Triangle Tweener Talks

By: Triangle Tweener Fund
Listen for free

  • Summary

  • A podcast for builders by builders in the Triangle. We explore the startup journey and stories with local Triangle founders, from the idea to the exit and everything in between. Hosted by serial entrepreneur and founder of the Triangle Tweener Fund Scot Wingo, and produced by Earfluence.
    2024 Triangle Tweener Fund
    Show More Show Less
Show More Show Less
activate_Holiday_promo_in_buybox_DT_T2
Episodes
  • Todd Olsen, CEO of Pendo: Pendo Founding story and What Makes Him Tick?

    Todd Olsen, CEO of Pendo: Pendo Founding story and What Makes Him Tick?
    Jan 9 2025
    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/
    Show More Show Less
    1 hr and 30 mins
  • Peter Zaitsev: Open-Source Entrepreneurship and the Percona Story

    Peter Zaitsev: Open-Source Entrepreneurship and the Percona Story
    Jan 2 2025
    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/
    Show More Show Less
    1 hr and 32 mins
  • Tina Tang: Finding Product-Market Fit, Raising Pre-Seed, and the Bristles.AI Story

    Tina Tang: Finding Product-Market Fit, Raising Pre-Seed, and the Bristles.AI Story
    Dec 19 2024

    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/stocasiaai

    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:

    (00:06:23) 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 Strategies


    In 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/
    Show More Show Less
    1 hr and 27 mins

What listeners say about Triangle Tweener Talks

Average customer ratings

Reviews - Please select the tabs below to change the source of reviews.

Audible.co.uk reviews

Amazon reviews
No Reviews are Available