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Host Ian Hathaway interviews Tony Summerville, founder and executive chairman of Fleetio, about building a $1.5 billion fleet optimization platform from Birmingham, Alabama. Summerville traces his Huntsville upbringing, summers spent working in his father's electrical supply business, competitive swimming background, early career at Regions, and time at Daxko, where he saw the shift toward web-based software and learned how SaaS businesses are built. After leaving a stable job with a one-year agreement with his wife Brittany, he spent months interviewing customers before writing a single line of code, using those conversations to validate fleet management as a painful, underserved problem. He describes Fleetio's early product discovery, the whiteboard moment that shaped its direction, capital-efficient growth, content-driven marketing, the discipline of building before chasing investor validation, and the difficult decision to kill a product that was pulling focus from the core business. They cover the transition from founder-CEO to executive chairman, scaling Fleetio while preserving culture, building from Birmingham, hybrid team design, supporting the next generation of local entrepreneurs, and the personal framework that helped him decide to start in the first place.
Show Notes:
(02:33) Huntsville Roots And Early Work Ethic
(08:43) Leaving Daxko And Taking The Leap
(11:53) Customer Interviews Before Code
(15:22) The Whiteboard That Became Fleetio
(20:19) Bootstrapping And Capital Efficiency
(22:52) The Wrong Kind Of Validation
(24:05) Killing A Product That Half Worked
(29:15) Knowing When To Step Aside
(35:34) Building From Birmingham
(39:44) Investing Back Into The Ecosystem
(43:56) Beyond The Bio with Tony Summerville
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guests: Tony Summerville - Founder & Executive Chairman, Fleetio
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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Host Ian Hathaway interviews Mitchell Green, founder and managing partner of Lead Edge Capital, about building one of growth equity's most unconventional firms by looking where others do not. Green traces his Grand Rapids upbringing, early paper routes, factory floor experience, ski racing path to Williams, failed college startup, and the lessons in persistence and networking that shaped his career. After starting at Bessemer as one of the firm's first cold callers, he learned outbound sourcing, pattern recognition, and the value of connecting people by speaking with thousands of companies. He describes buying investments out of a struggling hedge fund after the financial crisis, raising Lead Edge's first $52 million fund, the Alibaba investment that helped put the firm on the map, and the operator LP network that became one of Lead Edge's defining advantages. They cover the firm's eight investment criteria, its focus on profitable and capital-efficient companies, creative deal structures, investing outside Silicon Valley, the founder traits Green looks for, the AI productivity boom, mentorship, legacy, and the personal intensity behind his work.
Show Notes:
(04:40) Grand Rapids Roots And Factory Floor Lessons
(06:49) Failed Startup And The Power Of Networking
(09:33) Bessemer And The Cold Calling Apprenticeship
(11:45) Learning The Strike Zone
(15:22) Turning LPs Into An Operator Network
(18:24) Persistence As The Founder Edge
(20:48) Finding Builders Outside Silicon Valley
(21:46) The Lead Edge Eight
(23:26) Outbound Sourcing At Scale
(24:19) Creative Deal Structures And Risk Discipline
(29:32) AI, Productivity, And The Long Term
(32:57) Legacy, Mentorship, And Follow-Through
(35:15) Beyond The Bio with Mitchell Green
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guests: Mitchell Green - Co-Founder & Managing Partner, Lead Edge Capital
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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Fehlende Folgen?
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Host Ian Hathaway interviews Garrett Langley, founder and CEO of Flock Safety, about building public safety technology with a mission to eliminate crime. Langley traces his Atlanta upbringing, his early computer repair business, lessons from his father's relationship-driven sales approach, and his early career successes, including the acquisitions of Firethorn and Experience. After a post-exit identity crisis, he prioritized building with the right team and launched Flock after neighborhood break-ins revealed law enforcement needed actionable license plate data. He describes early traction, Y Combinator struggles, near-pivot moments, media-driven go-to-market, and a difficult fundraise amid skepticism about Atlanta, hardware, and law enforcement. They cover rapid scaling, new products, privacy and regulation debates, immigration-enforcement concerns, Atlanta ecosystem advantages, the Thriving Cities Fund, explicit culture-building, and the personal support system sustaining his leadership.
Show Notes:
(02:28) Burden of Responsibility
(06:47) Atlanta Roots and Early Hustle
(12:19) Two Big Exits and Crisis
(15:35) Flock Origin Story
(20:59) YC Breakthrough and Media
(23:19) Series B Near Miss
(26:23) Scaling Innovation and Vision
(29:45) Fatherhood and What Matters
(30:36) Safety As A Right
(31:31) Scrutiny And Tradeoffs
(38:13 Building In Atlanta
(40:18) Diamonds In The Rough
(42:13) Thriving Cities Fund
(44:50) Writing Culture Down
(51:12) Legacy And Safe Cities
(53:22) Beyond The Bio with Garrett Langley
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guests: Garrett Langley - Founder & CEO, Flock
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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Host Ian Hathaway continues The Outsider Playbook by pulling the next set of patterns that show up after outsiders have already proven they can build. Part 2 is about what lasts: culture that can operate without the founder in every room, the rituals that turn values into behavior, and the hard identity work that hits when the company changes shape or you step away. Along the way, Ian connects lessons from Kyle Porter, David Cohen, Dug Song, Scott Dorsey, Shegun Otulana, Gail Goodman, Jewel Burks Solomon, Jimena Pardo, Melodie van der Baan, Brad Feld, Linda Rottenberg, and others on hiring and standards, "better not bigger" discipline, post-exit emotional reality, separating the role from the person, and how success compounds when founders pay it forward and invest energy into their communities.
Show Notes:
(03:05) Culture as the operating system, not a "nice to have"
(06:00) Why culture must be reinforced through rituals as you scale
(07:00) "Appreciations" and making excellence visible and repeatable
(09:00) Orange culture: turning values into a shared identity that survives scale
(12:00) "Better not bigger" and resisting growth that erodes standards
(18:00) The emotional reality after a win: rumination, grief, and getting it on the page
(24:00) Founder identity fusion: when the role becomes the person
(26:00) You are not a hat: separating who you are from what you do
(30:00) The post-exit gap between the headline and how it actually feels
(33:00) Give First flywheels and putting energy in without a defined return
(36:00) Generating belief: building gravity when the world is not watching
(41:00) Startup communities as the durable force, more powerful than any one company
(45:00) The ecosystem multiplier: turning one win into infrastructure for the next wave
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guests: Kyle Porter, Salesloft; Wade Foster, Zapier; Shegun Otulana, TheraNest, Harmony Venture Labs; Dug Song, Duo Security; Scott Dorsey, ExactTarget, High Alpha; David Cohen, Techstars; Gail Goodman, Constant Contact; Jewel Burks Solomon, PartPic, Collab Capital; Sean O'Sullivan, MapInfo, SOSV; Melodie van der Baan, Max Retail; Jimena Pardo, Carrot, Hi Ventures; Jason Seats, Slicehost, Techstars; Brad Feld, Foundry, Techstars; Linda Rottenberg, Endeavor; Jon Lensing, OpenLoop; Hernan Kazah, Mercado Libre, Kaszek
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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Host Ian Hathaway marks 25 episodes of Outsider Inc. by stepping back to synthesize an emerging "outsider playbook" from founders, investors, and ecosystem builders succeeding outside traditional venture hubs. The episode focuses on underestimation and constraint as structural advantages: being dismissed builds hunger and calluses; small markets force repeatable systems and early scaling; capital scarcity creates discipline and focus; missing infrastructure pushes founders to build more comprehensive, defensible solutions; and lived customer pain produces deeper insight. Stories include Mercado Libre's rise from Argentina amid skepticism, Zapier's Central Missouri origins, SendGrid's work-ethic forged by hardship, investors doubting Partpic even amid an Amazon offer, and lessons from ExactTarget, EquipmentShare, OpenLoop, Duo Security, DoubleClick, and others on bootstrapping, resilience, learning from being wrong, and "failure is not an option."
Show Notes:
(02:14) Being Underestimated
(05:29) Proving Yourself Twice
(11:34) Constraint as Advantage
(12:11) Small Markets Scale Faster
(15:11) Capital Scarcity Discipline
(17:10) Missing Infrastructure Moats
(20:42) Outsider Toolkit Basics
(21:08) Bootstrapping and Optionality
(24:19) Focus and Early Revenue
(26:21) Hustle and Customer Grind
(28:04) Resilience Through Failure
(30:34) Gatekeepers and Being Early
(32:15) Learning From Being Wrong
(33:59) Irrational Commitment
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guests: Hernan Kazah, Mercado Libre, Kaszek; Wade Foster, Zapier; Isaac Saldana, SendGrid; Jewel Burks Solomon, PartPic, Collab Capital; Shegun Otulana, TheraNest, Harmony Venture Labs; Linda Rottenberg, Endeavor; Gail Goodman, Constant Contact; Willy Schlacks, EquipmentShare; Scott Dorsey, ExactTarget, High Alpha; Jon Lensing, OpenLoop; Dug Song, Duo Security; Jason Seats, Slicehost, Techstars; Sean O'Sullivan, MapInfo, SOSV; Guillaume de Zwirek, Artera; Michael Praeger, AvidXchange; Melodie van der Baan, Max Retail; Brad Feld, Foundry, Techstars; Kevin O'Connor, DoubleClick, Graphiq, ScOp; Chris Schroeder, Startup Rising, HealthCentral, Next Billion Capital Partners; Jared Polis, Governor of Colorado; AIS; Blue Mountain; Proflowers; Techstars
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway sits down with Colorado Governor Jared Polis, a serial entrepreneur and Techstars co-founder who has spent his career blending founder instincts with public service. Jared shares how he built and exited multiple tech companies early, including BlueMountain and ProFlowers, and what those years taught him about capital, timing, and learning by doing. They also unpack how a founder mindset translates inside government, why Congress felt more like entrepreneurship than executive leadership, and how Jared approached policy like a builder. Along the way, Jared discusses accredited investor reform, why wealth is a poor proxy for competence, and the practical systems thinking behind Colorado's biggest moves, from universal preschool and insulin price caps to Bitcoin tax payments and criminal justice reform. The conversation is a rare look at what happens when a repeat founder brings startup operating principles into politics, and what outsiders can learn from it.
Show Notes:
(03:00) Early work ethic, risk tolerance, and learning in the deep end
(07:00) Three exits before 30 and the pattern behind them
(10:00) Co-founding Techstars and the early days of backing founders
(14:00) Building and scaling ProFlowers and disintermediating the supply chain
(16:00) Running for Congress and stepping into public service
(20:00) Why Congress felt like entrepreneurship, not CEO leadership
(22:00) Founder mindset in policy and the push to rethink "qualified investors"
(23:00) Outcomes as governor, universal preschool, insulin caps, pardons, and more
(19:00) Bitcoin for taxes and treating government like a system you can improve
(32:00) Advice for first-time founders and why every new founder is an outsider
(34:00) Beyond the Bio: Jared Polis
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Jared Polis, Governor of Colorado; AIS; Blue Mountain; Proflowers; Techstars
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway sits down with Chris Schroeder, entrepreneur, investor, Co-Founder of Next Billion Ventures, and author of Startup Rising, to explore what American entrepreneurs and investors miss when they overlook the rest of the world. Chris reflects on a career spanning politics, media, venture-backed startups, and global investing, and shares how a 2010 trip to Dubai reshaped his thinking about entrepreneurship, emerging markets, and the future of innovation. They discuss the power of asking better questions, why humility matters more than certainty, what Silicon Valley often gets wrong about founders in other regions, and how time spent on the ground in places like the Middle East, Southeast Asia, Latin America, and China reveals patterns most people never see. Chris also shares lessons from building and selling HealthCentral, writing Startup Rising, investing through Next Billion Ventures, and why the best founders stay focused on real problems, not prestige.
Show Notes:
(03:00) Why asking better questions matters more than having all the answers
(05:00) The wonder of being wrong and learning through humility
(09:00) Family history, immigration, and the entrepreneurial mindset
(14:20) Politics, transactional relationships, and the long game of trust
(20:10) Building inside the Washington Post during digital disruption
(27:45) The HealthCentral thesis and why community can save lives
(33:10) The Dubai trip that changed Chris Schroeder's life
(38:00) Writing Startup Rising and seeing what others missed in the Middle East
(41:30) Why global founders need to be understood on their own terms
(50:45) What Chris learns by getting on the ground in China
(55:20) The questions American entrepreneurs and investors should be asking now
(58:45) The danger of "third cappuccino syndrome" and losing focus on what matters
(1:00:00) Beyond the Bio: Chris Schroeder
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Chris Schroeder, Next Billion Ventures; Author of Startup Rising; former CEO, HealthCentral
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway sits down with Willy Schlacks, Co-Founder and President of EquipmentShare, to explore what it really looks like to build a category-defining company outside Silicon Valley. Willy shares how EquipmentShare grew from operator pain in the field into a vertically integrated construction tech platform spanning technology, equipment, and services, and why embracing constraint can be a strategic advantage, not a limitation. They dig into the chaos of jobsite operations, the early decision to take a platform approach, what Willy learned from time inside Y Combinator, and how building from Missouri forced the company to master scale early. Willy also reflects on taking EquipmentShare public at a $7B valuation, building the startup ecosystem through Redbud VC, and what he looks for in founders when the hard part is still ahead.
Show Notes:
(03:00) Why struggle and friction can be an advantage
(10:00) Curiosity, questions, and what "creation" really means
(16:10) Reframing mistakes and failure as fuel
(19:05) The operator pain behind EquipmentShare
(23:00) The jobsite moment that forced the idea into motion
(27:00) Inside Y Combinator and what Willy learned from the Silicon Valley bubble
(29:05) Building from Missouri and the meaning of "home"
(32:45) Constraint as a forcing function for scale, systems, and resilience
(35:25) Going public and what founders misunderstand about the shift
(38:10) Redbud VC and building an ecosystem close to home
(41:10) What Willy looks for in founders when success is still unproven
(46:05) Legacy, ritual, and the long game of creation
(48:00) Beyond the Bio: Willy Schlacks
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Willy Schlacks, Co-Founder & President, EquipmentShare
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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n this episode of Outsider Inc., host Ian Hathaway sits down with David Cohen, Co-Founder and CEO of Techstars, to unpack how a community-first mindset helped reshape what founder support can look like far beyond Silicon Valley. David traces his path from early founder wins and failures to building Techstars out of a small Boulder experiment rooted in mentorship and Give First. They discuss why networks and trust matter as much as capital, the hard tradeoffs that come with scale, and why David returned to the CEO seat with a renewed focus on quality, founder outcomes, and long-term community strength. Along the way, David breaks down his founder evaluation mantra, why teams beat ideas, what he believes most investors overvalue, and how to sustain a founder journey without losing yourself to it.
Show Notes:
(03:10) Community as the through line from the beginning
(08:25) Early computing and the power of networks
(12:40) First startup lessons and "unsucking" real problems
(16:35) Why Boulder and how place shaped the journey
(22:15) The moment networks became the unlock
(26:30) Building Techstars with mentorship and Give First
(31:50) Culture, scale, and why "better is better"
(37:05) How David evaluates founders: Team, team, team
(42:20) What most people overvalue in startups
(46:15) Founder mode, identity, and work life harmony
(52:30) Outsiders, underestimated founders, and why the model works
(57:10) Beyond the Bio: David Cohen
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: David Cohen, Co-Founder & CEO, Techstars
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com
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In this episode of Outsider Inc., host Ian Hathaway sits down with Hernán Kazah, co-founder of Mercado Libre and Managing Partner at Kaszek, to trace the outsider journey that helped put Latin America on the global tech map. Hernan reflects on growing up in Buenos Aires, the early lessons that shaped his resilience, and how his time at Procter & Gamble sharpened his appreciation for process and execution. After arriving at Stanford as an English learner, he caught the wave of the internet boom, met Marcos Galperin, and helped launch Mercado Libre in 1999. A moment when internet adoption in the region was near zero, capital was scarce, and there was no startup ecosystem to lean on.
Hernan walks through raising money in the dot-com window, surviving the crash by cutting marketing, doubling down on product and organic growth, reaching profitability in 2006, and ultimately taking Mercado Libre public in 2007. He then shares why he stepped away in 2011 to co-found Kaszek with a clear mission: bring early, high-conviction capital and real operator support to the next generation of Latin American founders. Along the way, he breaks down what he looks for in entrepreneurs and why building in emerging ecosystems often requires solving more than one problem at a time. We also dig into Kaszek's track record backing category-defining companies like Nubank, Creditas, QuintoAndar, and Kavak, and why Hernan remains bullish on the region's potential. His guiding principle is simple: move with conviction … or don't move at all.
Show Notes:
(06:55) P&G Lessons On Process
(11:10) Stanford Culture Shock
(16:34) Saying Yes To Mercado Libre
(20:08) Building In A No-Ecosystem Market
(23:55) Dotcom Crash And Capital Discipline
(29:05) IPO Validation And Profitability
(32:40) Leaving Mercado Libre
(33:47) Founding Kaszek
(42:07) What Kaszek Looks For
(46:18) Outsider Playbook in LatAm
(54:43) Legacy and Ecosystem Hopes
(57:21) Beyond the Bio with Hernan Kazah
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Hernan Kazah, Co-Founder, Mercado Libre & Managing Partner, Kaszek
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway sits down with Seth Levine, co-founder and longtime partner at Foundry, to explore a two-decade journey at the center of entrepreneurship, venture capital, and ecosystem building outside traditional power centers. Levine reflects on helping build Foundry into a top-tier venture firm based in Boulder, his belief in entrepreneurship as a driver of economic mobility, and the lessons behind his new book Capital Evolution. He also discusses backing overlooked founders, the philosophy of "give first," winding down Foundry by design, and his latest chapter launching Good Bread, a lending platform that expands access to capital for small business owners traditionally shut out of the financial system.
Show Notes:
(02:10) Why Entrepreneurship Fuels Job Creation and Innovation
(03:25) Capital Evolution and the Case for Dynamic Capitalism
(06:05) Long-Term Thinking vs. Short-Term Market Pressure
(08:45) Declining Economic Dynamism and Barriers to Opportunity
(12:00) Family Roots, Class Mobility, and Early Entrepreneurial Influence
(15:45) Lessons from the Dot-Com Boom, Bust, and Corporate Humility
(19:30) Entering Venture Capital After the Crash
(23:10) Founding Foundry and Betting on Non-Coastal Startups
(27:05) Backing Overlooked Founders and Scrappy Entrepreneurs
(31:40) Building a National Venture Platform from Boulder
(35:10) Deciding to Wind Down Foundry and Make Space for New Funds
(38:30) Writing The New Builders and Reframing Entrepreneurship
(41:30) Launching Good Bread to Expand Access to Small Business Capital
(45:45) What Makes Startup Ecosystems Resilient Around the World
(49:40) The Enduring Power of "Give First"
(54:00) Beyond the Bio: Seth Levine
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Seth Levine, Co-Founder of Foundry
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway interviews Gail Goodman, former CEO of Constant Contact. Goodman discusses her journey from her early entrepreneurial endeavors to leading Constant Contact from startup to IPO and ultimately to a $1.1 billion acquisition. She emphasizes the importance of execution over ideas and how a deep commitment to small businesses shaped her approach to building and scaling a SaaS company. She also reflects on the emotional transition after 17 years as CEO and her ongoing work supporting underrepresented entrepreneurs.
Show Notes:
(02:57) Childhood Entrepreneurial Roots
(06:59) Seeing Dysfunction Up Close and Learning What Not to Do
(08:03) The Leap to Leading Constant Contact
(12:09) Overcoming Imposter Syndrome and Building a CEO Peer Network
(18:59) Customer Research and the Art of "Following Them Home"
(21:13) Cracking Conversion and Retention in Early SaaS
(30:57) Preparing for an IPO and Leading Through Rapid Scale
(33:40) Public Company Pressures and Cultural Shifts
(36:00) The Emotional Reality of Transitioning Out of the CEO Role
(38:14) Joining Boards and Rethinking Leadership from a New Seat
(44:10) Being an Outsider in Tech and Venture Capital
(47:30) "People Gut" and the Art of Hiring Well
(51:55) Supporting Underrepresented Entrepreneurs Through EforAll
(54:00) Beyond the Bio: Gail Goodman
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Gail Goodman, Founder & CEO of Constant Contact
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway interviews Kyle Porter, founder and longtime CEO of SalesLoft. Kyle shares his remarkable journey from nearly failing in the first year of SalesLoft to scaling the company to unicorn status with a $2.3 billion valuation. He discusses the core principles of leadership, such as leading with love, staying mission-driven, and valuing corporate culture. Kyle also reveals personal challenges, including childhood health issues and a transformative college experience, and how these shaped his entrepreneurial path. Finally, Kyle talks about his current life on a tangerine farm and supporting his wife's business endeavors, emphasizing the importance of family and personal fulfillment.
Show Notes:
(02:12) Leading with Love: A CEO's Perspective
(02:55) Kyle's College Turning Point
(04:55) Childhood Hustles: The Seeds of Sales Passion
(06:52) Overcoming Childhood Health Challenges
(12:57) Early Professional Experiences and Lessons Learned
(15:51) The Birth and Rebirth of SalesLoft
(26:49) Navigating the Pandemic: Challenges and Growth
(30:41) Life Changes During the Pandemic
(31:31) The Vista Equity Acquisition
(34:31) Transitioning from CEO to Executive Chairman
(37:16) Supporting Each Other's Dreams
(44:04) Building SalesLoft in Atlanta
(51:08) Beyond the Bio with Kyle Porter
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Kyle Porter, Founder & fmr CEO of SendGrid
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway interviews Isaac Saldana, the co-founder and former CEO of SendGrid, and current CEO of Joy Labs. Isaac discusses the interplay of humility and confidence in leadership and shares his unconventional path to success. From being a non-English-speaking teenager who managed a family and two jobs at 19, to raising significant capital and guiding SendGrid to an IPO and a $2 billion acquisition by Twilio, Isaac reflects on the pivotal moments and decisions that shaped his career. He highlights the importance of grit, mentorship, and a values-driven approach to leadership. Isaac also touches on his current venture, Laneful, and the future of email communication infrastructure powered by AI.
Show Notes:
(10:42) The Entrepreneurial Spark: Rich Dad, Poor Dad
(14:21) The Birth of SendGrid: Solving Email Deliverability
(19:21) Navigating Early Success and Challenges
(23:33) A Pivotal Decision: Replacing Himself as CEO
(27:10) Scaling SendGrid to IPO
(30:41) Post-SendGrid: The Birth of Joy Labs
(32:40) Lane Four: Revolutionizing Email with AI
(35:34) Leadership and Values in Entrepreneurship
(42:42) Balancing Family and Ambition
(47:20) Beyond the Bio with Isaac Saldana
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Isaac Saldana, Co-Founder & fmr CEO of SendGrid
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., our guest is Aaron Slodov, co-founder of Remesh and co-founder and CEO of Atomic Industries. Aaron shares insights from his unique journey from a child tinkering in Cleveland to working at Google X, and founding a series of innovative companies. The discussion delves into the challenges and opportunities in American manufacturing, the impact of globalization, and the role of software and AI in modern industrial systems. Aaron also touches on his vision of re-industrializing America, his belief in tackling complex problems, and his leadership in fostering a new movement through the Re-Industrialize Summit and the New American Industrial Alliance.
Show Notes:
(04:34) The Formative Years: From Cleveland to Google
(11:23) The Birth of Remesh: A Social Experiment
(15:09) Challenges and Lessons from Remesh
(18:00) A New Beginning: The Genesis of Atomic Industries
(20:36) The Flaws in Global Manufacturing
(24:10) Building a Testbed Factory in Detroit
(26:21) Merging Software with Physical Production
(30:23) Scaling a Movement: Reindustrialize
(33:26) Encouraging Talent in Hard Tech
(36:00) Personal Insights and Reflections
(40:01) Beyond the Bio with Aaron Slodov
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Aaron Slodov, Co-Founder & CEO, Atomic Industries
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway interviews Guillaume de Zwirek, founder and CEO of Artera. Guillaume's journey from a classical guitarist and world-class Ironman triathlete to a successful health tech entrepreneur is anything but conventional. Inspired by his personal frustrations as a healthcare patient, Gui founded Artera, a platform that unifies patient communication. Through his story of quitting a comfortable job, securing funds from friends, and unwavering determination, Gui illustrates the concept of 'burning the ships' with no retreat. The interview delves into his experiences at Google and data platform Graphiq, the decision to move Artera to Santa Barbara, and the challenges faced during the COVID-19 pandemic. Gui also shares his views on leadership, the impact of AI on healthcare, and future goals for Artera.
Show Notes:
(02:20) From Ironman to Healthcare Innovator
(06:40) Early Life and Entrepreneurial Spirit
(11:28) The Google Experience
(16:23) Joining Graphic and the Santa Barbara Move
(28:15) Choosing the Right Business Partners
(29:50) The Joy of Building and Learning
(30:37) A Bold Move to Santa Barbara
(35:43) Embracing AI and Future Challenges
(40:32) Leadership and Personal Growth
(48:10) Final Reflections and Advice
(49:30 Beyond the Bio with Guillaume de Zwirek
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Guillaume de Zwirek, Founder & CEO, Artera
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway speaks with Jon Lensing, co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. From growing up in rural Iowa to training as a surgeon, Jon's path took an unconventional turn when he left medicine to build a company addressing healthcare access. Since its founding in 2020, OpenLoop has scaled to more than 2 million patients annually, raised over $120 million, and reached unicorn status while staying rooted in Iowa. Jon shares how constraint breeds creativity, the scrappy early days writing letters to doctors in a grocery store café, and the near-collapse when a term sheet fell through the night before payroll. He also reflects on co-founder dynamics, the lessons of a major pandemic pivot, building a fire-eating culture, and why success stories in outsider places fuel the next generation of founders.
Show Notes:
(07:42) Medical school, entrepreneurial sparks, and building side businesses
(12:06) The decision to forgo residency and launch OpenLoop
(14:03) Scrappy early days: handwritten letters, Hy-Vee café, and Techstars Iowa
(18:00) Capital constraints, rejections, and why scarcity fueled efficiency
(20:01) Meeting co-founder Christian Williams and complementary dynamics
(22:16) Making a high-stakes pandemic pivot into telehealth infrastructure
(28:14) A pulled term sheet, payroll crisis, and lessons on choosing investors
(33:02) Building a "fire-eating" culture and hiring for high-output operators
(38:12) Why Jon chose to build in Iowa and the advantages of staying close to customers
(45:55) Beyond the Bio with Jon Lensing
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Jon Lensing, Co-Founder & CEO, OpenLoop
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway speaks with Jimena Pardo, co-founder of Carrot, Mexico's first car-sharing platform, and now Co-Founder & Managing Partner at Hi Ventures. Jimena opens up about the rollercoaster of building Carrot, the lessons of operating in a tough market, and how she transitioned from founder to investor. She shares candid reflections on founder identity, resilience after burnout, and her vision for Latin America as a launchpad for globally recognized startups. From raising capital in an emerging market to shaping Hi Ventures into a firm that champions bold, outsider entrepreneurs, Jimena's journey is a masterclass in grit, adaptation, and long-term vision.
Show Notes:
(03:18) Early ambitions, education, and what drew Jimena into entrepreneurship
(07:42) Founding Carrot and tackling mobility challenges in Mexico
(15:33) Lessons from scaling Carrot and navigating the exit
(22:06) The personal toll of entrepreneurship and founder burnout
(29:47) Transitioning from founder to investor and joining Meta
(36:21) The importance of founder identity beyond the startup
(43:18) Launching Hi Ventures and its mission to back bold entrepreneurs
(52:04) Breaking capital barriers in Latin America and building global companies
(1:01:19) Why transparency, humility, and mentorship matter in entrepreneurship
(1:09:33) Jimena's vision for the next generation of founders in Latin America
(1:16:55) Beyond the Bio with Jimena Pardo
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Jimena Pardo, Co-Founder of Carrot & Co-Founder and Managing Parter at Hi Ventures
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway chats with Melodie van der Baan, co-founder and CEO of Max Retail. Melodie shares her unconventional journey from skipping college to diving into real estate, losing everything in the housing crash, and then transforming into a mobile designer clothes distributor. Her challenges and experiences eventually led her to start Max Retail, a platform for converting unsold inventory into revenue, which now serves over 2,000 retailers across the U.S. The discussion highlights her perseverance, customer focus, and innovative approach to the retail industry.
Show Notes:
(02:41) Skipping college and diving into real estate as a teen
(05:22) Losing everything in the housing crash
(08:14) Life on the road: selling designer clothes from a Sprinter van
(12:49) Launching a retail shop and confronting the inventory problem
(18:56) Starting Max Retail during the pandemic
(25:03) Breaking into Techstars after multiple attempts
(32:17) Scaling to 2,000+ retailers and raising $20M+
(41:09) Lessons on persistence, resilience, and customer focus
(47:56) Beyond the Bio with Melodie van der Baan
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Melodie van der Baan, Co-Founder & CEO of Max Retail
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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In this episode of Outsider Inc., host Ian Hathaway interviews Jewel Burke Solomon, a founder, investor, and community leader based in Atlanta. Jewel shares her experiences of co-founding PartPic, a startup designed to identify and replace industrial parts through visual search technology, which was later acquired by Amazon. She discusses her challenges in raising capital as a black female founder and how those experiences inspired her to become an investor. Jewel highlights her work at Google for Startups, where she helped launch the Black Founders Fund and Latino Founders Fund. She also talks about co-founding Collab Capital, a venture fund focused on building long-term wealth and trust in underserved communities. This is a story of turning hard-earned lessons into purposeful action and reimagining who gets backed in venture.
Show Notes:
(01:17) Jewel's Journey with PartPic
(06:27) Navigating Identity and Overcoming Bias
(10:16) Early Influences and Entrepreneurial Roots
(15:00) From Google to McMaster Car
(20:25) The Birth of PartPic
(27:28) The Decision to Sell to Amazon
(30:26) Handling Post-Sale Depression
(36:55) Founding Collab Capital
(38:37) The Atlanta Startup Ecosystem
(40:23) Mental Health Initiatives at Collab
(42:10) Reflections on DEI and Future Goals
(48:15) Beyond the Bio with Jewel Burks Solomon
✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC
✅ Guest: Jewel Burks Solomon, Co-Founder of Partpic & Managing Partner, Collab Capital
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
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