd, co-founder and chairman of 22 Ventures

I started my professional sports career in 2000, and every time I finished a game I walked away knowing a little more about my teammates—even the ones I’d played with for years. It’s the same with founders: if you want to peel back the layers, put them in a game setting.

Basketball coach John Wooden famously said that “sports don’t build character, they reveal it.” Sports show how people deal with adversity, if they’re humble when they win, and if they’re resilient when they lose.

Sports also show people’s sportsmanship: if they play fair, to whom they attribute losses to, and how they help others who may be struggling.

In the past, we’ve invited founders to play a friendly game of pick-up basketball. People are always more themselves on a court than they are in a meeting—the competition brings out their true colors.

In some cases, we’ve seen people flip a switch mid-game and have decided not to work with them because they’ve made it clear that they’re not a team player.

That’s not to say that investors should be testing founders’ physical abilities. A game doesn’t have to be intense exercise, it could also be a board game or video game.

You’re not trying to trick founders, either. Instead, you’re giving them the opportunity to express skills that investors otherwise might not see: how they develop strategies, problem-solve, communicate and hold their general composure.

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Ask open-ended questions

We ask leading questions far more often than we realize. For investors, it’s normally because we want a concise “yes” or “no” answer that will save us time. But when getting to know someone, you need unprompted, qualitative information that provides a more complete view of their world, their priorities and how they think.

Questions like “What things energize you?” and “Who have been your favorite leaders and why?” give founders the freedom to answer in as much detail as they like.

It also gives them the autonomy and space to be as vulnerable as they’re comfortable with. Some will share a personal story, others will refer to Forbes‘ list of inspirational entrepreneurs. There’s no right or wrong answer, but it tells investors what the driving forces are for the founder.

Open-ended questions should also offer insights into the founder beyond the pitch deck. At 22 Ventures, we don’t follow up pitching sessions with projections and metrics; we ask about the founder’s family, their most recent vacation, the book they’ve just finished. These questions help tease out a founder’s personality, interpersonal skills, values and interests beyond the job—something you only tap into if they feel comfortable in conversation.

Overshare with founders

As humans, we shy away from the idea of oversharing because we assume it means making ourselves or someone else uncomfortable. For investors, oversharing means broaching subjects with founders that are traditionally avoided in introductions, but that’s not a bad thing.

If you want to really get to know someone, you can’t get stuck on small talk and formalities. It’s even been proven in dating: A study found 80 percent of participants preferred to date people who revealed things rather than hid them, even if the revelation didn’t paint them in the best light.

Tell founders early on if you’re taking (or have taken) coaching sessions, if you struggle to balance work and home life or if a relative is getting married. When you share these snippets of your life, watch how founders react, and give them the time to reciprocally share.

By opening these doors, you not only discover what’s happening in each other’s lives, but you can also align and connect around the experiences. For example, you could recommend coaches and healthmcare professionals to founders, or remember important events for their loved ones and check-in when those dates arrive.

Of course, you shouldn’t pressure founders to share personal issues. The idea is to bring down barriers and create an environment where founders feel free to tell you as much or as little as they want.

Entrepreneur Marcus Lemonis said “the idea that business isn’t personal is total BS.” Business is people and therefore always personal, and investors have a responsibility to really know their founders before jumping into a partnership.

By pulling the person out of the pitch deck, investors can build those genuinely compatible relationships from Day One.

 Michael Redd spent 12 seasons playing in the NBA and on the U.S. Olympic team. He is now co-founder and chairman of 22 Ventures, the angel firm investing in people—not profits—by offering valuable connections, entrepreneurial experience and genuine concern for founder well-being.

Illustration: Dom Guzman

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