What does it take to bootstrap a company, achieve a private equity exit, and then score a second windfall with a double exit?

In this episode of Triangle Tweener Talks, Dusan Babich shares his incredible entrepreneurial journey, starting with his move from South Africa to the Triangle in 2015 to grow Device Magic.

Dusan reflects on the lessons learned from an earlier startup failure, how those experiences shaped his approach with Device Magic, and the insights he gained during his private equity journey—including understanding the Rule of 40. He dives into the art of distribution, go-to-market strategies, and why he opted out of traditional VC funding.

But that's not all—Dusan also gives us an exciting sneak peek into his next big venture. Whether you’re a founder, aspiring entrepreneur, or just curious about what it takes to thrive in the startup world, this episode is packed with actionable advice and inspiration.

Tune in to hear:

• How Dusan turned a failure into a foundation for success
• His decision-making process behind skipping VC funding
• The inside scoop on selling to private equity and the power of the double exit
• Founder tips on distribution and go-to-market strategy
• A preview of what’s next for Dusan Babich

Where to Find Dusan Babich:

• Linkedin: https://www.linkedin.com/in/dusanbabich/
• X: https://x.com/dusanbabich
• Instagram: https://www.instagram.com/dusanbabich

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

(00:03:17) From Mechanical Engineering to Tech Entrepreneurship

(00:08:39) "It was also not a very fun product in the sense that there was no creativity."

(00:10:35) Relocating for Better Business Opportunities in Tech - "I had promised myself not to try and scale another software business in South Africa."

(00:16:22) Lessons learned from Device Magic + Bootstrapping
(00:18:11) How Dusan exited Device Magic, and then, the Double Exit

(00:29:30) Transitioning from Entrepreneur to Angel Investor

(00:32:11) Building Something New in AI - "It's a crazy space, but it's nice to be building something again."

(00:40:00) Scot's AI Journey

(00:49:00) Lessons to Dusan's 22-year-old Self

Referenced:

• How two South African schoolmates launched a Raleigh-based tech company: https://wraltechwire.com/2019/02/13/how-two-south-african-schoolmates-launched-a-raleigh-based-tech-company/
• How a Raleigh startup has maintained its company culture amid rapid growth: https://wraltechwire.com/2019/04/17/how-a-raleigh-startup-has-maintained-its-company-culture-amid-rapid-growth/
• Dusan on Entrepreneurs on Fire Podcast: https://www.eofire.com/podcast/dusanbabich/

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.

Throughout her corporate consulting career in the 1980's, Robbie Hardy continued to rise in the ranks.

However, according to Robbie, "I kept thinking there had to be something more. I was the always the only woman in the room, but I kind of didn't know that was weird because I didn't know anything else."

So in 1993, Robbie founded her first company - and then sold it two years later.

She's an entrepreneur through and through, and she's passionate about helping women invest in women.

Today, we hear her story, including a sneak peek of her next book!

Where to Find Robbie Hardy:

• Linkedin: https://www.linkedin.com/in/robbiehardy/
• Instagram: https://www.instagram.com/robbiehardydotcom
• RobbieHardy.com

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

(00:02:30) Why Robbie never graduated from college

(00:05:50) The idea - and why Robbie bootstrapped her first company

(00:12:00) Building to 25 people and getting acquired

(00:17:00) What happened after the acquisition (it was a lot of meetings)

(00:22:00) Starting to angel invest in 1995, and running an investment group

(00:37:45) A Million Dreams Across America

(00:48:00) Moving to Hawaii

(00:54:00) Writing her books, plus an exclusive sneak peek into the next book

(01:01:00) Starting xElle Ventures

(01:23:00) Entrepreneur in Residence at Duke University

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.

In 2005, Jesse Lipson founded ShareFile, which he bootstrapped until it was sold to Citrix Systems in 2011 - for $93M.

So how did he do it?

And what inspired him to start Raleigh Founded coworking and his latest venture Levitate?

Let's find out on today's Triangle Tweener Talks!

Where to Find Jesse Lipson:

• Linkedin: https://www.linkedin.com/in/jesse-lipson-625195
• X: https://x.com/jesselipson
• Levitate: https://www.levitate.ai/

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

(00:02:30) Does a Philosophy Degree help with entrepreneurship?

(00:06:20) Jess gets caught up in the dot-com boom

(00:09:00) An email signature idea that didn't work out

(00:13:20) The origin of ShareFile, and the origin of a power couple

(00:22:30) Testing Google AdWords - and then spending $300K/mo

(00:29:05) How many dials does it take to book a demo? What's the show rate on the demo? What's the close rate on the demo?

(00:35:00) Selling ShareFile to Citrix Solutions

(00:41:30) Several employees became millionaires because of options

(00:46:00) On selling ShareFile, "I can't decide whether I regret it or not."

(00:47:45) The origin of Raleigh Founded

(00:52:30) On starting Levitate - "I decided I was too young to retire."

Referenced:

• Startup Spotlight: Raleigh startup Levitate, led by Jesse Lipson, lands new partnership: https://wraltechwire.com/2022/03/08/raleigh-startup-levitate-led-by-jesse-lipson-lands-new-partnership/
• Citrix buys cloudy storage biz ShareFile: https://www.theregister.com/2011/10/13/citrix_buys_sharefile/
• Progress acquires file management platform ShareFile for $875M: https://techcrunch.com/2024/09/09/progress-acquires-file-management-platform-sharefile-for-875m/

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.