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Into the mind of a successful entrepreneur

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Jeremy Berman  (left) interviews John Osborne of The Harbor Entrepreneur Center during a recent Startup Grind. (Photo/Thomas Heath)

I’m an entrepreneurial geek.

There, I’ve said it. In writing, no less. I can’t take it back. Some people are food geeks. Others are gadget geeks. Still others, musical theater geeks. For me, I’m fascinated by businesses. ... How do you start them? Grow them? Sustain them?

It was with that mindset that I set out to a recent Startup Grind meeting to hear John Osborne being interviewed by the always engaging Jeremy Berman. Osborne is one of the forces behind The Harbor Entrepreneur Center, Charleston Angel Partners and Funding Charleston.

He has built shared workspaces, launched business accelerator programs and created the recent Charleston Angel Conference, where local businesswoman Krissa Watry, of startup Dynepic, pitched her way to win a $100,000 investment.

Are you thinking what I am? “When does this man sleep?” I’m not sure he does that much.

But his wife, Allison, vouched to the audience, when called upon, that he is indeed a great husband and father (and in the end, isn’t that the most important stuff?).

Now, in keeping with my self-imposed 500-word limit, here are some of that night’s highlights from the active mind of entrepreneur John Osborne ...

“How is what you’re doing impacting your business on this day?” 

When he said that, it really made me think. Especially when it came to making daily choices on what to focus on in running a company. John talked about learning the importance of how to “be efficient and effective with time.”

On his first trip with partner Patrick Bryant to visit The Nashville Entrepreneur Center to see how those folks were running their successful hub, he didn’t care as much about the cool space and its bells and whistles. 

John wanted to know about the inspiration: “Take us back to just two dudes at a bar, and what did you do to initially get this all started?”

Talk about going to the heart of the matter.

Find your entrepreneurial peeps. To me, that’s what John was saying when he talked about getting in with a mastermind group, like his Harbor’s Forum Groups. A place he said, where “you’re not afraid to admit you’re having trouble meeting payroll and your grandmother just died.”

In other words, a safe haven to be honest and vulnerable with your fellow peers.

His best advice for startups? “Stop thinking and start doing. Just make the call. Be in more dialogue with more people. The worst thing that happens is you’ll be more educated than you were before the dialogue.”

Top mistakes on pitch decks? “Too many words, not enough data points. And ‘What’s the Ask?’”

As a coach, I couldn’t agree more. Too many budding entrepreneurs aren’t clear on what they’re asking for in a pitch.

Another tidbit: “Don’t be afraid to get into an uncomfortable position.”

How did he see his future legacy? “He had a thing that made a difference and helped some people along the way.” 

Now, to me, that’s the mindset of a successful entrepreneur. 

Thomas Heath is a business coach, strategic adviser and founder of Thomas Heath Coaching. Got a question? Planning a great startup event? He loves to respond  to our readers. Contact him at or on LinkedIn at

Startup Roundup

An insider’s view into Charleston’s Startup community. Curated by Thomas Heath.

In the venture capital world, everyone is looking for the new Google before it hits BIG. Just last year, two Holy City-based startups, SPARC and PeopleMatter, each sold handsomely (the former for $55 million). With an exploding tech and digital scene going on here, how does one keep track of it all? That’s where we come in. 

Welcome to Startup Roundup, your guide to which cool events are worth your time. How do I know? I make a living helping build Charleston’s early-stage companies. It’s my job to know what’s going on in our entrepreneurial ecosystem. Here are some of the best happenings this month:

One Million Cups
9-10 a.m. Feb. 8, 15, 22

Think of this gathering as “Shark Tank, without the Sharks.” Each Wednesday morning over coffee, all across the country (hence, the 1 million cups), a different entrepreneur pitches their company or concept to a room full of folks for supportive feedback to help grow their business. You’re bound to learn some interesting things. The Harbor Entrepreneur Center, 1505 King St. Extension. Free. Just show up (and be nice.)

The Iron Yard
6-8 p.m. Feb. 10

Ever wanted to know how to develop cool apps, but didn’t think you had the time or money to do so? That’s what Betsy Hare and her ninja team at the Charleston campus of this national software-coding academy come in. In as little as 12 weeks, someone can get up to speed as a junior developer. Refreshingly, they put special emphasis on culture, community and life balance. At this particular event, the focus is on women in tech. They’ll be hosting a screening of the documentary “CODE: Debugging the Gender Gap,” which aims to inspire change in mindsets, in the educational system, in startup culture and in the way women see themselves in the field of coding. Trident Technical College, 7000 Rivers Ave., Building 920, Room 791, North Charleston. Free. Register:

Startup Grind
6-8 p.m. Feb. 15

This global startup community is designed to educate, inspire and connect entrepreneurs. Each month at the Charleston chapter, coordinator Jeremy Berman conducts a “fireside chat” with a successful business leader who has a unique story to tell. His questions are awesome. The answers will sometimes surprise you. Launch Pad, 174 Meeting St. 2nd Floor. $10. This month’s featured speaker: Steve Lesniak, president of Celadon. Register:

Fridays at the Corridor
8:30-9:30 a.m. Feb. 17

Ernest Andrade & team have one mission: To facilitate the development of Charleston’s tech economy through adaptable office space and like-minded connections. Hundreds of successful companies have launched from here. Once a month, they bring in a great speaker on a relevant business or tech topic. Always good content! Charleston Digital Corridor, 475-A East Bay St. $25 for non-members. This month’s topic: Building An Executable Business Plan. Register by email: 

Charleston Women in Tech
11:30 a.m.-1 p.m. Feb. 23

Carolyn Finch heads up this collaborative effort of local women leaders, educators and tech professionals with a mission to support and mentor females of all ages in the technology industry. As most events I go to are more attended by the testosterone crowd, these smart ladies are a welcome relief. You have to be a member to join this event, their annual Mentor/Mentee Luncheon, so reach out to them at Charleston Southern University, 9200 University Blvd., Whitfield Center, North Charleston. Free for members.

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