She Built a Business by Accident (Then Sold It) with Sarah Jeanneault

She Built a Business by Accident (Then Sold It) with Sarah Jeanneault

Sarah Jeanneault started as a schoolteacher. She did not plan a career in fintech. An unexpected life change pushed her toward a side project. The side project found an audience. The audience became a business. In this episode, Sarah walks through what that transition actually required: listening closely to early followers before the product was fully formed, building community through blogging and early Twitter before either of those was a recognized growth strategy, and staying honest about what was working and what was not in a way most founders avoid. She covers the moment she realized her original customer was not her real customer, what it cost her to make that shift, and how the business changed when she finally built for the right person. She also gets into what happens after an exit, the emotional reality most founders do not talk about until they are on the other side of it. If you are building something from scratch, figuring out who you are actually building for, or trying to understand what comes after the thing you built is gone, this conversation covers all of it honestly. Connect with Sarah: https://www.linkedin.com/in/iam-sarah-potter/ Learn more about our episode sponsor Max Capital Hub: https://maxcapitalhub.com/ #entrepreneurship #startupjourney #fintech #growthmindset

Fired From Corporate. Now He's Disrupting a $6 Billion Industry.

Craig Taylor spent two decades in corporate cybersecurity watching companies train employees the same way, fear, compliance checklists, and the assumption that scaring people into good behavior actually works. It does not. He left to build CyberHoot, a cybersecurity training platform built around positive reinforcement and gamification instead of punishment. In this episode, Craig walks through what that shift actually required: keeping his day job while building, finding a co-founder who filled the gaps he could not, and iterating through multiple versions of the product before landing on what works. He is honest about the moments he almost quit, what psychology taught him about how people actually learn, and why a decade in he is still in the trenches building rather than coasting. If you are building a business in a space dominated by incumbents doing it the old way, this conversation covers what it takes to stay in long enough to find the model that works. Connect with Craig: https://www.linkedin.com/in/craigmtaylor/?skipRedirect=true Learn more about our episode sponsor Max Capital Hub: https://maxcapitalhub.com/ #cybersecurity #startups #entrepreneurship #gamification #leadership

From Recess Monitor to Top-Rated Etsy Seller: Kira Hartley Klinger's Accidental Empire

Kira Hartley Klinger never went to college and never took a business class. She started reselling auction finds out of necessity and turned it into two thriving shops on eBay and Etsy. In this episode, Kira walks through how she scaled from side gigs to a sustainable business by experimenting with products, adapting fast when online marketplaces got more competitive, and developing a selling style that customers actually remembered. She talks about what built her customer loyalty: handwritten notes in every order, real relationships with local communities, and product descriptions that read like stories instead of listings. That same instinct for authentic connection eventually turned her into a self-published author and a sought-after speaker, despite a long-standing fear of public speaking she had to work through first. This episode covers the financial pressure of scaling without outside funding, the decisions that came with growing two shops at once, and what it actually took to put herself in front of an audience for the first time. If you are building something without a traditional background or a clear roadmap, Kira's story is proof that creativity and persistence can build a real business from nothing. Connect with Kira: https://www.linkedin.com/in/kira-hartley-klinger-319a68a5/ Learn more about our episode sponsor, Oceans Talent: https://oceanstalent.com/dave #entrepreneurship #etsy #creativebusiness #smallbusinessjourney

Don't Follow Your Passion: Alyssa Nolte on Why Obsession Wins

In this episode, serial entrepreneur Alyssa Nolte shares her real-life journey from turning down high-paying corporate offers to joining a pre-revenue startup on 100% commission. She breaks down what drove those early bets, how the failures that followed helped her land clients like Salesforce, and why self-belief is the skill founders overlook most. Alyssa talks through the self-doubt that followed an acquisition and what the return to entrepreneurship actually cost her. She also gets into what a real support network looks like, how to tell product obsession from passing interest, and what team culture actually has to do with customer outcomes. Alyssa reflects on growing ology, her company that helps businesses understand why buyers make decisions, and shares what she learned along the way. If you want advice about sales, business model validation, customer relationships, and building resilience as an entrepreneur, this conversation is for you.If you're building something, or trying to, this one's worth your time. Connect with Alyssa: https://www.linkedin.com/in/alyssanolte/ Learn more about our episode sponsor EZDC 3PL: www.ezdc3pl.com #entrepreneurship #podcast #ecommerce #startups

Holding the Checks: Anna Covert on the Day She Took Her Agency Back

In this episode, Dave sits down with Anna Covert, founder of Hawaii’s largest digital marketing agency, bestselling author, and trailblazing entrepreneur. Discover how Anna went from launching lemonade stands and dog-walking businesses as a kid to scaling her own marketing agency, navigating challenges, business partnerships, and industry shifts along the way. She shares honest insights on surviving the ups and downs of running an agency, handling client turnover, evolving with digital trends, and the reality behind taking your business solo. Anna explains her experience growing during economic downturns, innovating in solar and tech, and the importance of being hands-on—whether it’s managing a marketing campaign or writing bestselling business books. Perfect for entrepreneurs seeking new ways to adapt, build value, and connect with their audience, don’t miss this candid journey through the highs and lows of real-world entrepreneurship. Connect with Anna: https://www.linkedin.com/in/anna-covert/ Learn more about our episode sponsor: https://oceanstalent.com/dave #entrepreneurship #digitalmarketing #podcast #personalbranding #womeninbusiness