Triangle Tweener Talks

Four teenage friends decide to build the world’s first Windows-based email program—and then go on to launch a second venture that scores a legendary dot-com outcome. In this episode of Triangle Tweener Talks, host Scot Wingo sits down with Chris Evans, co-founder of DaVinci Systems (founded in 1985!) and Accipiter, to uncover the wild backstory behind pioneering email software, negotiating with Microsoft, and navigating the frenzied dot-com bubble.Chris shares personal lessons from youth, success, and heartbreak—including how he found his entrepreneurial tribe at Enloe High School, got “fired” by his best friend at age 27, and figured out that choosing the right market timing can change everything. Tune in to hear:Teenage Startup Roots. How meeting future co-founders on a school bus led to DaVinci Systems.DaVinci’s Email Revolution. Building the first GUI email for Windows—and why Microsoft featured them.Being Bought vs. Going Public. Lessons from turning down acquisition offers and facing Microsoft’s “friendly” competition.Personal Ups & Downs. Chris’s 1992 “firing” by best friend and CEO, and how it reshaped his outlook.Accipiter & the Dot-Com Boom. Shifting from publishing tech to ad-server SaaS and meeting the right investors.Epic CMGI Deal. The exit that turned a 25K check into 1 million and made everyone in the Triangle take notice.Where to Find Chris Evans:Linkedin: https://www.linkedin.com/in/chrisevans3/Where to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:[00:00:03] From High School to DaVinci[00:05:03] Building First Windows Mail[00:14:00] Turning Down Big Buyers[00:26:00] DaVinci’s Missed Exits[00:32:00] Fired by a Friend[00:42:22] Accipiter Launch[00:53:08] The CMGI Deal[01:02:00] Key Lessons LearnedIn the news:Interview with Chris Evans: the man who created email and online advertising: https://www.netimperative.com/2021/01/08/interview-with-chris-evans-the-man-who-created-email-and-online-advertising/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/

What happens when you grow up on a tobacco farm in rural North Carolina, turn down a million-dollar offer from Microsoft, and then build multiple groundbreaking software companies? In this episode of Triangle Tweener Talks, host Scot Wingo sits down with Richard Holcomb—serial founder, mentor, investor, and a driving force in the Triangle’s tech scene.Richard recounts his early days in Whiteville, NC, shares the backstory of his game-changing Microsoft Excel royalty deal (yes, it’s taught at Microsoft as a cautionary tale!), and reveals how he built and exited startups like DataDirect, HAHT Software, and StrikeIron—right through the dot-com booms and busts. From organic farming to “hillbilly negotiation,” Richard’s story is a fascinating blend of life lessons, tactical advice, and big-picture trends shaping the future of tech M&A.Tune in to hear:Why Richard turned down a lump-sum Microsoft buyout and got monthly royalties instead.The rise and fall of early Triangle startups—from mainframe code to dot-com mania.How he used “hillbilly negotiation” to outmaneuver corporate giants in high-stakes deals.Why paying it forward is so important and how Richard became a mentor and angel investor for dozens of Triangle founders.The secrets of M&A success in today’s market and why “Rule of 40” matters more than ever.Life after software—including Richard’s two-decade stint as an organic farmer and restaurateur.Where to Find Richard Holcomb:Linkedin: https://www.linkedin.com/in/richard-holcomb-b427a/North Carolina Venture Capital Fund: https://www.ncvcf.com/Corum Mergers and Acquisitions: https://www.corumgroup.com/Where to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:[00:00:03] Farm to Tech[00:05:03] Early Developer Tools[00:14:00] Hillbilly Negotiation[00:18:06] Turning Down Microsoft[00:26:00] Excel Royalty Windfall[00:31:20] HAHT, Dot-Com Crash[00:42:00] StrikeIron and Web Services[00:47:00] Farm Life Experiment[00:54:00] M&A, Consolidation WaveIn the news:Confessions of a serial entrepreneur: https://www.bizjournals.com/triangle/inno/stories/inno-insights/2021/09/14/confessions-of-a-serial-entrepreneur.htmlFarmer to table: Tales and recipes from a fiercely local kitchen: https://www.newsobserver.com/living/food-drink/article172064357.htmlFresh Direction: A Farm-to-Table Restaurant (Published 2010): https://www.nytimes.com/2010/04/25/magazine/25food-t.html---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/

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 bank at age 14, his near-miss exits that fueled an enduring chip on his shoulder, and how he and his co-founders built Pendo into a 900-person juggernaut. Along the way, Todd dives into the heart of “Founder Mode,” evolving your culture (when everyone’s giving you a million reasons not to), and why relentless customer focus might just be the ultimate growth hack.Tune in to hear:Todd’s Unlikely Start in Tech: How a 14-year-old data-entry temp turned into a Unix-wielding problem solver at a major bank.Roller-Coaster Beginnings: The heartbreak of Todd’s first ventures, what went wrong—and why he kept going.Building Pendo from Scratch: The aha moment that sparked a mission to help software companies measure adoption and drive true customer value.Scaling to 900+ People: How Todd keeps the magic of a small startup culture alive while serving a global enterprise customer base.Customer-Obsessed Leadership: Why Todd personally calls customers with less-than-stellar feedback and how it’s created a near-cult following among Pendo users.Founder Mode & Culture Shifts: Hear Todd’s take on revamping core values mid-flight, returning to in-person collaboration, and leaning in on product.Raising Capital vs. Growing the Pie: Practical wisdom on why picking the right investors (and not sweating ownership percentages) is a path to real success.Where to Find Todd Olson:Linkedin: https://www.linkedin.com/in/toddaolson/Pendo: https://www.pendo.io/X: https://x.com/tolsonWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:[00:05:03] Ringing the Gong & Celebrating DealsTodd shares a big customer win, the excitement around “gong moments,” and why team collaboration fuels success.[00:07:48] Bank Life at 14: Todd’s Early Tech OriginsHear how Todd’s mom bragged to the right person at the right time, launching him into a data-entry job turned accidental programming career.[00:12:55] First Startup Heartbreak: CerebellumTodd recounts his early venture, the near-miss acquisition, and the board drama that ultimately shaped his “chip on the shoulder.”[00:18:06] TogetherSoft & 250 Engineers in RussiaManaging a global dev team while hopping planes monthly—Todd explains the pressure cooker that taught him real product management.[00:25:45] M&A Lessons at Borland & Working with Frank SlootmanTodd gets a front-row seat to high-powered leadership under a now-legendary CEO and learns what high growth really looks like.[00:31:20] Sixth Sense & the 2008 CrunchDiving into Todd’s second startup, nearly running out of money, and how radical transparency pulled the team together at the eleventh hour.[00:39:10] Rally Software’s IPO & the Enduring ChipWriting parts of the S-1, standing on the NYSE balcony—yet realizing it wasn’t truly his company, pushing Todd to keep going.[00:44:45] Founding Pendo & Picking Co-FoundersWhy Todd returned to Raleigh for his next venture, how the early Pendo crew came together, and the story behind the name.[00:52:15] Choosing the Right InvestorsTodd recalls how a single “yes” check started the seed round—but why aligning with good humans is even more critical than a big valuation.[01:05:05] The Power of Customer ObsessionFrom personal phone calls to instant problem solving, Todd reveals why old-school “MBNA-style” service still wins hearts in SaaS.[01:08:10] Entering ‘Founder Mode’ & Betting on AITodd opens up about reinvigorating Pendo’s culture post-COVID, re-committing to product, and the looming wave of AI-driven software.In the news:Pendo CEO talks ‘founder mode,’ going public and his Raleigh software firm’s first profit: https://www.newsobserver.com/news/business/article293725529.htmlHow Todd Olson of Pendo Got His First Customers: https://www.inc.com/alexa-von-tobel/todd-olson-pendo-customer-journey.htmlOlson’s ambitious journey: https://www.bizjournals.com/triangle/news/2022/04/08/todd-olson-leads-pendo-ambitious-journey.html---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/

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 about growing up in the Soviet Union, teaching himself assembly code on paper before he even touched a real computer, and starting his first company at age 19—where he quickly realized that “business risk is one thing, but risking a kidney is something else!” After stints with MySQL and a move to Seattle, he eventually settled down in Durham, North Carolina, growing Percona into an open-source industry leader that competes on pure value and top-tier support.Whether you’re an early-stage founder, a bootstrapper at heart, or just love the behind-the-scenes tales of pioneering in open source, this episode is packed with candid lessons on innovation, risk tolerance, and how to “grow or go” without losing sight of what matters to you and your customers.Tune in to hear:Peter’s early days in Russia, learning to code by writing programs on paper.The rise of open-source databases—and how Percona survived and thrived in the wave of cloud, AWS, and managed solutions.Peter’s take on bootstrapping vs. taking venture capital, plus how he steered Percona to $50M+ in revenue with zero outside funding.How his zero-to-one mindset paved the way for other ventures like Altinity, FerretDB, and Coroot.Why he chose to relocate Percona (and his family) to the Triangle—and how he learned he’s more of a “small team, big ideas” guy than a 350-person operator.Where to Find Peter Zaitsev:Linkedin: https://www.linkedin.com/in/peterzaitsev/PeterZaitsev.com: https://peterzaitsev.com/Percona: https://www.percona.com/Instagram: https://www.instagram.com/peterzaitsev/Where to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:(00:03:44) Growing Up in the Soviet Union: Peter describes learning code by writing assembly on paper and dreaming of real computers.(00:08:09) Founding Spylog at 19: The excitement (and danger) of launching a web analytics startup in late ’90s Russia—“equity or a kidney” decisions included.(00:13:15) MySQL & the Open-Source Spark: How Peter’s early clashes (and collaborations) with MySQL’s founders shaped his approach to open-source performance.(00:26:30) Leaving MySQL & Moving to the UK: Peter’s leap from a corporate gig to founding Percona in London—and how consulting work morphed into something bigger.(00:30:33) Percona Lands in California: Navigating the 2008 financial crisis, Sun’s acquisition of MySQL, and the unexpected tailwinds for open-source databases.(00:40:01) Why the Triangle? Peter shares what drew him (and eventually Percona) to Durham, NC—seasons, startup culture, and less traffic than Silicon Valley!(00:45:45) MySQL vs. PostgreSQL in the Cloud Era: The shifting momentum in open-source databases and why “tuning by credit card” happens on AWS and beyond.(00:52:10) Building an Open-Source Ecosystem: From support subscriptions to new ventures like Altinity and Coroot—Peter explains his passion for transparent software.(00:59:10) The Zero-to-One Founder Mentality: Why Peter thrives on the excitement of small, agile teams—and how he handles “too many good ideas” before breakfast.(01:03:05) CEO Lessons: Knowing when to hire a CEO, evolving as a founder, and final thoughts on putting customers (not licenses) first.In the news:Percona Redefines Cloud-Native Database Management with Percona Everest: the World's First Open Source Public DBaaS Alternative: https://www.businesswire.com/news/home/20240917948450/en/Percona-Redefines-Cloud-Native-Database-Management-with-Percona-Everest-the-Worlds-First-Open-Source-Public-DBaaS-AlternativePercona Percolates, Permeates & Penetrates To Platform Position: https://www.forbes.com/sites/adrianbridgwater/2022/05/17/percona-percolates-permeates--penetrates-to-platform-position/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/

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 engineering and data analytics into the world of startups, navigating the messy middle of product-market fit, and iterating her way from a broad concept to a laser-focused solution for a passionate niche audience. She talks candidly about how she used customer interviews, no-nonsense feedback, and evolving AI tools to refine Bristles into a tool that’s now cutting DIY project mock-up time from hours to minutes.Tune in to hear:How Tina discovered her target market by starting broad and then homing in on furniture refinishers.The gritty reality of early product-market fit—what it looks like, why it’s so hard, and how to push through.Lessons learned from 200+ customer discovery calls: turning “cool tech” into a practical, must-have tool.How evolving AI capabilities, from generative models to segmentation tools, gave Bristles the edge it needed.The value of starting small, embracing “good enough for now,” and letting customer feedback guide your next big move.Where to Find Tina Tang:Linkedin: https://www.linkedin.com/in/tina-tang-uva/Website: https://bristles.ai/X: https://x.com/stocasiaaiWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn this episode:(00:06:23) Immigrant Sacrifices and the American Dream(00:13:27) Modeling Brain Functions Through Code Replication(00:16:34) Legacy System Analysis for Modernization Success(00:21:50) Advancements in Neural Networks and AI Technology(00:27:47) Revolutionizing Photo Editing with Generative Models(00:30:31) Geographical Constraints in Adobe's AI Product Management(00:38:06) Interactive AI Photo Painting Tool Development(00:46:26) Precision Photo Editing Tool for Home Improvement(00:55:58) Enhancing User Experience Through Feedback Insights(01:02:30) Bristles and Simplifying Furniture Design Tools(01:15:52) Demand-Driven Strategy for Business Success(01:18:15) Zero Friction Addiction: Customer Engagement StrategiesIn the news:Hidden Gems: Meet Tina Tang: https://voyageraleigh.com/interview/hidden-gems-meet-tina-tang-of-bristles/Meet Our Founders: Tina Tang & Anthony Alers: https://ncidea.org/meet-our-founders-tina-and-anthony/Startup Spotlight: Bristles.ai uses AI to help folks DIY home design: https://wraltechwire.com/2022/02/08/startup-spotlight-bristles-ai-uses-ai-to-help-folks-diy-home-design/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/

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 entrepreneurshipWhy creating a positive work environment leads to better outcomesHow adaptability and pivoting can make or break a startupThe role of Product-Led Growth strategies in scaling businessesRobbie’s thoughts on blending passion with expertise to build something impactfulWhere to Find Robbie Allen:Linkedin: https://www.linkedin.com/in/robbieallen/Website: https://www.bionichealth.com/X: https://x.com/robbieallenWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn 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-beingIn 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/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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 HealthThe importance of resilience in navigating the highs and lows of startup lifeJoy’s approach to leveraging tech to solve healthcare disparitiesStrategies for securing funding and building partnerships in the health tech spaceWhy focusing on patient experiences is key to driving innovationWhere 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/joybhosaimdWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn 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 networkIn 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.html2024 Women in Business Awards Winners: https://www.bizjournals.com/triangle/c/2024-women-in-business-awards-raleigh-durham/22541/joy-bhosai-pluto-health.htmlMedable 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---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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 advantageWhy setting boundaries in negotiations is a critical (and likable) power moveThe importance of building relationships early for entrepreneurial successPractical tips for navigating the unique challenges female founders faceHow Alison’s own journey has shaped her perspective on leadership and influenceAlison’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/0385549148Where to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn 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---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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 successHis decision-making process behind skipping VC fundingThe inside scoop on selling to private equity and the power of the double exitFounder tips on distribution and go-to-market strategyA preview of what’s next for Dusan BabichWhere to Find Dusan Babich:Linkedin: https://www.linkedin.com/in/dusanbabich/X: https://x.com/dusanbabichInstagram: https://www.instagram.com/dusanbabichWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn 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 SelfReferenced: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/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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/robbiehardydotcomRobbieHardy.comWhere to Find Scot Wingo:Linkedin: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingoIn 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---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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-625195X: https://x.com/jesselipsonLevitate: 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/scotwingoIn 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/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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/scotwingoIn 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 FundReferenced: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/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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/scotwingoIn 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 GreenPlacesReferenced: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.htmlGreenPlaces 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---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------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/scotwingoIn 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 FundReferenced: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_ilacBdzv4Wingo steps down as Spiffy CEO: https://businessnc.com/wingo-steps-down-as-spiffy-ceo/---Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence. ------Triangle Tweener Talks is sponsored by:Atomic Object: https://atomicobject.com/