Take The Leap

Victoria Proppe & Ashlan Glazier-Anderson
  • 5.0 (4)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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!" 

  1. 10H AGO

    #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 unpack why so many organizations struggle with transitions, why healthy exits are still surprisingly rare, and how businesses can create better systems for both the people leaving and the people staying behind. The conversation also explores entrepreneurship, burnout, rest, and the importance of building sustainable systems both at work and at home. If you’ve ever left a job awkwardly, struggled with boundaries around time off, or wondered why workplace transitions feel so emotionally loaded, this episode will absolutely resonate. Key Takeaways Most workplaces are not prepared for healthy transitions, even though employee turnover is inevitable.Two weeks’ notice is often not enough for meaningful knowledge transfer or relationship closure.Organizations should normalize conversations about departures, succession planning, and sabbaticals.Asking about offboarding processes during interviews can reveal a lot about workplace culture.Knowledge transfer is more about communication and support than creating the “perfect binder.”Time off should not require burnout-level preparation just to step away for a few days.Entrepreneurs and organizations alike need systems that support rest and recovery.Community and relationships require intentional maintenance, especially during busy seasons.This episode references our conversation with Naomi Hattaway, episode #129 on Apple Podcasts, Spotify, and YouTube. And listen to our first conversation with Naomi episode #35. Host information: Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies Connect: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today With Ashlan:https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson With Tory:https://www.instagram.com/imaginemarketingstrategies https://www.linkedin.com/in/victoriaproppe Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    31 min
  2. #129: The Realities of Workplace Transitions, Succession Planning, and Normalizing People Leaving

    2D AGO

    #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, leadership transitions, mergers, and meaningful goodbyes, Naomi brings a deeply human lens to what can often feel like operational or uncomfortable topics. This episode is especially valuable for nonprofit leaders, founders, and business owners who know that people leaving is inevitable, but want to handle those transitions with more care, clarity, and humanity. Naomi reminds us that succession planning is not a sign of failure or departure. It is a way to protect the work, honor relationships, and build organizations that can keep moving forward. Key Takeaways Succession planning is not just for CEOs. Every role holds knowledge, relationships, and context that matter. Planning for people to leave helps protect the mission and the team.Two weeks’ notice is rarely enough for meaningful transition. Naomi challenges the default exit timeline and invites leaders to think more intentionally about what people, relationships, and projects need before someone leaves.Good departures are part of healthy workplace culture. How an organization handles exits says a lot about how it values people and not just their productivity.Sabbaticals require reentry planning, not just departure planning. When someone steps away, the organization changes, and so does the person returning.Nonprofits need to normalize mergers, sunsets, and strategic endings. Closing or combining organizations does not have to mean failure. It can be a thoughtful way to protect impact.Leaders should ask better questions before joining an organization. One powerful interview question Naomi recommends: “What is your process when someone leaves?”Knowledge transfer does not have to mean creating the perfect binder. Sometimes the most helpful thing is documenting why decisions were made, not just how tasks are completed.Funders have a role to play in protecting organizational continuity. Foundations can support succession planning as part of protecting their investment in nonprofit missions.Leaving well starts with communication. Whether at work, in business, or around the kitchen table, we can all help normalize conversations about change, departure, and transition.Guest & Host Information: Guest, Naomi Hattaway, Founder of 8th & HomeCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Naomi: Take the Quiz to find your Transition Readiness Archetype: https://www.naomihattaway.com/assessment On Instagram: @naomihattaway: https://instagram.com/naomihattawayOn LinkedIn: https://linkedin.com/in/naomihattaway Visit Naomi’s website: https://www.naomihattaway.com/Read Naomi’s book on Leaving Well: https://www.naomihattaway.com/book Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    58 min

  3. MAY 7

    #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 business around the life you want instead of letting your business run the show. This episode is a reminder that big dreams rarely happen by accident. Whether your goal is full-time travel, more time with your family, better health, or deeper community, the life you want starts with intentional choices, aligned business models, and the courage to stop treating “someday” like a strategy. Key Takeaways Your business should support your life, not control it. Entrepreneurship gives you flexibility, but only if you intentionally build for it.Your community does not have to be local; connection can be global, online, and built across seasons of life.You are not starting over when you start a business after a career; your expertise still counts.Pricing should reflect your experience, not just how long you have been an entrepreneur.This episode references our conversation with Eunice Brownlee, episode #127 on Apple Podcasts, Spotify, and YouTube. You can listen to our first conversation with Eunice, episode #74. Host information: Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today With Ashlan:https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson With Tory:https://www.instagram.com/imaginemarketingstrategies https://www.linkedin.com/in/victoriaproppe Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    33 min
  4. #127: What 4 Months of Solo Travel Taught Eunice About Business and Life

    MAY 5

    #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 traveling solo across Europe and Asia, all while running a fully remote business. From house sitting on a farm in France to navigating trains, time zones, and mindset shifts, Eunice shares what it really takes to turn a long-held dream into reality. This conversation goes far beyond travel. We dive into intentional life design, building a business that supports your freedom, and the difference between dreaming about a life you want and actually taking action to create it. If you’ve ever wondered what it looks like to truly align your work, lifestyle, and values, this episode will expand what you believe is possible. Key Takeaways: The difference between a dream and reality is action. Big, audacious goals only become real when you start designing your life around them. Eunice didn’t “luck into” four months of travel. She intentionally built a business and lifestyle that made it possible.You don’t need the full plan, just the next step. Progress came from taking action, gathering data, and adjusting along the way. Your business should support your life, not the other way around. Eunice’s ability to travel came from creating a flexible, asynchronous business model that wasn’t dependent on location or rigid schedules.Freedom requires intentional trade-offs. Traveling long-term meant packing strategically, limiting purchases, navigating uncertainty, and making real-time financial decisions, not just living in a highlight reel.Global perspective will challenge your assumptions. Experiencing other cultures, especially around cost of living, food systems, and community, can completely shift how you view “normal” in the U.S.Community doesn’t have to be local. Building a global network allowed Eunice to travel more meaningfully and sustainably, blending connection, work, and exploration.Guest & Host Information: Guest, Eunice Brownlee, Founder of thirty9collectiveCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Eunice: On Instagram @eunicebrownlee: https://instagram.com/eunicebrownleeOn LinkedIn: https://linkedin.com/in/eunicebrownleeOn YouTube: https://www.youtube.com/@eunicebrownleeVisit Eunice’s website: https://eunicebrownlee.com/ Connect with us: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    55 min

  5. APR 16 ·  BONUS

    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 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 business but weren’t sure where to begin, this is your chance to dive in without barriers. Ashlan also shares what’s coming next, including deeper-dive workshops and community-focused opportunities later this year. Tune in for a quick update, a meaningful pivot, and a reminder that sometimes the best way to support your audience is to meet them exactly where they are. Host information: Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with us: Subscribe to our YouTube channel:https://www.youtube.com/@TaketheLeap-Today Follow us on Instagram @taketheleap_today:https://www.instagram.com/taketheleap_today Find Ashlan on Instagram & LinkedIn: https://www.instagram.com/ashbeanpdxmktg/https://www.linkedin.com/in/ashlan-glazier-anderson/ Find Tory on Instagram & LinkedIn https://www.instagram.com/imaginemarketingstrategies/ https://www.linkedin.com/in/victoriaproppe/ Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    3 min

  6. APR 7 ·  BONUS

    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 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/@TaketheLeap-Today  And finally, if you feel up to it…. Send us a DM on Instagram: https://www.instagram.com/taketheleap_today Or email us at aloha@taketheleap-today.com We’ve interviewed 20 amazing guests this season. Here are their names & episode numbers, please give them a listen:  #087 - Mary Williams, Founder of Sasquatch Media Grounds#089 - Stephen Brent May & Hami Arrington, Founders of One Foot Over in Houston, Texas#091 - Zhou Fang, Founder of the Intersectional Group#093 - Sean Murphy, Founder of Lore Works Creative Studio#095 - Aneisha Velasquez, Founder of Yellow Sky Business Services#097 - Eliana Mendez, Founder of Human Centric Media#099 - Mady Spry, Founder of High Topp Marketing#101 - Nedra Rezinas, Marketing Coach #103 - Mark Mohammadpour, Keynote Speaker at Chasing the Sun#105 - Money Coach at Gemini Financial Wellness and Moxie and Might Money Coaching#107 - Fatima Jawaid Marty, Nonprofit Consultant at FJM Consulting#109 - Alayna Weimer, HR and business consultant with Ignite Positive Changes #111 - Drew Norton, the Everyday Sales Leader#113 - Liz Ruf, Founder, Elizabeth Ruf Consulting#115 - Brady Helkenn, Principal at BH Tech Connection#117 - Natalia Kay-O'Brien, Founder of Affinity Projects and the quarterly networking happy hour, Gather in Portland, Oregon#119 - Dusti Arab, Founder of Hearth & Hollow#121 - Megan Eckman, Creator of PDX Spellbound and Founder of Fat Cap Design#123 - Haley Cooper, The Savvy Fundraiser#125 - Nick Footer, Cultivator of Happiness and CEO of Intuitive DigitalBy the end of this season, we’ll have published 153 episodes of the Take the Leap Podcast. And we have big plans for our fourth season. Thank you again for being a listener, and stay tuned for episode #127, publishing next Tuesday, April 14, with returning guest, Eunice Brownlee.  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    5 min

  7. APR 2

    #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 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 businesses in ways that are sustainable, flexible, and aligned with reality, not just theory. Plus, we unpack why AI isn’t replacing marketers anytime soon, but is changing how we think about strategy, content, and trust. If you’ve ever felt pressure to grow faster, hire sooner, or chase every new marketing trend, this episode will help you slow down, think smarter, and build a business that actually supports you long-term. Key Takeaways Don’t scale your business before the revenue is real. Hiring ahead of confirmed income can quickly put you in a position where you’re responsible for paying others before paying yourself, and that’s not sustainable.Contractors can be a smarter path than employees (especially early on). Building a flexible team allows you to grow without taking on unnecessary financial risk tied to payroll.AI is changing marketing, but it’s not replacing marketers. Tools can support efficiency, but strategy, messaging, and emotional connection still require human insight.Over-reliance on AI can weaken your brand voice. If everything sounds the same, you lose the very thing that makes your marketing effective: differentiation.Automation should be used intentionally, not blindly. Just because something can be automated doesn’t mean it should be, especially when money, trust, or brand reputation is involved.This episode references our conversation with Nick Footer, episode #125 on Apple Podcasts, Spotify, and YouTube. You can learn more about Nick and Intuitive Digital online: https://intuitivedigital.com  Host information: Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today With Ashlan:https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson With Tory:https://www.instagram.com/imaginemarketingstrategies https://www.linkedin.com/in/victoriaproppe Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    27 min
  8. #125: Building a Values-Driven Agency with Nick Footer

    MAR 31

    #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 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 marketing nerd trying to make sense of AI, automation, and today’s shifting economy–this episode is packed with practical wisdom and real-world perspective. Key Takeaways:  Don’t scale before the revenue is real. Hiring and expanding before contracts are signed can create years of financial stress. Your growth should follow confirmed demand.AI isn’t replacing marketing strategy–it’s changing it. Businesses now need to optimize for SEO, AEO (AI Engine Optimization), and GEO (Generative Engine Optimization).Automation isn’t always your friend. Blindly trusting automated ad campaigns can lead to inflated “conversion” data that doesn’t translate to real revenue.Purpose still matters in tough markets. Being B Corp certified and values-driven isn’t just branding–it shapes how you build culture, serve clients, and make decisions.Marketing budgets are tightening–but strategy matters more than ever. The businesses that survive downturns are the ones that get focused, track attribution, and adapt quickly.Guest & Host Information: Guest, Nick Footer, CEO of Intuitive DigitalCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Nick: Website: https://intuitivedigital.com/ LinkedIn: https://www.linkedin.com/in/nickfooter/ Connect with us: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today Find Ashlan on Instagram & LinkedIn: https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson Find Tory on Instagram & LinkedIn https://www.instagram.com/imaginemarketingstrategies https://www.linkedin.com/in/victoriaproppe Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    55 min
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5
out of 5
4 Ratings

About

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!" 

Information

  • Creator
    Victoria Proppe & Ashlan Glazier-Anderson
  • Years Active
    2024 - 2026
  • Episodes
    157
  • Rating
    Explicit
  • Copyright
    © 2026 Take The Leap
  • Show Website
    Take The Leap