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
163 episodes
#136: Remember You Don’t Need to Work With Everyone, Why Aligned Clients Matter
In this solo recap episode, Ashlan and Tory reflect on their conversation with Marina Martinez-Bateman and unpack the realities of consulting, nonprofit work, professionalism, and building a business rooted in alignment rather than performative...
#135: Real Talk on Capitalism, Consulting, and Client Work
In this unfiltered and wide-ranging conversation, Marina Martinez-Bateman returns to share what it actually looked like to survive one of the most volatile years many nonprofit professionals have ever experienced. From losing clients week after...
#134: You Don’t Owe the Internet Your Presence Everywhere
In this solo recap episode, Ashlan and Tory reflect on their conversation with writer and writing coach Sam Pollack and unpack the pressure entrepreneurs feel to constantly create content, stay visible online, and “play the algorithm game.”...
#133: The Anti-Algorithm Strategy: SEO, Email, and Real Connection
In this candid and refreshingly honest conversation, we sit down with returning guest Samantha (Sam) Pollack to talk about what it really looks like to navigate a business pivot in today’s ever-changing marketing landscape. From walking away fr...
#132: Business, Politics, and Community Impact
In this recap episode, Ashlan and Tory reflect on their conversation with Michael Jonas and dive deeper into collaboration, community-building, networking, and the scarcity mindset that often shows up in entrepreneurship.They explore why...
#131: Stop Waiting for Better Systems and Start Building Them Instead
In this powerful and wide-ranging conversation, we welcome back Michael Jonas for a candid update on his work, from launching innovative community-building tools like the Narwhal Pod to diving into big, uncomfortable questions through his new p...
#130: Building Better Workplace Transitions
In this recap episode, Ashlan and Victoria reflect on their powerful conversation with Naomi Hattaway about leaving well, workplace culture, sabbaticals, succession planning, and the reality that no one stays in a role forever.They unpac...
#129: The Realities of Workplace Transitions, Succession Planning, and Normalizing People Leaving
In this conversation, Naomi Hattaway returns to talk about what it really means to design your work, your leadership, and your life with intention. From building a home meant for aging in place to preparing organizations for sabbaticals, leader...
#128: Building a Business that Fits Your Life Goals, Not the Other Way Around
In this solo recap episode, Ashlan and Tory reflect on their conversation with Eunice and the way she intentionally redesigned her business to support a more flexible, travel-centered life. They explore what it really means to build your busine...
#127: What 4 Months of Solo Travel Taught Eunice About Business and Life
What happens when you stop waiting for “someday” and actually design your life around the things you say you want?In this episode, we sit down with returning guest Eunice Brownlee to talk about her bold decision to spend four months trav...
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...
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...
#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 ...
#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...
#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...
#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...
#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...
#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...
#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 ...
#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...
#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...
#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 ...
#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...
#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...
#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...