One founder. One real conversation. 30–50 minutes on what it actually took to build, raise, and scale.
57+
Episodes
30–50
Minutes each
1
Founder per episode
All Episodes
Nelson Brooks
Founder & CEO, Cabana Boys Events
Nelson Brooks spotted an untapped market at a bachelorette party, launched Cabana Boys Events in August 2020 during COVID, scaled to 10 US markets under 6 brands, and secured a Shark Tank deal with investor Kendra Scott. He breaks down why charisma, not appearance, is the only thing that scales in hospitality.
Alex Jekowski
Founder & CEO, Cents
Alex Jekowski left college sophomore year, exited his first startup, then stumbled into laundromats and built Cents into a vertical SaaS platform that raised nearly $250M including a $140M Series C. He shares the fundraise that nearly broke him and why betting on hardware when investors said no became a lasting competitive moat.
Dr. Michael Filosi
Exited Founder, Fullarton Park Dental
Dr. Michael Filosi bought a run-down two-chair dental practice nobody wanted and scaled it into the largest clinic in Adelaide before a private equity exit with four firms competing to acquire. He shares his hiring strategy, a flawless Google review program, and why he walked away at 42 when the reward of building disappeared.
Christof Gomez Mannfeld
Founder, solvee
Christof Gomez Mannfeld spent seven years at Bosch in automotive machine learning, was let go, then moved his family to southern Spain to build solvee — an AI accelerator that learns a founder's specific business through 43 structured steps. He makes the case for AI that interrogates rather than hallucinates.
Florian Kemmerich
Founder, Vocating AI · Impact Investor
Florian Kemmerich was on track for the Barcelona Olympics in judo, spent 15 years in corporate healthcare, then had a single coaching session at 33 that triggered a pivot to impact investing across 100+ companies in 30+ countries. He built Vocating AI to help millions of young people find their vocation before AI eliminates the entry-level jobs that used to teach it.
Cody Graham
COO, SoGo
Cody walks through the mindset shifts required to move from corporate operator to startup builder, covering AI integration, building community-driven products, and why the best founders stay deliberately uncomfortable.
Steve Ramona
Founder & Podcast Host
Steve breaks down his ASLA framework: Ask, Listen, Learn, Act — and demonstrates how authentic networking can turn a casual conversation into a long-term business relationship. One of the most practical episodes on relationship capital we've recorded.
Iliana Alvarado
Founder, XPERTEKIT.Inc
Iliana built a tech venture across three countries after a career defined by embracing the unpredictable, from odd jobs to international roles. She makes a compelling case that cultural agility is the most underrated founder skill.
Sharon Gai
Former Alibaba Executive & Keynote Speaker
Sharon went from leading Alibaba's global growth to building her own personal brand, and discovered that documenting failures outperforms polished success stories. She shares the counterintuitive rules of digital presence and why AI is the great equalizer for solo founders.
Russell Breuer
Founder, Spot & Tango
Russell left management consulting to cook dog food in his apartment. Nine figures later, Spot & Tango is one of the fastest-growing DTC pet brands in the country. He breaks down the direct-to-consumer playbook and the bet on personalized nutrition that changed everything.
Gadareth Higgs
Investment Analyst, Grander
Gadareth went from the Bahamas to Yale to the front lines of life sciences investing, and shares how he evaluates early-stage biomedical companies, why continuous improvement is his operating system, and how AI is reshaping the due diligence process.
Robie Webster Jr.
Founder, Mtrc
Former Division I athlete Robie Webster Jr. turned the discipline of competitive sport into a fitness technology company. He talks about finding a co-founder, the grit it takes to build without a safety net, and why learning never stops for a first-time founder.
Chris Tsakalakis
Former CEO, StubHub · Venture Partner, Starhawk
Chris ran one of the most recognizable B2C marketplaces in the world before pivoting to venture. He traces the lessons from Bain to StubHub, the aggressive marketing bets that paid off, and why he believes AI's impact on business will be bigger than the internet.
Chris Yeh
Co-Author, Blitzscaling · Investor & Speaker
Chris co-wrote the book on blitzscaling with Reid Hoffman, and in this episode he goes deeper on what actually separates companies that scale from those that plateau. He covers conviction, lifelong learning, and building the kind of collaborative network that compounds over decades.
Andrew Ackerman
Two-Time Exit Founder & Author
Andrew has navigated two startup exits and written a book about it. He shares the resilience frameworks that got him through the hard parts, the mental models he wishes he'd had earlier, and what he tells first-time founders who are just starting to feel the pressure.
Frances Pratt
Founder & CEO, Metisan
Frances built a sales consulting firm for founders who are brilliant at their craft but uncomfortable in the room. She explains why most selling fails at listening, how storytelling closes deals that decks can't, and the community-building strategies that create revenue without cold outreach.
Aya Kikimova
Founder & Former Microsoft
Aya left the stability of Microsoft to build from scratch, and she's honest about how different the two worlds are. She maps the psychological and operational challenges of the transition, the obstacles she didn't see coming, and how she found her footing as a first-time solo founder.
Michael Ceely
Executive Coach & Former Pro Cyclist
Michael Ceely is a former professional cyclist who discovered that the mental frameworks behind winning races apply directly to running a business. He walks through the performance methodology he developed coaching executives and why most leaders are missing the discipline that elite athletes train daily.
Elise Madrick
Founder & CEO, Cerenè
Elise Madrick left executive education at Kellogg after her own international journey revealed the difference between incremental change and genuine transformation. She founded Cerenè, a 108-day immersive program in Morocco and France, recognizing that no amount of habit-stacking at home disrupts all four contexts of change simultaneously.
Logan Burchett
Founder & CEO, Forecastr
Logan Burchett built Forecastr to give early-stage startups the financial modeling tools that were previously only available inside big companies. He shares how better financial visibility changes the decisions founders make and what he learned about building B2B software for a customer segment that hates spreadsheets.
Aaron James Yeager
Founder & Creative Entrepreneur
Aaron James Yeager built a business at the intersection of music, lifestyle, and entrepreneurship, using creative platforms as a launchpad for brand building. He shares the unconventional path that got him there and what he learned about building at the edge of culture and commerce.
Alex Bean
Co-Founder, Divvy · Tandem Invest
Alex Bean co-founded Divvy, combined corporate cards with expense management software, and sold it to Bill.com in one of fintech's landmark acquisitions before the product was fully built. He now backs early-stage founders at Tandem Invest, applying what he learned about conviction, culture, and selling before you're ready.
Chris Riklin
Co-Founder, Topline
Chris Riklin spent over a decade at NationBuilder watching talented professionals lose opportunities to outdated hiring systems, then co-founded Topline, a marketplace where fractional executives win on results, not relationships. He shares how a serendipitous co-founder alignment became the foundation of the company.
Josh Cain
Founder & BCI Researcher
Josh Cain is working at the frontier of brain-computer interfaces, one of the most consequential emerging technologies of the next decade. He explains the current state of BCI development, the regulatory landscape, and what founders in adjacent spaces need to understand about where this technology is heading.
Luke Ashenbrand
Founder, Emblem
Luke Ashenbrand returns to Start to Scale with an update on Emblem, the company he has been building since his first appearance on episode 3. He shares what has changed, what building has taught him, and how manifesting a business vision into an operating company is harder and more rewarding than he expected.
Anika Gakovic
Executive Coach & Founder
Anika Gakovic made the transition from a structured corporate career to building her own executive coaching practice, helping leaders unlock clarity they couldn't find inside traditional organizations. She shares what the identity shift required, how she built a client base from scratch, and what most corporate executives misunderstand about the founder path.
Orly Zeewy
Brand Strategist & Author
Orly Zeewy has spent her career helping early-stage startups move from fuzzy positioning to sharp, differentiated messaging that actually closes deals. She shares the frameworks she uses to get founders to articulate what they do and why it matters, and why so many smart companies fail at the basics of brand.
Sanjay Goel
Founder & CEO, NachoNacho
Sanjay Goel is the founder and CEO of NachoNacho, a SaaS subscription management platform helping companies discover, track, and optimize the software they already pay for. He walks through the company's founding thesis, the market dynamics driving SaaS sprawl, and what growing a B2B product requires that most founders underestimate.
Ryan Hughes
Founder, Fan Pier Labs
Ryan Hughes used Northeastern's co-op program to get inside Google and Snapchat before graduating, observing what scale does to engineering speed and what a post-IPO culture shift looks like from inside. He left to found Fan Pier Labs, an AI-driven software consultancy helping early-stage startups build faster.
John Graham
Founder, The Giraffe Heroes Project
John Graham spent decades in diplomatic roles before founding The Giraffe Heroes Project, which identifies and celebrates people who stick their necks out for the common good. He shares what a career in diplomacy teaches you about leadership, courage, and why most organizations fail to reward the people doing the most important work.
Amit Guruprasad
Founder & CvO, Devan MedTech Solutions
Amit Guruprasad is building technology for the healthcare sector with a focus on tools that actually reach clinicians and patients. He shares the unique challenges of selling into healthcare, navigating regulatory environments, and building a company in a sector where the stakes are literally life and death.
Nathan Beckord
Founder & CEO, Foundersuite · Fundingstack
Nathan Beckord has worked with thousands of founders raising capital through Foundersuite and Fundingstack, observing patterns across successful and unsuccessful fundraises from a rare vantage point. He shares what investors actually respond to, how the fundraising process has evolved, and the one thing most founders skip that costs them the deal.
Aytekin Tank
Founder & CEO, Jotform
Aytekin Tank bootstrapped Jotform from a school computer in Turkey to 25 million users and 600 employees without a single dollar of venture capital, competing directly against Google Forms. He shares his 50/50 product-and-growth rule, why the free tier is a feedback engine, and how long-term thinking beats chasing the next round.
Mike Reilly
Founder, Poached to Perfection
Mike Reilly is the founder of Poached to Perfection, building a focused culinary concept with a clear thesis about where consumer tastes are heading. He shares the realities of building in food and beverage, what it takes to validate a concept before you scale it, and what most founders get wrong about product-market fit in consumer.
John Kennelly
Founder, Speaker & Multi-Exit Operator
John Kennelly has been through multiple startup cycles and an exit, giving him a view of the founder journey that spans the early hustle and the negotiation table. He shares frameworks for thinking about exits early, how to command a room when it matters, and the communication skills that separate founders who close from those who don't.
Zach Beegal
Founder & Performance Coach
Zach Beegal built his career navigating high-pressure environments and the psychological demands of performance under scrutiny, developing a philosophy around fueling success without burning out. He shares what he has learned about pressure, resilience, and why the mental side of building a company is the last thing most founders invest in until it is the only thing that matters.
Daniel Blumin
Founder & CEO
Daniel Blumin is a founder and operator who shares how he built his company, the strategic decisions that shaped its growth, and the mindset required to run a business that depends on constant iteration and customer feedback. He brings a perspective shaped by both creative instinct and hard-nosed operational thinking.
Carol Palombini
Founder & Clinical Psychologist
Carol Palombini built her career across two countries and two disciplines, moving from clinical psychology in Brazil to entrepreneurship in Portugal. She shares how her background in psychology informs how she builds, leads, and connects with customers, and what the cross-cultural experience of building in Europe has taught her.
Brittany Fowler
Executive Coach & Founder
Brittany Fowler left a career in education to become an executive coach, discovering that the skills that made her an exceptional teacher, clarity, empathy, and structured feedback, are exactly what leaders need most. She walks through her transition, how she built her coaching practice, and why the best coaches are always the ones who have been in the rooms they are advising.
Andy Karuza
Marketing Leader & Entrepreneur
Andy Karuza is a marketing leader and entrepreneur who has built brand and growth programs for companies at multiple stages, with a track record in both B2B and consumer markets. He shares his philosophy on what marketing actually is, when to invest in brand versus performance, and what he has learned from watching too many startups optimize for the wrong metrics.
John Olson
Entrepreneur & Executive Coach
John Olson managed healthcare teams overseeing a billion-dollar budget before leaving to build an e-commerce business, a real estate portfolio, and an executive coaching practice simultaneously. He shares his 'Who Not How' delegation framework and why peer groups consistently deliver the highest ROI of any leadership investment.
Mike Spidaliere
CEO, First Time Founder Capital
Mike Spidaliere is the CEO of First Time Founder Capital, a fund specifically designed to back first-time founders who lack the track record most investors require. He explains the thesis behind the fund, what he looks for when conventional investor signals are absent, and what he has learned from backing founders at the earliest and most uncertain stage of company building.
David Adeleke
Founder & Fintech Operator
David Adeleke is working at the frontier of fintech in Africa, building infrastructure that serves populations that traditional financial systems have historically excluded. He shares the unique challenges and opportunities of fintech in Africa, what building for a rapidly growing market looks like from the inside, and why the lessons from African fintech apply far beyond the continent.
James Corwin
Wildlife Artist & Founder, Corwin Galleries
James Corwin grew up in Montana, won an unexpected art scholarship, and spent summers selling miniature paintings at farmers markets before scaling into Corwin Galleries. An African safari redirected his focus to wildlife art, and mastering Facebook ads turned a studio practice into a multi-venue business.
Fritz Lanman
CEO, ClassPass & Mindbody
Fritz Lanman led Microsoft's $240M strategic investment in Facebook before becoming CEO of ClassPass, raising a $285M Series E and achieving unicorn status. He traces what big tech teaches you about infrastructure, why capital is a tool not a trophy, and the Montana office that became the company's largest.
John Ignacio
Founder & Former NYC Teacher
John Ignacio left a teaching career in New York City and moved to Manila to build a startup from scratch, navigating a completely new market, culture, and entrepreneurial ecosystem. He shares what the move taught him, the specific advantages of building in Southeast Asia, and how a background in education turned out to be a genuine edge in company building.
Sher Downing
Founder & Former Educator
Sher Downing moved from a career in education into entrepreneurship, applying the skills she developed teaching and building programs to the challenges of building a company from scratch. She shares the mindset required to make that transition, what surprised her most about the founder's journey, and what she would do differently if she were starting again.
Chase Brignac
Founder, ChatOpenSource · Y Combinator
Chase Brignac grew up in Louisiana's Cancer Alley, worked on NASA's Curiosity and Maven Mars missions, and scaled Deliv from zero to a million deliveries per day before its Target acquisition. He then founded ChatOpenSource through Y Combinator, an open-source enterprise AI alternative built for organizations with strict data privacy requirements.
Toni Witt
Community Builder & Founder
Toni Witt explores what it means to build a life and a network in a completely new place, without the social infrastructure most people take for granted, and how that experience maps directly onto the founder's journey. She shares what intentional community-building looks like and how founders can apply the same principles to build environments where the best people want to stay.
Diana Stepner
Product Leader & Advisor
Diana Stepner has spent her career at the intersection of product leadership and organizational design, working across Silicon Valley and London and advising companies on how great products actually get built inside complex teams. She shares what separates product teams that ship from those that debate, and what great product leadership looks like in practice.
Ranjodh Singh
Founder & Entrepreneur
Ranjodh Singh explores the intersection of spirituality, economics, and technology in modern India, one of the most complex and rapidly changing societies on the planet. He shares how ancient frameworks of meaning interact with modern market forces and what the rest of the world misunderstands about India's development trajectory.
Melissa Kwan
Founder & Bootstrapped Operator
Melissa Kwan bootstrapped her business to significant scale without venture capital and has become one of the clearest voices on why raising money is not always the right answer. She breaks down the real tradeoffs between bootstrapping and fundraising, what each approach demands, what it costs, and how to know which path is right for your specific business.
Armando Vera Carvajal
Co-Founder & CEO, Hangtight
Armando Vera Carvajal immigrated from Mexico at four, was rejected twice by UT Austin's business school, studied in Paris and Singapore, trekked the Peruvian Amazon, then built Hangtight, an AI social planning app that acquired a competitor to accelerate growth. He credits his parents' sacrifice as the reason quitting was never an option.
John Lionberger
Engineer, Entrepreneur & Pro Racing Driver
John Lionberger went from working rock concerts and Broadway productions to electrical engineering, then built a regional consulting office from $0 to nearly $500M in revenue while racing competitively on weekends. He shares lessons from an ESOP transition, a front-row seat to an IPO, and why racing makes you a sharper business operator.
Luke Ashenbrand
Startup Consultant & Founder
Luke Ashenbrand was a Princeton Division I football lineman whose career ended with a traumatic concussion that left him unconscious for a month. He channeled that setback into startup consulting, applying the same resilience to early-stage ventures and sharing what building Vega during COVID taught him about shipping under pressure.
Robyn Hobson
VP of Marketing, Remote Vans
Robyn Hobson built a 13-year marketing career across South Africa, China, and the US, from mobile tech startup exits to crisis communications at a low-cost airline and growing Woolworths SA to 500,000 social followers. She shares what cross-cultural experience teaches you about brand that no playbook can.
Taiga Gamell
Founder, Gildre
Gildre founder Taiga Gamell introduces Start to Scale: the podcast about founders who have done it, raised capital, scaled companies, and learned what actually works. He sets the stage for the conversations ahead and explains why real founder stories told honestly are the most valuable resource an early-stage builder can access.
Be on the show
We only record with founders who have real reps — a raise, an exit, a lesson hard-earned. If that's you, reach out.
Pitch yourself as a guestStart to Scale is produced by Gildre. New episodes drop monthly.