#41. Hundreds of Rejections Before His First Investor | The Truth About Raising Startup Capital – Matt Buder Shapiro episode artwork

EPISODE · Mar 10, 2026 · 58 MIN

#41. Hundreds of Rejections Before His First Investor | The Truth About Raising Startup Capital – Matt Buder Shapiro

from Love in the Land with Austin Love · host Austin Love

Episode #41 – Matt Buder ShapiroHow many “no’s” does it take before you finally hear yes?For Matt Buder Shapiro, the answer was hundreds.Matt is the founder of MedPilot, a healthcare technology startup that was eventually acquired by Vytalize Health. Today he serves as Senior Advisor of Marketing & Policy at Vytalize, a company that supports more than 3,000 primary care providers and manages over $3 billion in medical spending. In addition to his work in healthcare, Matt is an active startup investor, backing companies such as Headway, Goodles, and Olipop, along with dozens of other emerging businesses.But before the growth, the acquisition, and the success… there were constant rejections from investors.In this episode of Love in the Land, Matt sits down with Austin Love to talk about what it really takes to build a company from scratch, the brutal reality of raising startup capital, and why rejection might be one of the most valuable tools an entrepreneur can have.Matt also reflects on growing up in Cleveland and his years in Shaker Heights and shares what Machine Gun Kelly was really like in high school. Topics we explore in this episode include:• The reality of raising venture capital• Why most founders hear “no” hundreds of times before a “yes”• How rejection can become fuel for entrepreneurs• Lessons from scaling one of the fastest-growing healthcare companies in America• What Matt looks for when investing in startups• The future of startups and innovation in ClevelandFollow Matt on Instagram: @mbudershapiroIf you enjoyed this episode, be sure to like, share, and follow the Love in the Land podcast for more conversations with entrepreneurs, creators, and leaders shaping Cleveland and beyond.Follow Austin on Instagram: @austinlovetv.

Episode metadata supplied by the publisher feed · Published Mar 10, 2026

Embed this episode

Ready to play

#41. Hundreds of Rejections Before His First Investor | The Truth About Raising Startup Capital – Matt Buder Shapiro

0:00 58:09

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Love in the Land with Austin Love?

This episode is 58 minutes long.

When was this Love in the Land with Austin Love episode published?

This episode was published on March 10, 2026.

Can I download this Love in the Land with Austin Love episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!