Forty Years of Starting Over: A Fireside for Bloomington Business Owners

Thursday, October 29th, 2026 at 4:30 PM
229 S Grant St Suite 1, Bloomington, IN 47401Bloomington, IN

About This Event

OWN MEMBERS GET IN FREE. AT CHECKOUT, ENTER THE EMAIL ADDRESS TIED TO YOUR OWN MEMBERSHIP AS THE PROMO CODE.

Bill Black started his first business at sixteen washing airplanes. He worked out pretty quickly that he could not make much money as the only person holding a bucket, so he hired a kid down the road who rode his bike up to help.

That was the first of a lot of them. Gas pump repair in the late eighties turned into point-of-sale work, which turned into computers. A good corporate job in Madison paid the bills and made him want out of it. He and his wife bought a restaurant to create a path to get out of the corporate world. As the profits and savings dwindled, they doubled down and rented space to start a second one, structured a little differently. It took two years to go through their entire life savings. The IT company that finally worked ran eighteen years before he sold it in 2012.

He started his current company three months after that sale and still runs it today. Forty years in, he is in the middle of another pivot.

If you have been running the same business for twenty years and you are quietly wondering what the next chapter looks like, this one is for you.

The businesses, in order

  • Airplane detailing
  • A tanning salon, a side hustle with family
  • Two restaurants
  • Mobile computer repair
  • An IT services company out of North Vernon, run 18 years and sold in 2012
  • An online store, on the side
  • FocusPlanit, his current company

What we'll get into

  • Hiring his first employee as a teenager, because working harder was not going to be enough
  • Buying a business to get out of a job, and what that actually took
  • Quitting a steady job on a verbal promise, and what he would want in writing today
  • The ceiling most owners never get past, and how he decided selling was the right move
  • Knowing when to sell and when to dig in
  • What is changing in his business right now and what he is doing about it

Who should be in the room

This one is built for people who own or run a business, or are working to. Owner-operators, family businesses, people who bought something they now run themselves, and people building something new that would never call itself a startup.

If you sell to owners for a living, come as an OWN member. We keep these rooms operator-heavy on purpose, because that is the only reason anybody says anything honest.

Our first night in Bloomington

We have done Carmel, Fishers, Indianapolis, Syracuse and Fort Wayne this year. Monroe County has been on the list since we started, and we are glad the first one is with somebody who lives here. If you know a Bloomington owner who belongs in this room, forward this to them. That is how these fill.

How the night runs

4:30 to 5:30. Doors, drinks, and networking.

5:30 to 6:30. The conversation, plus your questions.

6:30 to 7:30. More networking.

Hosted at BRU Burger Bar, 229 S Grant St, at the corner of Grant and 3rd near the IU campus.

Your ticket

General admission is $15 and includes food and drinks. OWN members attend free. Enter the email tied to your OWN membership as the promo code at checkout and your ticket is comped.

About Bill Black

Bill lives in Bloomington and has started eight businesses and side hustles over four decades. Before going out on his own, he ran IT infrastructure for a Madison manufacturer with operations in the U.S., Canada and Mexico, including a 24/7 support center. After selling his IT company in 2012, he started FocusPlanit, which has helped hundreds of IT service companies get their operations, sales and finance in order. He runs a monthly webinar for owners in that industry and writes a newsletter on building the structure a growing business needs. His rule for owners: "You are not the business. The business is the team doing the work."

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