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Main Street Minute

Every Biz Buyer Must Think About This

April 16, 2025
3 min read
Hey Biz Buyers,

Welcome to Main Street Minute — your inside line on our community of people working to buy and scale small businesses that actually cash flow.

Each week, we open the doors to more business buyers, operators, and builders. Some of the latest to walk in?

  • A finance pro at a major healthcare company
  • A marketing agency owner
  • A financial analyst for the US Army
  • A specialized mental health therapist
  • An IT business consultant

Now, onto the big idea this week…

Investing in the businesses that power your business.

You don’t need a corporate M&A team or billions in dry powder to do it. We’re doing it right now in our community. In this week’s breakdown, we’ll show you:

✅ The exact 3-step playbook we use

✅ A real-world example from inside our own portfolio

Let’s break it down…

Owner Framework

The Power Stack Method

This is one of the top growth strategies we see big businesses using. Stack solutions that power your business — and own them. But few small business owners realize they can actually do it, too.

The idea is simple: Invest in the businesses that power your business. Here’s an example from our portfolio:

Core business: Contrarian Community 😉

What does this business do? An educational community to help people own & scale small businesses through acquisitions.

Great. But here’s the thing with folks in our community…

  • Many are already running a business
  • Many are working high-pressure W2 jobs
  • Some are doing both
  • On top of deal searching, parenting, etc…

They don’t have time to seek out the best resources, vendors, and systems. That’s the point of our community — to cut the noise. So that’s where our other investments can come in.

  • Step 1: Serve small business buyers & owners
  • Step 2: Invest in companies that solve SMB tech pain points via our VC fund, Contrarian Thinking Capital
  • Step 3: Integrate those solutions in the community to make our members’ lives easier

Example: Doola.

They offer a business-in-a-box service that does it all from formation to tax filing to bookkeeping & more.

We built a Slack channel to give our members access to Doola’s reps & get business questions answered more easily and quickly. Here’s how it looks…

1. The Expert Call

Doola hosts a high-value presentation on how entrepreneurs can save on taxes.

Doola gets to show off what they know best, and how they can best help, our members get the help they need. Win-win.

Slack message promoting a tax-saving webinar for entrepreneurs with tips on compliance, efficiency, and real-time Q&A

2. Slack Integration

Members post their Qs, any time. A Doola rep swoops in with the As. Win-win.

3. Concierge Customer Service

People don’t want a generic FAQ page. They don’t want to spend hours tracking down the right person who can help, either. People just want to ask their specific question & get their specific problem solved. They want personalized, high touch, and easy access.

So we built out this kind of solution:

Slack conversation where a user asks for help updating an old LLC, with a support reply including a help link.

It’s a playbook that Amazon, Google, and others follow, though we’re doing it at a much smaller scale:

  • Build a core business.
  • Buy or invest in companies that improve the experience & value of the core business.

Some call it “synergy.” We call it common sense.

Scenes from our Contrarian Community
Contrarian Community pictures
Team Contrarian

The information contained here may not be typical and does not guarantee returns. Background, education, effort, and application will affect your experience. Your results will likely vary.

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