Triangle Tweener Talks

What drives someone to leave a cushy corporate role, start (and sometimes stumble at) multiple tech ventures, and finally build one of the Triangle’s most iconic unicorns?

On this episode of Triangle Tweener Talks, we sit down with Todd Olson, Founder and CEO of Pendo—a leading product analytics platform now powering hundreds of the world’s top software experiences.

Todd pulls back the curtain on his early days coding in a ...

How do you grow a 350-person, globally distributed tech company—without outside venture funding?

In this episode of Triangle Tweener Talks, we chat with Peter Zaitsev, Co-Founder of Percona, who bootstrapped his open-source database services and software company from a scrappy two-person startup in the U.K. to a $50M+ revenue business headquartered right here in the Triangle.

Peter’s story is anything but linear. He talks a...

How do you turn a simple “what if?” into a thriving venture—especially when you’re blending creativity, technology, and a dash of entrepreneurial courage?

In this episode of Triangle Tweener Talks, we sit down with Tina Tang, Co-Founder and CEO of Bristles, an AI-driven platform that helps furniture refinishers and DIYers reimagine their projects before picking up a single paintbrush.

Tina shares her journey from civil engin...

How do you transition from corporate life to building a successful startup? What does it take to create a company culture where people genuinely enjoy working while navigating the challenges of entrepreneurship?

In this episode of Triangle Tweener Talks, Scot Wingo sits down with Robbie Allen, a serial entrepreneur and founder of companies like StatSheet, Automated Insights, and Bionic Health. Robbie shares his jour...

How can technology close the healthcare gaps that leave so many underserved? What does it take to build a startup that challenges the status quo while navigating the ups and downs of entrepreneurship?

In this episode of Triangle Tweener Talks, we sit down with Dr. Joy Bhosai, founder and CEO of Pluto Health, to explore the inspiring journey that led her from global healthcare work to founding a tech startup aimed at improvi...

What does it take to embrace your unique strengths, navigate the dynamics of power and status, and achieve the success you deserve?

In this episode of Triangle Tweener Talks, we sit down with Dr. Alison Fragale, author of Likable Badass: How Women Get the Success They Deserve. Alison is a distinguished professor at UNC’s Kenan-Flagler Business School and a former McKinsey consultant with deep expertise in organizational psy...

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 approac...

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...

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...

According to her LinkedIn headline, Jan Davis has "doubled the size of three different businesses in different industries in three years or less as an operator."

Amazing, but what's even more impressive is that she started her entrepreneurial journey in the 1980's, when female founders were few and far between.

Today we hear her story of founding companies in the 80's and 90's, and what she's doing now as a Board member, ang...

As a Morehead Scholar UNC grad, and with a successful start to his career at Bain Capital, Alex Lassiter could have done anything next.

He chose entrepreneurship, which led to him living in Atlanta over a Chinese restaurant, so poor that he was calculating the cost of beans with his other cofounders and eating blue chicken.

He had dozens of ideas that failed.

And then one hit big.

Today, Alex shares his entrepreneurial journey...

Welcome to Triangle Tweener Talks, where we share stories from founders about how they got to where they are today.

The first founder we’re hearing from is the man who will be hosting this podcast - serial entrepreneur and general partner of the Triangle Tweener fund, Scot Wingo.

Where to Find Scot Wingo:

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