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Matt began as a top consultant at McKinsey, where he witnessed the power of customer loyalty programs and immediately understood why large companies pay millions of dollars to create them. His vision for Fivestars was to make the power of a Fortune 500 customer loyalty program accessible to local businesses. Fivestars has gone from two guys in a garage to serving thousands of businesses across the country. In October 2021, Fivestars was acquired by global payments leader, SumUp.

Matt has led technology at FiveStars since its founding, spearheaded their transformation into a payments company, and drives ongoing business development and payments strategy. Before Fivestars, he volunteered with TechnoServe in Uganda, was a strategy consultant at McKinsey & Company, and an analyst at AVM, a 32-year-old global macro hedge fund.

On this episode, Chris & Matt discuss:

➡️ Their process for deciding what startup idea to pursue & why they chose a loyalty program for small businesses

➡️ Lessons learned while building a startup

➡️ The challenge of finding product market fit, even if the business is growing like a rocket ship

➡️ How AI will impact businesses and consumers

Timestamps

(00:03:00) From El Paso to the Tech world

(00:09:26) What does an entry-level person at McKinsey even do?

(00:11:17) Did you have a filter for easy no’s while in consulting?

(00:12:48) What’s an example prototype you were working on in Technology?

(00:15:07) How did you transform your skillsets to become a CTO?

(00:17:10) What did you get from Y Combinator and learn from Paul Graham?

(00:19:46) What was the origin of Fivetars?

(00:24:42) If you were building another company now is there a way to avoid the mistakes you made the first time?

(00:26:09) Finding Product Market Fit

(00:30:06) How do you avoid the trap of taking on too much overhead?

(00:36:13) How were you able to take the credit card fee and turn it into more CRM users?

(00:38:56) When did you begin to decide it was time to sell?

(00:43:10) What was the transition like going from start-up culture to integrating into a larger organization?

(00:47:32) How are you receiving the entrance of AI?

(00:50:29) Will the job of the VC change with AI?

(00:52:48) How Chris thinks AI will affect RE

(00:58:49) How should we simplify all of these different AI languages available?

(01:01:44) How is the American Customer right now?

(01:05:18) What are you predicting for the Startup scene over the next five years?

Additional Resources

👉 Fivestars

👉 Matt on LinkedIn

👉 [email protected]

➡️ Fort Capital: www.FortCapitalLP.com

➡️ Follow Fort Capital on LinkedIn: www.linkedin.com/company/fort-capital/

➡️ Follow Chris on Twitter: www.twitter.com/FortWorthChris

➡️ Follow Chris on LinkedIn: www.linkedin.com/in/chrispowersjr/

➡️ Sign Up for our Newsletter: https://newsletter.thefortpod.com/

➡️ Subscribe to The FORT on YouTube

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The FORT Podcast with Chris Powers is a place where you can find meaningful conversations about entrepreneurship, real estate, investing, and more.

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