What can investors learn from entrepreneurs? - Technical.ly


Oct. 26, 2020 12:53 pm

What can investors learn from entrepreneurs?

The new episode of investor education podcast Off the Sidelines features two founders-turned-funders, plus NPR’s Guy Raz.
(L to R) McKeever Conwell, Emily Foote and Guy Raz.

(L to R) McKeever Conwell, Emily Foote and Guy Raz.

(Technical.ly file image)

The trope goes that the entrepreneur mired in the messy details of executing their vision must seek counsel from the wise investor-adviser. The investor who has seen many deals across many industries offers insight.

Though this dynamic does play itself out, it misses an important part of the puzzle: what and when entrepreneurs can teach investors. It’s true that new companies following a well-trodden path and aging companies fulfilling familiar growth patterns are well suited to the cold, calculating stare of finance wonks. But if you believe there just may be art remaining in entrepreneurship, then those who have led through the messy, human journey have something to share.

Some entrepreneurs, and early employees, take their winnings to the investment side. But many active investors come from industry experience, finance expertise and other business expertise outside of the stage they’re investing in. What can investors learn from entrepreneurs that they can take into their own practice, whether or not they’ve done their own company founding?


That’s the focus of the second episode of the second season of Off the Sidelines, an investor education podcast produced by us at Technical.ly and sponsored by Project Entrepreneur, a program by UBS.

Project Entrepreneur focuses on investment readiness and building bridges to funders, with the goal of improving enabling environments for women founders and advancing inclusive capital, so we partnered to produce this series exploring trends in business investment.

In this episode, we gathered perspectives from two VCs who traveled that founder-to-funder journey — Emily Foote, principal at Osage Venture Partners, and McKeever Conwell, founder and managing partner at RareBreed Ventures — as well as insights from entrepreneurship expert Guy Raz, host of NPR’s popular podcast “How I Built This.”

Check it out for their thoughts on the need to be honest and authentic right from the start of a business relationship, how to sync up when goals are different and how listening to entrepreneurs with diverse backgrounds can open up new market opportunities.


We have more episodes coming up this season with conversations from notable figures throughout the investing world, so be sure to subscribe and keep up to date with all our episodes.

Follow Off the Sidelines here

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