NC Tweener Talks

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 journey from working at tech giants like IBM and Cisco to launching startups that merge technology with meaningful impact.

Robbie discusses how he fosters positive workplace environments, prioritizes growth over immediate revenue, and adapts to challenges like shifting business models. His unique approach to entrepreneurship—rooted in transparency, adaptability, and a long-term vision—offers practical insights for anyone considering their own startup journey.

Tune in to hear:

• Robbie’s transition from corporate roles to entrepreneurship
• Why creating a positive work environment leads to better outcomes
• How adaptability and pivoting can make or break a startup
• The role of Product-Led Growth strategies in scaling businesses
• Robbie’s thoughts on blending passion with expertise to build something impactful

Where to Find Robbie Allen:

• Linkedin: https://www.linkedin.com/in/robbieallen/
• Website: https://www.bionichealth.com/
• X: https://x.com/robbieallen

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:

(00:02:11) 10th-Grade Business Machines Class - "I want to do this rest of my life."

(00:08:13) IBM, Cisco, and the Vision of Staying at a Company for 30 Years

(00:14:07) Discovering the Warts of Being at a Huge Company

(00:29:02) Winning a $50K NC IDEA Grant
(00:32:06) Acquisition Offers and a Trip to ESPN

(00:38:14) Crazy Monetization Strategy

(00:47:00) Changing Perceptions in Securing Startup Funding

(00:50:49) Yahoo and 10M Fantasy Football Recaps

(00:54:07) Vista's Aggressive Acquisition of Automated Insights

(00:57:03) Tech Industry Success through Strategic Collaborations

(01:04:20) Automated Insights' Ripple Effect on Entrepreneurship

(01:09:43) Challenges Faced in Infinea ML's Journey

(01:13:17) Strategic Shift: Consulting to Product Development Success

(01:19:18) Bionic Health: Transforming Preventative Healthcare with Data

(01:23:47) Optimizing Health for Extended Well-being

In this news:

• Serial entrepreneur Robbie Allen launches new AI health venture, raises $3M: https://wraltechwire.com/2023/03/21/serial-entrepreneur-robbie-allen-launches-new-ai-health-venture-raises-3m/
• Duke-inspired, Robbie Allen-led Infinia taps machine learning trend: https://businessnc.com/duke-inspired-robbie-allen-led-infinia-taps-machine-learning-trend/
• Vista Acquires Automated Insights, The Startup Behind The AP’s “Robot” News Writing: https://techcrunch.com/2015/02/12/automated-insights-the-startup-behind-the-aps-robot-news-writing-gets-acquired-by-vista/

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 improving patient outcomes. Joy’s background spans experiences at the Clinton Foundation’s Ethiopia Hospital program, a Fulbright scholarship in Thailand, and a Duke University residency that sparked her passion for health tech innovation.

Joy opens up about her challenges raising capital during the pandemic, the triumphs of building Pluto Health, and the unique insights she’s gained from her “Rocket Coaster” entrepreneurial ride. Along the way, she shares how her parents’ work with adults with intellectual disabilities influenced her mission to create solutions that are patient-centric, equitable, and impactful.

Tune in to hear:

• How Joy transitioned from clinical practice to founding Pluto Health
• The importance of resilience in navigating the highs and lows of startup life
• Joy’s approach to leveraging tech to solve healthcare disparities
• Strategies for securing funding and building partnerships in the health tech space
• Why focusing on patient experiences is key to driving innovation

Where to Find Dr. Joy Bhosai:

• Linkedin: https://www.linkedin.com/in/joy-bhosai-md-mph-0475317/
• Website: https://www.trypluto.com/
• X: https://x.com/joybhosaimd

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:

(00:03:06) Joy learned entrepreneurship from her parents

(00:07:29) Global Health Education at Yale

(00:11:23) "We just need better access to basic resources like medicine and water. Why are we making a smartphone app?"

(00:17:26) "I initially didn't think about starting Pluto as a startup at all."

(00:28:08) Starting to commercialize Pluto in mid-2022

(00:32:30) Raising $2.5M Pre-seed

(00:34:51) Leveraging strategic Healthcare Funding Partnerships

(00:45:38) "Imagine being able to with a click of a button, have someone show up to your house the next day, draw blood while you're drinking coffee and have it be done with."

(00:55:58) Leaning on friends and finding a founder network

In this news:

• Pluto Health Extends Support for Those Impacted by Hurricane Helene in Western NC and Eastern TN: https://www.prnewswire.com/news-releases/pluto-health-extends-support-for-those-impacted-by-hurricane-helene-in-western-nc-and-eastern-tn-302280487.html
• 2024 Women in Business Awards Winners: https://www.bizjournals.com/triangle/c/2024-women-in-business-awards-raleigh-durham/22541/joy-bhosai-pluto-health.html
• Medable Partners with Pluto Health to Optimize Patient Experience and Improve Access to Clinical Trials: https://www.businesswire.com/news/home/20231003413736/en/Medable-Partners-with-Pluto-Health-to-Optimize-Patient-Experience-and-Improve-Access-to-Clinical-Trials

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 psychology. Her mission? To empower female founders—and leaders of all genders—to build influence, negotiate effectively, and claim their rightful place at the table.

We discuss the core principles of Alison’s book, exploring the fascinating interplay between power and status and how women can use these insights to overcome workplace challenges. Later, we shift gears to discuss how female founders can apply psychological frameworks to secure capital, forge critical relationships, and thrive in the startup ecosystem.

But Alison’s message isn’t just for women. The frameworks, strategies, and real-world examples shared in this episode offer universal lessons for any founder or leader looking to level up their negotiation skills, leadership approach, or influence.

Tune in to hear:

• The surprising relationship between power, status, and likability—and how to use it to your advantage
• Why setting boundaries in negotiations is a critical (and likable) power move
• The importance of building relationships early for entrepreneurial success
• Practical tips for navigating the unique challenges female founders face
• How Alison’s own journey has shaped her perspective on leadership and influence
• Alison’s actionable advice for leveraging your LinkedIn presence, building your network, and positioning yourself as a leader in your industry.

Where to Find Dr. Alison Fragale:

• Linkedin: https://www.linkedin.com/in/alisonfragale/
• Website: https://alisonfragale.com/
• Instagram: https://www.instagram.com/alisonfragale/
• Substack: https://alisonfragale.substack.com/
• Likeable Badass: How Women Get the Success They Deserve: https://www.amazon.com/Likeable-Badass-Women-Success-Deserve/dp/0385549148

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:

(00:02:37) McKinsey to UNC to Likeable Badass

(00:09:47) Should UNC Have a Likeable Badass Academy?

(00:14:30) How the Book Came to Be

(00:19:59) Most Books are "Power Leads and Status Follows". Not This One

(00:25:19) What It Does and Doesn't Mean to be a Servant Leader

(00:35:45) "You can't build anything if you can't work with people and you can't influence people."

(00:39:41) Proactive Relationship Building for Female Founders

(00:44:03) When the First Idea Doesn't Work...

(00:55:10) The Interpersonal Circumplex and What That Means for Leaders

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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, angel investor, and recent co-founder of the RTP Angel Fund.

Where to Find Jan Davis:

• Linkedin: https://www.linkedin.com/in/janldavis/
• RTP Angel Fund: https://www.rtpangelfund.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:

(00:02:07) They told me I was a risky hire because I was a woman.

(00:05:53) What Jan learned by pitching to Chevrolet.

(00:10:06) Jan's first exit, selling to AT&T.
(00:11:30) Jan's first company death.
(00:13:00) My son had his first bottle in a Board meeting.
(00:15:00) The next business, raising capital, getting to $20M, and then...

(00:18:52) Transition to Warsaw, Poland

(00:26:59) Legacy Systems Technical Debt in Direct Marketing

(00:30:25) Digital Marketing Transformation

(00:36:11) Real-time Testing Revolutionizes Marketing Strategies

(00:44:01) Binocular Technology for Retail Analysis

(00:49:01) Optimizing Retail Operations through Data Analysis

(01:02:45) Technology-Driven Angel Investing with Triangle Angel Partners

(01:15:33) Starting the RTP Angel Fund

Referenced:

• New angel investor fund launches in Triangle with high-profile backers: https://wraltechwire.com/2023/08/10/new-angel-investor-fund-launches-in-triangle-with-high-profile-backers/

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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 with host Scot Wingo.

Where to Find Alex Lassiter:

• Linkedin: https://www.linkedin.com/in/%F0%9F%8C%8F-alex-lassiter-b6673b8/
• Website: https://greenplaces.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:

(00:01:59) "I was always an idea a minute person..."

(00:03:42) Alex's first giant check

(00:07:24) He could have been gorged by a bull or met the love of his life

(00:09:27) Alex the Bain intern wins a pitch competition

(00:13:30) Hitting up all the Bojangle's on the East Coast

(00:19:30) The first startup was called Frequenter, which was supposed to be a better Yelp. Then 3 more companies...

(00:20:10) Table, a new app for last minute reservations

(00:25:50) Living above a Chinese restaurant in Atlanta, trash blowing in every day, and eating blue chicken
(00:28:30) You know you're poor when you're calculating cost per bean

(00:29:30) Starting Gather and the first $45K investment

(00:39:30) Learning the SDR model for growth

(00:40:30) Another raise for Gather - this time 7 figures

(00:44:00) Acquiring a competitor
(00:46:30) Vista Equity comes calling -> Gather Exit

(00:53:00) Drake, Ferraris, and Neil Degrasse Tyson
(01:30:00) Starting again with GreenPlaces

Referenced:

• Raleigh sustainability software startup GreenPlaces looks to grow with $13M in funding: https://wraltechwire.com/2023/06/21/raleigh-sustainability-software-startup-greenplaces-looks-to-grow-with-13m-in-funding/
• Triangle entrepreneurs pour $3M into Raleigh ESG startup: https://www.bizjournals.com/triangle/inno/stories/fundings/2022/08/26/raleigh-esg-startup-green-places-new-funding.html
• GreenPlaces Secures $4M in Seed Funding led by Felicis: https://www.prnewswire.com/news-releases/greenplaces-secures-4m-in-seed-funding-led-by-felicis-301648505.html

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

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/scotwingo

In this episode:

(00:01:30) Bill Gates and Mark Zuckerberg? That's not my story.
(00:05:30) Here's how to get a lamborghini.
(00:08:00) USC, first job, meeting Dr Miller at NC State, and being infamous in a bad way.
(00:14:00) We started Stingray Software
(00:16:30) Exit, how Star Wars inspired AuctionRover.com, and the first multi-million $ check
(00:22:00) ChannelAdvisor -> 800 employees
(00:28:00) Ringing the NYSE bell
(00:32:50) What if I reimagined car care?
(00:34:30) Starting the Tweener List -> Triangle Tweener Fund

Referenced:
The FORTUNE Magazine Cover with Bill Gates that Changed it All: https://pbs.twimg.com/media/FgLns-9WQAAjxsF?format=jpg&name=large
"Scot Wingo, a serial entrepreneur ‘paying it forward’": https://wraltechwire.com/2019/12/31/tech-legends-scot-wingo-a-serial-entrepreneur-paying-it-forward/
Scot on Mad Money: https://www.youtube.com/watch?v=7_ilacBdzv4
Wingo steps down as Spiffy CEO: https://businessnc.com/wingo-steps-down-as-spiffy-ceo/

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

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/