Tracy Chadwell of 1843 Capital explains the 'skill set of the ask'

Investing is as much a personal journey as a financial one. And like any journey, it certainly helps to know your destination before you set out.

That’s why Tracy Chadwell, founder of 1843 Capital, always asks new investors, “What are your goals?” If they’re chasing above-market returns, she points them in the direction of contributing to a new fund from a VC firm you believe in. If they prefer to go the angel route, she encourages them to spread their checks, as 90% of seed stage companies fail.

With her own firm, Chadwell invests in Series A and B companies, since she believes that stage exists at the intersection of reduced risk and significant upside. That kind of growth equity requires bigger checks to buy into companies with more traction, but it allows her to leverage her expertise. It’s a personal decision.

We asked her how she decided to target this range (and what she thinks of new categories like “super seed” and “seed extension”) on the final episode of this pilot season of “Off the Sidelines” — an investor education podcast produced by us at Technical.ly in partnership with Project Entrepreneur, a program by UBS.

Project Entrepreneur helps female founders with a targeted focus on investment readiness and building bridges to funders. By diversifying the pipeline of investors and supporters, Project Entrepreneur aims to accelerate their growth through increasing access to capital and building ecosystems to advance women entrepreneurs. Similarly, 1843 provides resources and advice to its portfolio companies, drawing on Chadwell and her team’s experience and networks.

One of the main lessons Chadwell imparts is her “skill set of the ask” — how to best prepare for making an ask, whether it’s for investment, a raise, a job opportunity or any time you’re putting yourself out there. This approach can do a lot to reduce nerves and fear, transforming a conventionally “soft skill” into a practicable technique. If you’ve ever had to make a big ask (or are planning to in the future), you’ll want to find out her “three knows to a yes.”

Listen to the episode below to hear our conversation with Chadwell, including how to master that “skill set of the ask” and what she thinks are the biggest investment red flags to avoid.

Off the Sidelines — Ep 10 — Tracy Chadwell of 1843 Capital

Check out the rest of this season of “Off the Sidelines” for more conversations with notable figures throughout the investing world. Click below to subscribe and listen to all 10 episodes.

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