Take The Leap

In this short solo update, Ashlan shares a quick behind-the-scenes moment from the Take the Leap team, along with an exciting announcement you won’t want to miss. While Tory takes some much-needed time to recover (sending all the good vibes her way), Ashlan walks listeners through a big shift in how Take the Leap is showing up for aspiring entrepreneurs. The biggest news? The Take the Leap course...

Thank you for tuning in to the Take the Leap podcast. Ashlan and Tory are taking a much needed spring break this week. But we have some asks from you. If you enjoy our podcast, please write us a review on Apple or Spotify. Here are the links:  https://podcasts.apple.com/us/podcast/take-the-leap/id1735641469 https://open.spotify.com/show/4eMBeH8Ks4HGOKahnMD53U?si=72550a3612ee4df4 Or you can visit o...

In this solo episode, we’re breaking down our conversation with Nick Footer, founder of Intuitive Digital, and diving deeper into the real-world lessons behind building and scaling a marketing agency. From the risks of scaling too early to the evolving role of AI in marketing, this conversation highlights what actually works, and what can quietly derail your business if you’re not paying attention...

Nick Footer, CEO of Intuitive Digital and self-proclaimed “Cultivator of Happiness,” joins us to talk about building a purpose-driven marketing agency, navigating economic uncertainty, and why AI isn’t killing SEO, it’s reshaping it. From growing up in a family of entrepreneurs to leading a B Corp-certified agency, Nick shares honest insights about risk, scaling, and what it actually takes to sust...

After our conversation with Haley Cooper, we couldn’t stop thinking about one big question: what does it actually take to build organizations that support both the mission and the people behind it? In this episode, we’re unpacking the biggest themes from our conversation with Haley Cooper, from nonprofit burnout and reactive leadership to the real work of building sustainable fundraising strategie...

What happens when motherhood, burnout, and a deep belief in people-first leadership collide? You build a business that challenges the way nonprofits work from the inside out. In this episode, Haley Cooper shares how she took her experience in fundraising, leadership, and nonprofit strategy and turned it into a business focused on helping organizations become more connected, sustainable, and human-...

Think you need more followers to grow your business? Not so fast. In this recap episode, we break down our conversation with Megan Eckman and dig into one of the biggest misconceptions in entrepreneurship: that a bigger audience automatically leads to more sales.  Spoiler alert…it doesn’t. We’re sharing real examples (including clients with tens of thousands of followers and zero engagement) to sh...

If you’ve ever thought, “I just need better marketing”… this episode might lovingly call you out. We’re joined by returning guest Megan Eckman, founder of Fat Cap and creator of PDX Spellbound, to talk about the step most entrepreneurs skip and why it’s costing them time, money, and momentum. Spoiler: it’s not your logo, your website, or your ads. It’s your audience. Megan breaks down why building...

In this response episode, Ashlan and Tory debrief their conversation with returning guest Dusti Arab and reflect on what it really looks like to pivot a business into deeper alignment. They talk about Dusti’s evolution from marketing work into community-centered food growing through Hearth & Hollow, and how that shift was not a random reinvention so much as stepping fully into work that matche...

In this episode, Ashlan and Tory sit down with returning guest Dusti Arab at Sasquatch Media Grounds to talk about what has changed since her last appearance and wow, a lot has changed. Dusti shares how Hearth & Hollow has grown from a small, values-led idea into a business centered on local resiliency, community food access, plant starts, and helping people grow more of their own food. The co...

In this response episode, Ashlan and Victoria debrief their conversation with returning guest Natalia Kay-O’Brien and unpack why community building is a survival strategy right now and not just a “nice-to-have.” They reflect on the ripple effects of 2025 on nonprofit and consulting work, the myth of needing a hero to save everything, and why collaboration beats competition (especially for solo bus...

Natalia Kay-O’Brien returns for her third appearance on Take the Leap to talk about what it really looks like to keep building community while everything feels like it’s on fire (politically, socially, financially… pick a lane). She shares how a tough year, including losing a major retainer, pushed her into deeper R&D and ultimately into creating new, more intentional convenings for nonprofit...

In this recap episode, we unpack our conversation with cybersecurity expert Brady Helkenn and the sobering reality that small businesses are not too small to be targeted. From spoofed emails and AI-generated voice scams to password overload and platform dependency, this conversation is your reminder that tech disasters rarely happen because you’re “bad at tech,” they happen because you’re busy. We...

Brady Helken returns to the podcast to talk about his new book IT for the 99% and why small business owners need to stop treating tech like an afterthought. From cybersecurity myths and tool sprawl to disaster recovery planning and budgeting for inevitable upgrades, this episode is a masterclass in running a smarter, safer business. Why listen: If you run a small business (especially solo or with...

In this recap episode, Ashlan and Tory debrief their conversation with Liz Ruf of Elizabeth Ruff Consulting and pull out the big entrepreneurship lessons: building a business for freedom, staying adaptable through market shifts, and why mission-driven work is getting hit hard by funding realities. They also talk nonprofit board accountability, simplifying marketing when resources are tight, and wh...

Ashlan and Victoria sit down with Elizabeth (Liz) Ruf, a strategic marketing advisor who works with higher ed, EdTech, and mission-driven organizations, to talk about taking the leap into entrepreneurship during the COVID chaos era (a truly unhinged time to start a business, 10/10). Liz shares how burnout pushed her to quit without a safety net, what it’s like to run a consulting business through...

In this solo recap episode, Ashlan and Tory unpack key lessons from their conversation with Drew Norton, the Everyday Sales Leader, including why ambitious professionals often hit ceilings inside organizations, and how entrepreneurship can unlock a new level of growth. They also dig into why sales is part of every business (even if you hate the label), why outsourcing sales too early can backfire,...

Ashlan and Tory chat with Drew Norton, the Everyday Sales Leader, about taking big career leaps, leaving “secure” income behind, and building sales teams that don’t feel gross. Drew shares how he went from door-to-door sales to leading teams generating ~$20 million/year in revenue, then took another leap into coaching and consulting so he could help others grow. Listen if you want to get better at...

In this recap episode, Ashlan and Tory debrief their conversation with HR and business consultant Alayna Weimer and pull out the biggest lessons entrepreneurs can apply right now–especially around agency, leadership, and building a business that supports real life. You’ll also hear a candid check-in on systems, boundaries, and the weekly “wins/do-betters” that keep momentum going. Tune in if you’r...

In this episode, Ashlan and Tory sit down with Alayna Weimer, HR and business consultant and co-owner of the Herringbone Bookstore in Redmond, Oregon. Alayna shares her journey from a long corporate HR career into entrepreneurship, what it’s really like to be married to another entrepreneur, and why human-centered leadership matters more than ever. This is a must-listen if you’re a small business...

In this solo recap episode, Ashlan and Tory reflect on their powerful conversation with Fatima (Episode 21) and dig deeper into what it really means to build sustainable, long-term capacity–especially in nonprofit and mission-driven work. They unpack common pitfalls around grant funding, program design, burnout, and discovery calls, while sharing candid reflections from their own businesses. Liste...

Returning guest Fatima Jawaid Marty, founder of FJM Consulting, joins Ashlan and Tory to talk about what’s shifted over the past year, both personally, professionally, and in the broader nonprofit/policy landscape. They get real about how the current political climate and funding uncertainty are affecting mission-driven work, then pivot into practical ways consultants can prevent burnout, set boun...

In this recap episode, Tory and Ashlan debrief their conversation with money coach Julie Stair and pull out the real-world lessons that hit home–especially around emergency savings, money mindset, and avoiding debt while building a business. They also share a few practical “we’ve been there” examples (hello, dead laptop) and talk through how entrepreneurs can reduce money stress without pretending...

In this episode, Ashlan and Tory talk with Julie Stair, a money coach and single mom who helps professionals, especially single mothers, take control of their finances with clarity, confidence, and a little sparkle. Julie shares her real-life money journey: getting out of debt, getting back into debt, navigating divorce, and rebuilding financially and then turning all of that into a coaching busin...

In this episode, Ashlan and Victoria debrief their conversation with Mark Mohammadpour and pull out the big themes that apply to basically every entrepreneur: your business will evolve, your skills stack matters, and burnout culture is not the vibe. They also share their Word of the Year for 2026, plus what they’re reading/watching right now. Listen if you’re heading into 2026 wanting a reset, a c...