Take The Leap

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...

Returning guest Mark Mohammadpour shares how Chasing the Sun has evolved from coaching to a keynote-driven business and what he’s seeing in workplace wellbeing as companies navigate hybrid work, AI acceleration, and rising employee isolation. Tory and Ashlan dig into what makes conference culture actually work (hint: it’s not another panel that “could’ve been an email”), and Mark offers a simple b...

In this debrief episode, Ashlan and Tory reflect on their recent conversation with Nedra and pull out the real-life business lessons that stuck–especially around pivoting, boundaries, and relationship-based networking. They talk candidly about end-of-year chaos, the pressure to do “all the things,” and what it looks like to build a business that actually fits your energy, life stage, and brain wir...

In this episode, Tory and Ashlan welcome back Nedra Rezinas, a marketing strategist, coach, and educator with 20+ years of business experience. Nedra shares how her work has evolved beyond marketing into deeper coaching–helping entrepreneurs (especially introverted, highly sensitive, empathy-driven business owners) build confidence, make decisions, and find sustainable ways to grow. Tune in if you...

Hey listeners, we just wanted to pop in and wish you a happy holiday week.  We’re taking a much needed break from recording and publishing content this week to spend time with our families.  We invite you to listen to our past episodes, if you haven’t listened to Seasons 1 & 2, in 2026 we’ll have a number of guests from those seasons returning to be on the mic with us again.  We’re wishing you...

Welcome to the 14th episode of Take the Leap's third season. In today’s episode, “Stop Trying to Beat the Algorithm and Start Building a Strategy,” co-hosts Ashlan and Victoria debrief their conversation with Mady Spry, founder of High Topp Marketing. We dig deeper into what makes social media marketing actually work, especially for bars and restaurants, and why “posting just to post” or “try...