Twenty Years In, Two Years for Me

This is the 20th year of Okoboji Entrepreneurial Institute (OEI).

It's only my second.

Sunday night I sat in what used to be Tom Bedell's home — a legacy among legacies. As legend has it, Tom's late father, Berkley Bedell, got his start while still in high school. Around 1937, Berkley began tying fishing flies with $50 he'd earned from his newspaper route, some dog hair and feathers from some backyard chickens, then sold them to a local tackle shop in the Iowa Great Lakes region to local and visiting anglers.

With his family's encouragement and his own entrepreneurial instincts, he built what became Berkley + Co.

Main Room at Peace Harbor where businessowners, coaches and investors welcome the 2026 OEI class.

His son, Tom Bedell, didn't fall far from the tree. Tom loved music and by sixteen he'd started his own company, Bedell Guitar Company (and later Breedlove). Tom has been a passionate advocate for sustainable practices in acoustic guitar manufacturing — one of the many reasons I've enjoyed learning about this family's business over the years.

Tom eventually took over his father's business, Berkley + Co., as president, and sold it in 2007.

But, he didn't stop there. He went on to follow his own passions alongside his wife, Molly, started a new venture in the music industry, and has recently begun his retirement. He sold the record-breaking Iowa home not long ago, and the new owners have opened it up to nights like this one — which struck me as its own quiet kindness, choosing to carry a legacy forward instead of closing the door on it.

I go into weeks like this with feelings that don't resolve cleanly. The world has changed fast since COVID, and it's changing fast again with AI. I look at what people build — the ingenuity, the creative ways they find to reduce suffering — and I find it genuinely spectacular. Then I sit at a table with more wealth in the room than I'll ever hold, and something in me pulls in two directions at once.

I don't say that to knock the people who built it. Most of them started with nothing and worked for every bit of what they have. I say it because I think it's the same tension a lot of the students, and many others of us, in this room are carrying, even if they don't have words for it yet:

How do you want your own place in the world, while also wanting to be useful in it?

How do you sit next to opulence and still believe your own contribution matters?

I don't have a clean answer.

I have a practice instead.

Last night as I walked in, nervously scanning the room for a face I recognized, I saw my friend Helen, from church, talking among some of the students from this newest class at OEI. She's the kind of person who works a room like it's second nature — moving from story to story, making sure everyone feels like they're part of something. She pulled me in. She made sure I wasn't ever standing alone. And what I noticed, watching her do that for other people too, is how simple the thing underneath it actually is.

Everyone in that room wanted the same thing: to be seen. To be included.

To have someone reflect their story back to them like it mattered. Helen is the kind of person that just does that. She embodies it, quietly, effortlessly and kindly.

My friend Helen and I in the Irish Pub at Peace Harbor

I also ran into my old friend, Lance, from years back, working the bar with his two daughters (Pictured below, without Lance, because true to form he was running about serving everyone). He's worked this event for something like 18 years now, with little recognition for it — showing up every year, doing the hard, unglamorous work of serving everyone else, and doing it with a smile. I thought about that for a while afterward.

The people two seats from a multimillionaire, and the people quietly keeping the whole night running, both matter. Both are part of what makes a week like this actually work.

That's what I want to bring into my coaching sessions this week.

Not my stories. Theirs.

My job isn't to hand these students my goals or my path. It's to be a mirror — to listen for what they're actually building and reflect it back clearly enough that they can hear it themselves.

Are they proud of what they're doing? Are they pushing past something that scares them? Are they helping someone else take a step up, or just trying to get ahead of them?

Those are the questions that matter to me, in business and out of it.

I don't fully know why I keep getting invited back to a table like this. I'm not the multimillionaire two seats over with a lifetime of advice to hand out.

But I've decided that what I bring — the listening, the reflecting, the willingness to sit in the discomfort of not having it all figured out — is worth just as much as anyone else.

Different tools. Same table.

Twenty years of OEI. My second year in it. Eyes wider open than last year, heart more open too. I'm grateful to be here, grateful to be trusted with these stories for a week, and honestly still a little in awe that I get to be. 💓 This week, I'll spend some time "coaching," though truthfully, I learn more about myself and what I want out of my own life than I feel I'm actually helping the students. I'll share some of those stories later this week. In the meantime, you can look back at my time here last year in the blog links below.

Disclosure: Iowa Lakes Corridor is a client of Vertical Marketing + Design.