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In Today’s Issue:
Intro to the Guest and Topic
Core Takeaway
Episode References
Select Quotes
Key Moments
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Today’s Topic & Guest:
Brian Hamilton | Inmates to Entrepreneurs & Brian Hamilton Foundation
Brian Hamilton has built and sold two companies, including Sageworks, the fintech company he sold in 2018. Before that, in his 20s he ran a chain of inner-city coin laundromats. And since 1992 he’s been going into prisons to teach inmates how to start a business, because it’s hard to get a job with a record.
That idea became Inmates to Entrepreneurs. By Brian’s count, 7 out of every 10 people who come through the program graduate, and about half of those start businesses. Low-capital service businesses: washing windows, cutting lawns, painting. Businesses that take less than $500 to get started.
Brian was a lot of fun to speak with. In part, because he’s brutally honest. And he wrestles out loud with a question every serious founder should ask: can you build a company the hard way and still be Christlike? Should I have sold my company? Etc.
Of note, we spent a good amount of time discussing the conflict between institutional capital and faith.
Please share your favorite takeaway in the comments!
Quick note, if you are listening with small children some of the following content may not be suitable for young ears.
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Core Lesson:
You Can be Tough and Charitable.
Brian was very candid about the fact that he’s a hard person. We talked about Steve Jobs and his reputation as well. Founders who push people hard and are often considered hard, tough, or just rude.
Brian argues that some of these companies require people like that to make them work. A lot of companies required gargantuan effort to get to a point of actually working and running on their own. Getting there can lead to hurt feelings.
But, there is a way to stay charitable to the team while still pushing people.
We kind of settled on the idea that as a leader, you need to push people to do their best work. Still show care and treat them like humans who deserve respect and dignity. But you can be hard and push aggressively.
After all, there are some companies that won’t make it if you don’t do this. If you are too soft, the entire company may end up failing. That would lead to some even harsher realities that each family has to face.
To summarize, you can drive hard and call people to their best work, but you need to recognize the need to still treat people with charity. Many people are looking to be called to a mission. They want to do something big. You can call them to that. Just keep their infinite human dignity at the front of your mind.
God Bless & Happy Building!
~Silas Mähner
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In LatAm and the Philippines, there are millions of Catholic remote workers (across all domains) who want to work for ethical bosses.
Often, they’re treated as second-class citizens or work for organizations that ask them to do questionable things. They reach out to us in search of a Catholic boss.
So, we started ParacleteVA (website coming soon).
With ParacleteVA, we’ll find you vetted, Catholic overseas talent who will help you move your business forward.
How it works: Pay a $500 finders fee when the candidate starts and $500 if you’re still happy with them after 30 days.
To get started, reach out to catholicfounders@gmail.com with what you’re looking for, and we’ll get started.
Key Episode References:
Inmates to Entrepreneurs (founded 1992) and its free course, Starter U
“Shall we persist in sin that grace may abound?” (Romans 6:1)
“Stop judging, that you may not be judged” (Matthew 7:1), his rapid-fire scripture
The greatest commandment, when the Pharisees test Jesus (Matthew 22:34-40)
Rev. Robert Harris, the Baptist minister who started the prison ministry with Brian, and Cardinal O’Connor’s talk at his college
Adam Smith, The Theory of Moral Sentiments and The Wealth of Nations
Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families
#96 with the founders of P. Terry’s and their Employee Ownership Trust
Henry Kaestner (Faith Driven Entrepreneur)
Steve Jobs and Jony Ive; George Foreman vs. Muhammad Ali, the “Rumble in the Jungle”
Select Quotes:
“It’s not a business journey, it’s a life journey.” — Brian Hamilton
“There’s spiritual battle all the time going on. In our own hearts, right, between good and bad and our good thoughts and bad thoughts.” — Brian Hamilton
“If you care about the people and you love the people you’re serving... I know they will show you a lot of forgiveness for you. So you got to get your heart right.” — Brian Hamilton
“We teach people how to fish and we teach people how to start their own low capital service business.” — Brian Hamilton
“The money is a by-product. It’s like playing tennis, right? We focused on hitting the ball, not the scoreboard.” — Brian Hamilton
“You got to give that to God. It’s too big.” — Rev. Robert Harris, as Brian recalls it
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Key Moments: (outline)
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
Hire Catholic Overseas Talent
In LatAm and the Philippines, there are millions of Catholic remote workers (across all domains) who want to work for ethical bosses.
Often, they’re treated as second-class citizens or work for organizations that ask them to do questionable things. They reach out to us in search of a Catholic boss.
So, we started ParacleteVA (website coming soon).
With ParacleteVA, we’ll find you vetted, Catholic overseas talent who will help you move your business forward.
How it works: Pay a $500 finders fee when the candidate starts, and $500 if you’re still happy with them after 30 days.
To get started, reach out to catholicfounders@gmail.com with what you’re looking for, and we’ll get started.
