Take The Leap
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 even throw in some cringe-worthy, laugh-out-loud embarrassing moments for good measure!
So buckle up and tune in every week for a dose of raw, unfiltered truth about what it's really like to chase your dreams and build a business. Whether you're a seasoned entrepreneur or just dipping your toes into the startup world, we've got something for everyone. Even if it's just to make you think, "I'm so glad I didn't do what they did!"
Episodes
153 episodes
Extended Break - Back with New Episodes on May 5
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...
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2:34
We're on Spring Break
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 li...
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4:35
#126: Before You Scale - What Every Business Owner Needs to Know
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 ...
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Season 3
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Episode 40
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27:12
#125: Building a Values-Driven Agency with Nick Footer
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 growi...
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Season 3
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Episode 39
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55:12
#124: Burnout is a Culture Problem, Not a Personal Failure
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 big...
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Season 3
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Episode 38
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25:06
#123: Boundaries, Burnout, and Better Nonprofit Leadership
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 experienc...
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Season 3
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Episode 37
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44:05
#122: You Don’t Need More Followers, You Need Better Ones
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 l...
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Season 3
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Episode 36
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29:41
#121: The Audience-Building Strategy Most Entrepreneurs Skip
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...
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Season 3
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Episode 35
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57:27
#120: When a Business Pivot is Actually a Homecoming
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 ...
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Season 3
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Episode 34
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31:25
#119: The Pivot that Finally Felt Like Alignment with Dusti Arab
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 smal...
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Season 3
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Episode 33
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43:54
#118: Nonprofits, Burnout, and the Case for Supporting What Already Exists
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 effec...
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Season 3
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Episode 32
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33:53
#117: Why Nonprofit Leaders Need Peer Support and Community Now More Than Ever
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 ...
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Season 3
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Episode 31
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40:22
#116: How to Protect Your Business from Email Scams and AI Spoofing
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...
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Season 3
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Episode 30
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31:36
#115: What Every Entrepreneur Needs to Know About Cybersecurity with Brady Helkenn
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 fo...
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Season 3
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Episode 29
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1:55:56
#114: How to Simplify Marketing When You’re Under-Resourced
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...
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Season 3
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Episode 28
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35:18
#113: You Don’t Have to Scale to Be Successful with Liz Ruf
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 unh...
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Season 3
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Episode 27
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51:09
#112 - Sales for Small Business Owners: A Better Way to Think About Selling
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 unlo...
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Season 3
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Episode 26
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32:40
#111: Sales is Life: How to Lead (and Sell) Without Feeling Sleazy
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 ge...
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Season 3
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Episode 25
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38:53
#110: Why Support Systems Matter More Than You Think
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 tha...
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Season 3
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Episode 24
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35:50
#109: Ditching the One-Size-Fits-All Business Advice with Alayna Weimer
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 re...
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Season 3
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Episode 23
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38:47
#108: Conversations About Nonprofit Sustainability and Burnout
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 ...
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Season 3
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Episode 22
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24:47
#107: From Burnout to Boundaries: Building a Consulting Practice for the Long Haul
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 c...
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Season 3
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Episode 21
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1:00:18
#106: Business Emergency Funds – The Money Move Entrepreneurs are Guilty of Avoiding
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. Th...
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Season 3
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Episode 20
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22:53
#105: Your Money Mindset is an Important Business Strategy with Julie Stair
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 m...
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Season 3
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Episode 19
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32:56
#104: Streamline + Gather, Our Words of the Year + How We’re Approaching 2026
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 ...
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Season 3
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Episode 18
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19:30