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PODCAST

Take The Leap

Victoria Proppe & Ashlan Glazier-Anderson

Take the Leap is the podcast where we get real about the rollercoaster that is entrepreneurship and life.Sure, some folks make running a business look like a walk in the park, but let"s be honest – it"s more like a wild ride through a theme park with unexpected twists and turns!Join us your co-hosts, Victoria & Ashlan, as we spill the beans on our own real-life experiences and shine a spotlight on some amazing guests. From the highs of success stories to the lows of epic failures, and hey, we"ll

business entrepreneurship

All Episodes

2:34

Extended Break - Back with New Episodes on May 5

Take The Leap ·

2026/04/16

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 is officially becoming free and accessible on YouTube. If you’ve been thinking about starting a b...

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4:35

We're on Spring Break

Take The Leap ·

2026/04/07

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 our YouTube and leave us comments on your favorite episodes here: https://www.youtube.com/@Ta...

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27:12

#126: Before You Scale - What Every Business Owner...

Take The Leap ·

2026/04/02

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. We share our own experiences navigating growth, hiring (and un-hiring), and structuring our bus...

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55:12

#125: Building a Values-Driven Agency with Nick Footer

Take The Leap ·

2026/03/31

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 sustain a values-based business. If you’re a service-based entrepreneur, nonprofit leader, or marketi...

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25:06

#124: Burnout is a Culture Problem, Not a Personal...

Take The Leap ·

2026/03/26

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 strategies and healthier team cultures. We’re bringing in our own experiences from working inside nonprofi...

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44:05

#123: Boundaries, Burnout, and Better Nonprofit...

Take The Leap ·

2026/03/24

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-centered. From launching The Savvy Fundraiser during maternity leave to writing a book, hosting a...

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29:41

#122: You Don’t Need More Followers, You Need Better...

Take The Leap ·

2026/03/19

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 show why audience quality matters more than audience size, and how focusing on the wrong metri...

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57:27

#121: The Audience-Building Strategy Most...

Take The Leap ·

2026/03/17

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 a fan base before you launch is the difference between crickets… and a stadium full of people re...

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31:25

#120: When a Business Pivot is Actually a Homecoming

Take The Leap ·

2026/03/12

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 matches her values. They also unpack why community is more than a buzzword right now, how local action ...

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43:54

#119: The Pivot that Finally Felt Like Alignment with...

Take The Leap ·

2026/03/10

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 conversation explores what it looks like to pivot from service-based marketing work into a product ...

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33:53

#118: Nonprofits, Burnout, and the Case for...

Take The Leap ·

2026/03/05

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 business owners). They also dig into how “visioning” can be strategic (not fluffy), why slowing down...

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40:22

#117: Why Nonprofit Leaders Need Peer Support and...

Take The Leap ·

2026/03/03

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 and social services professionals. This episode explores the shift from “doing it all alone” to b...

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31:36

#116: How to Protect Your Business from Email Scams...

Take The Leap ·

2026/02/26

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 reflect on the practical steps entrepreneurs can take right now to reduce risk, protect client d...

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115:56

#115: What Every Entrepreneur Needs to Know About...

Take The Leap ·

2026/02/25

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 a small team) and think “that won’t happen to me,” this conversation will challenge that mindset ...

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35:18

#114: How to Simplify Marketing When You’re...

Take The Leap ·

2026/02/19

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 why not every entrepreneur needs to scale. If you’re a small business owner or nonprofit leader try...

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51:09

#113: You Don’t Have to Scale to Be Successful with...

Take The Leap ·

2026/02/17

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 funding cuts in the nonprofit world, and why community isn’t optional when you work for yourself....

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32:40

#112 - Sales for Small Business Owners: A Better Way...

Take The Leap ·

2026/02/12

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, and how to build a support network so entrepreneurship doesn’t feel like an island. Why listen: ...

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38:53

#111: Sales is Life: How to Lead (and Sell) Without...

Take The Leap ·

2026/02/10

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 selling, build a sales process that feels ethical, or figure out when it’s time to leap again. F...

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35:50

#110: Why Support Systems Matter More Than You Think

Take The Leap ·

2026/02/05

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’re an entrepreneur trying to stay sane while building something sustainable. This episode gives yo...

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38:47

#109: Ditching the One-Size-Fits-All Business Advice...

Take The Leap ·

2026/02/03

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 owner or nonprofit leader who feels overwhelmed by “HR stuff,” wants to build a healthier workpla...

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160 results

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