Brian Hamilton built and sold two companies and has spent 34 years teaching people in prison to start businesses. Build yours alongside Catholic founders: join.catholicfounders.com (http://join.catholicfounders.com)

Brian is the founder of Inmates to Entrepreneurs and the Brian Hamilton Foundation, and he sold Sageworks in 2018. He's also brutally honest: his delivery is "way more like Steve Jobs than Mother Teresa." Silas asks him whether a tough boss can be Christlike, why he sees a real conflict between institutional capital and faith, and whether he regrets selling.

In this episode:

• Why high standards and forgiveness have to go together

• From "I don't careist" to faith, through a Baptist minister and the death of his wife

• How Inmates to Entrepreneurs teaches people to start businesses with less than $500

• Secular capital vs. an otherworldly view, and why money is a byproduct

• "I feel like I sold my family": the cost of selling your company

• Poverty, a chip on your shoulder, and letting God use it

Core lesson: Be tough, but get your heart right first. If people know you care about them, they'll forgive a lot.

Guest links:

Inmates to Entrepreneurs: inmatestoentrepreneurs.org (http://inmatestoentrepreneurs.org)

Brian Hamilton Foundation: brianhamilton.org (http://brianhamilton.org)

Starter U: starteru.org (http://starteru.org)

Chapters:

00:26 – He built and sold two companies and helped ex-convicts get work: what has he learned about forgiveness?

03:10 – In tech there are very few winners, so you have to be tough, and still leave room for forgiveness

04:28 – Raised Catholic, an "I don't careist" in college, and the Baptist minister who reintroduced him to Christ

07:41 – His wife's sudden death in 2013, and how God "crushed" him back toward Christ

14:48 – Cardinal O'Connor's challenge: "We don't read the New Testament"

16:36 – Softening hearts: "We don't change anybody." People have to come in ready

18:46 – How Inmates to Entrepreneurs works: low-capital service businesses started with less than $500

19:49 – The 1992 prison conversation ("I'm going to go get a job") that sparked the program

22:40 – Can you build a company the hard way and still be Christlike?

24:56 – Steve Jobs, VC-scale companies, and leaders who call people out of themselves

30:20 – The real conflict between entrepreneurship and faith: a secular worldview vs. an otherworldly one in institutional capital

32:21 – Money is a byproduct: focus on hitting the ball, not the scoreboard

34:14 – Starting Sageworks: the profit motive, a target number, and leading with the mission

41:29 – Capitalism, Adam Smith, and why free enterprise needs moral people

43:24 – Does he regret selling his companies? "I feel like I sold my family"

46:45 – Employee ownership trusts and preparing heirs: can you lock in a culture after you leave?

49:16 – Growing up on food stamps, and why "poverty is a social disease"

1:00:03 – The one part of the faith founders most need: love your neighbor, and persistence

1:01:12 – Stubbornness or discernment? How he decides when to keep going vs. give up

1:03:08 – Closing and Rapid Fire

Join the Catholic Founders Guild ($10/month or $100/year): grow your business, learn the theology of entrepreneurship, and meet 200+ Catholic founders. join.catholicfounders.com (http://join.catholicfounders.com)

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