How to Knock Out the What Ifs: Jenny Lefcourt Shares Lessons Learned as a Founder and Investor

How to Knock Out the What Ifs: Jenny Lefcourt Shares Lessons Learned as a Founder and Investor

How to Knock Out the What Ifs: Jenny Lefcourt Shares Lessons Learned as a Founder and Investor 1024 683 33Voices

Munjal Shah, one of my personal heroes and the Founder and CEO of Health IQ, recently shared the Godzilla problem with me. The Godzilla problem is the dreaded moment in a pitch meeting when an investor asks a founder: What if Google releases this product tomorrow?

To my naive chagrin, I’ve quickly learned that entrepreneurship is defined by ‘What-ifs?’ Whether we like it or not, uncertainty permeates each decision we make.

David Tisch, the Co-Founder of Spring and Managing Partner at BoxGroup, puts it best when he describes the reality of life as a founder.

You have to make huge bets on a daily basis without any real information about what you are supposed to do. Every single piece of it is ripe with insecurity. Your job as a founder is to fight all of that.

David Tisch on uncertainty.

I’ve spent from May 10, 2014 (graduation day) to today trying to figure out how to beat uncertainty.

While I’ve yet to find a crystal ball (I’ll let you know when I do), my conversation with Jenny Lefcourt, a Partner at Freestyle Capital, is among the most actionable I’ve had about how to KO the What-ifs.

The what-if mind racing is not productive…It doesn’t do anything constructive for you as an entrepreneur or an investor.

You have to learn how to shut that voice off. Think hard. Be smart. Be disciplined.

Jenny’s the first to admit that shutting it off is easier said than done. When it feels impossible to hit pause on the soap opera unfolding in your head, she recommends reading Tony Robbins and remembering our friend Sukhinder Singh Cassidy’s advice to “Choose possibility.”

Choosing possibility is inherently freeing. It enables us to be relentless; Not because we don’t see the obstacles in our way, we’ve simply chosen not to let them define us.

Although Sukhinder speaks on possibility in light of women in tech, a topic Jenny and I cover in her 33founders episode, the notion can be applied to every aspect of our personal and professional lives.  

It’s our natural inclination to choose possibility when we’re relentless about achieving our dreams.

Jenny attributes her early success building, an online wedding registry, to the invigorating combination of naiveté and grit that guided her after dropping out of Stanford Business School.  

“Ignorance is bliss… Just believing that I was going to move forward and knock down the barriers in front of me.  Not knowing what’s behind barrier one ends up being a blessing and gives you all the power to knock down one barrier at a time,” she shares.

The decision to focus on the road ahead, rather than the obstacles you may face, is certainly not a message for founders to be jaded about their product or the market their entering.

Deep knowledge and thoughtful preparation are vital when founders are meeting with potential investors, team members, and partners.

The most important advice Jenny shares about pitching is to pitch to your unique audience. Each customer, investor, and potential partner will have different questions about your work. Answer their questions, not every question that applies to your business.

In terms of preparation, Jenny suggests founders come equipped with an appendix. Having all of your facts and visual representations on hand allows you to seamlessly reference each topic a partner wants to discuss.

Remember that meeting one is an introduction. As a founder, you’re working to build rapport and ignite interest that will invoke action.

Fierce relentlessness is the most important quality Jenny seeks when deciding which founders to partner with.

These are the four telling characteristics she looks for when identifying a world class team.  

  1. Authenticity: Does the problem you’re solving keep you up at night?

  2. Big vision: What have you done to achieve your goal today? What milestones do you have set to make your version of the future a reality?

  3. Relentlessness: Entrepreneurship is a roller coaster with an occasionally malfunctioning seat belt. Will you be able to survive the Goliath drops?

  4. Leadership: How capable are you of inspiring people (customers, partners, team members, etc.) to do business with you?

To learn more about what Jenny looks for in her investments, as well as her journey starting three companies, tune into her episode of 33founders and follow her on Twitter here.

Here’s a glimpse of what we discuss:

  • Jenny’s experiences raising capital, including the most challenging questions she was asked as a founder
  • How to assess acquisition offers
  • How to deliver a meaningful and engaging pitch
  • How to maintain relationships with investors, including when to reach out to keep the momentum going
  • Why founders should choose realistic valuations – “Bigger isn’t better.”
  • Positive strides we can make in the gender conversation