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

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

Let’s pull back the curtain on what really goes down in the Startup world. Every episode offers honest, off-the-cuff chats with founders, investors, analysts, and other Startup insiders as they share the hard-earned wisdom you can't find in a business textbook. We break down the wins, the disasters, the risky bets, and the lessons learned along the way, delivered with zero intimidation and a lot of practical takeaways. If you’re building, dreaming, or just curious about how Startups actually work, you’re in the right place. Ready? Set…let’s get STARTed!

Episodes

Nothing About Us Without Us: Teaching Kids Leadership Through Ownership w/ Leah K. Ellis of The Society of Child Entrepreneurs

March 2, 2026 • 40 mins
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 MySpace layouts in high school to runnin...
Mark as Played

How Data-Informed Structure Can Turn Chaos Into Scalable Growth w/ Marcio Goncalves of WiseVAs

February 16, 2026 • 46 mins
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 into launching a podcast in 2012 be...
Mark as Played

Simplicity Wins: Inside the Mind of a Professional Investor w/ Matthew Stafford

February 2, 2026 • 48 mins
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 actually move founders forward. --- ...
Mark as Played

Finding Your Funding Fit w/ Cheryl Kellond of Play Money Studios

January 19, 2026 • 52 mins
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 talks candidly about ignoring her gut...
Mark as Played

When Core Values Beat Venture Capital: Building a Bootstrapped Business w/ Jesse Mecham of YNAB

January 5, 2026 • 56 mins
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 stopped playing small. We unpack the myt...
Mark as Played

Healthy Founders, Healthy Exits: The Human Side of Startup Success w/ Reuben Levinsohn of Washington Advisors & Ventures

December 22, 2025 • 36 mins
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 flags that kill momentum, practical...
Mark as Played

Smiling, Dialing, and Scaling: Building a Staffing Agency for Call Centers w/ Jule Salem of Salem Solutions

December 8, 2025 • 40 mins
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 problems into opportunity, and practic...
Mark as Played

Inside the Entrepreneurial Mind: What Successful Founders Do Differently w/ Dawn Haynes of Starter Studio

November 24, 2025 • 48 mins
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 right co-founders and navigating the wo...
Mark as Played

Serve First, Scale Second: How to Turn Passion Into Purpose w/ Marc & Gina Calaunan of Healing Hands

November 10, 2025 • 44 mins
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 the business leveled up. If you are ...
Mark as Played

The Founder’s Focus: Culture, Capital, & Conviction w/ Vijay Rajendran of Startup System

October 27, 2025 • 42 mins
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 to moat” matters more than having o...
Mark as Played

Therapy Without Compromise: A Founder’s Fight for Quality Care w/ Doug Polster of Thriving Center of Psychology

October 13, 2025 • 45 mins
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 platform to rethinking how founders defi...
Mark as Played

Getting Out of Your Own Way: Unlocking Your Impact w/ Stavros Michailidis

September 29, 2025 • 50 mins
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-plus outcome, why most hiring mistake...
Mark as Played

Built to Sell: How to Scale with Exit Intention w/ Ryan Estes of Kitcaster

September 15, 2025 • 38 mins
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, and why building a culture rooted...
Mark as Played

Content is the Cheat Code: an Organic Growth Playbook w/ Steve Young of App Masters

September 1, 2025 • 35 mins
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 without outside funding. It's a story abo...
Mark as Played

Founder Finances: Wealth, Life, & the Meaning of “Enough” w/ Chris Girbés of Five Oceans Advisors

August 18, 2025 • 53 mins
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 is packed with grounded insight on ...
Mark as Played

Building with Purpose: Lessons for the Long Run w/ Erik Stanley of Trail Roots

August 4, 2025 • 46 mins
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 wrong, the power of purpose, and why ha...
Mark as Played

The Intuition Advantage: Using Gut and Grit to Bet Big and Bounce Back w/ Tom Williams of ELEASE

July 21, 2025 • 54 mins
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 bust from inside Silicon Valley, and r...
Mark as Played

From Long Jump to Leap of Faith: Starting Solo and Scaling Smart w/ Neil Cameron of Sport Works

July 7, 2025 • 40 mins
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 humility, he shares what it really ta...
Mark as Played

Betting the Farm: Navigating the Risks & Rewards of Family Business w/ Tiffany Bailey of Bayside Sod

June 23, 2025 • 55 mins
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 how she navigated succession, scaled ...
Mark as Played

Can AI Give Our Kids Emotionally Intelligent Friends? w/ Peter Fitzpatrick of Fawn Friends

June 16, 2025 • 37 mins
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 products, and why putting truth first migh...
Mark as Played

Popular Podcasts

    Betrayal Season 5

    Betrayal Season 5

    Saskia Inwood woke up one morning, knowing her life would never be the same. The night before, she learned the unimaginable – that the husband she knew in the light of day was a different person after dark. This season unpacks Saskia’s discovery of her husband’s secret life and her fight to bring him to justice. Along the way, we expose a crime that is just coming to light. This is also a story about the myth of the “perfect victim:” who gets believed, who gets doubted, and why. We follow Saskia as she works to reclaim her body, her voice, and her life. If you would like to reach out to the Betrayal Team, email us at betrayalpod@gmail.com. Follow us on Instagram @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    Crime Junkie

    Crime Junkie

    Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.

    Stuff You Should Know

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    On Purpose with Jay Shetty

    On Purpose with Jay Shetty

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Dateline NBC

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

Explore

iHeart

Live Radio

Podcasts

Artist Radio

Exclusives

News

Features

Events

Contests

Photos

Information

About

Advertise

Blog

Brand Guidelines

Contest Guidelines

Subscription Offers

Jobs

Get the App

Automotive

Home

Wearables

© 2026 iHeartMedia, Inc.