Ready, Set, Startup! - Strategies from Founders, Funders, and Beyond

Aya Jacob, a business psychologist researching connected leadership, believes most founders misunderstand what actually makes them effective under pressure. After a decade in high-stress digital marketing, she saw how a leader’s internal chaos quietly ripples through a team, shaping trust, performance, and culture. That experience led her to study the link between self-connection and leadership im...

Artem Kuzmych, co-founder of Applica, went from freelancing in marketing to building a philosophy-infused mental health app that started scaling fast, until the App Store suddenly removed it and he spent the next two years fighting to get it back. That chaos forced a pivot that shaped everything he does now. Artem now helps mobile app founders grow with a full-cycle approach that goes way beyond p...

Jim Ryun went from getting cut from nearly every team to becoming the first high schooler in history to break four minutes in the mile. He credits much of that breakthrough to a coach who convinced him to adopt a dream he did not yet believe was possible, and to a moment when he decided to take ownership of it himself. That shift carried him beyond track into small business, public service in Cong...

Leah Ellis, founder of the Society of Child Entrepreneurs, is building a nonprofit that teaches kids ages 6 to 17 entrepreneurship, financial literacy, and leadership by making it real. Kids launch actual businesses, sell at children’s business fairs, and then workshop what worked and what didn’t so they can iterate and grow. She traces her own entrepreneurial streak from selling five-dollar MySpa...

Marcio Goncalves, founder of a fast-growing virtual assistant agency (a team that handles admin and day-to-day tasks for busy founders) and a fully remote podcast production company, argues that scale comes from structure, not luck. He shares how his first taste of entrepreneurship started at 12, raising pet-store hamsters and finding homes for the new litters, and how that early instinct evolved...

Matthew Stafford, professional investor and co-founder of Nine Others, argues that simplicity wins. He shares how starting on the Venture Capitalist side sharpened his founder's empathy, the early signals he listens for, and how one dinner became a global peer network. We unpack the pre-boom London fundraising scene, practical ways to cut noise from your pitch, and the community mechanics that act...

Cheryl Kellond has built startups from the ground up, survived the crash of a hardware business, raised millions in venture capital, and walked away with battle scars. In this episode, she pulls back the curtain on what it really takes to lead a company through chaos. We get into why hiring fast can backfire, how funding can trap you, and what founders often overlook when chasing growth. Cheryl ta...

Jesse Mecham, former accountant and creator of You Need A Budget, argues that your real money problem is worry, not math. He shares how a tiny spreadsheet he built to fix one household cash crunch became a calm, profitable business, and what he learned from building his software and methodology: YNAB (You Need A Budget) at night while working full time, botched early hires, and the moment he stopp...

Reuben Levinsohn, professional investor and founder coach behind Exit Quotient Ventures and Flying with Founders, argues that clarity and discipline win. He shares how starting from an “exit first” mindset sharpens founder focus, the early signals he listens for like EQ, leadership quotient, paid pilots, and a clean path to $1M ARR, and when to graduate beyond founder-led sales. We unpack the red...

Jule Salem turned a panicked request to staff 200 call-center reps into the foundation of Salem Solutions. In this episode she shares how “smiling and dialing” became a scalable system, why call centers require highly skilled technical talent, and the playbook she uses to fill high-volume roles without sacrificing quality. You’ll hear her early scrappy origins, the mindset that converts urgent pro...

Dawn Haynes is the CEO of Stardust Studio, a nonprofit accelerator for early-stage tech startups. In this episode, Dawn shares her journey from pioneering transatlantic leisure travel to leading a team focused on helping founders build scalable, sustainable businesses. She discusses the importance of problem-solving, resilience, and embracing feedback, along with the challenges of finding the righ...

Marc and Gina Calaunan built Healing Hands from a love story into eight thriving clinics. They reveal the scrappy moves that sparked their first surge, the “four clinic wall” that almost broke them, and the systems that protected quality while they scaled across borders. Expect hard-won playbooks on hiring for heart, SOPs that actually stick, and the mindset that kept their marriage strong while t...

What happens when you jump into entrepreneurship without a co-founder and without a safety net? Vijay Rajendran has done just that, and more. In this episode, he shares his journey from launching Hungry Globetrotter to leading digital innovation at global banks and advising hundreds of startups. We dig into the emotional weight of solo founding, the value of structured support, and why your “path...

Doug Polster was deep into clinical work when a conversation with a former classmate sparked something bigger. What started as a way to keep his private practice afloat during COVID slowly turned into a cross-state mental health network rooted in accessibility and real care. In this episode, Doug unpacks the lessons behind Thriving Center of Psychology’s growth, from sunsetting a failed tech platf...

Stavros Michailidis didn’t plan to become a founder. He simply grew up around it. From revitalizing his family’s construction business to landing Fortune 500 clients with an innovation consultancy, his path has been shaped by experimentation, reinvention, and a deep curiosity about what makes businesses actually work. In this episode, he reflects on the difference between an A-plus idea and a B-pl...

What if your biggest success came from a total collapse? For Ryan Estes, that moment came when the pandemic wiped out his agency’s entire client list. Instead of folding, he doubled down on a side project—Kitcaster—and turned it into a thriving podcast booking service that would eventually be acquired. In this episode, Ryan opens up about his scrappy start, the mindset shift that fueled his growth...

After years of side hustles and self-doubt, Steve Young made one decision that changed everything. He began his entrepreneurial journey selling cassette tapes in grade school, but it wasn’t until he launched a niche podcast about apps that things finally clicked. In this episode, Steve shares how fear nearly held him back, how he landed his first client, and how he built a profitable agency withou...

When Chris Girbés left a steady job to start his own wealth practice, he wasn’t chasing scale. He was chasing meaning. In this episode, he shares what he’s learned from working with startup founders: the myth of the perfect exit, the danger of unclear goals, and the burnout that comes from tying your identity too closely to your business. Whether you're scaling or still scrappy, this conversation...

When Erik Stanley left the comfort of a steady paycheck and the familiarity of a running store, he didn’t just launch a business, he built a movement. In this episode, Erik shares how Trail Roots was born from a desire to coach differently, build genuine community, and carve out space on Austin’s untamed trails. He opens up about the emotional hurdles of breaking ties, the real cost of hiring wron...

At just 25, Tom Williams launched his first lending business with $5,000, a dream, and a San Francisco office he secretly lived in. In this episode, Tom walks us through his unorthodox journey from boat-washing teenager to fintech founder, revealing the pivotal moments, early sacrifices, and bets that shaped his entrepreneurial path. He opens up about navigating failure, weathering the dot-com bus...

Neil Cameron’s entrepreneurial journey didn’t start in a boardroom—it started on a beach in Australia after a career in athletics came to an unexpected end. In this episode, Neil reflects on the leap from solo founder to seasoned leader, revealing the struggles of bootstrapping, the power of listening to your customers, and the hard-earned wisdom behind building the right team. With honesty and hu...

When Tiffany Bailey stepped into her family’s sod farming business, she didn’t see herself as an entrepreneur, just someone grinding to get the work done. But nearly two decades later, she’s redefined the company, the culture, and herself as a leader. In this episode, Tiffany shares the raw truth about running and growing a business with family: the trust, the tension, and the tough calls. Hear ho...

Can a robot become your child’s best friend? Peter Fitzpatrick thinks so. In this episode, Peter, co-founder of Fawn Friends, shares the personal story that led him to build emotionally intelligent AI companions for kids. From pool party hustles in grade school to raising millions in venture capital, Peter opens up about the emotional challenges of leadership, the power of character-driven product...

What happens when someone who loves being the #2 decides to take the lead? Bryan Barletta, founder of Sounds Profitable, joins the show to talk about his unlikely journey to building one of the most influential organizations in podcasting. From calling out broken systems to creating real solutions, Bryan shares how he’s challenging industry norms, creating momentum without investors, and building...

Iñaki joins the show to share how he turned a no-code prototype and one powerful ally into his fast-growing climate-tech startup, Climatta. He dives into the power of starting lean, why building with customer feedback is everything, and how trust—not just traction—wins investors. From co-founder dynamics to bootstrapping with nothing but a Figma file and a favor, this is a raw, insightful look at...