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

    1D AGO

    #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 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 and education-based business, why alignment matters more than forcing yourself to stay in a lane that no longer fits, and how community care can be a real business model. They also get gloriously into the weeds on gardening, food systems, and why tomatoes are basically tiny chaotic invaders. This episode is a great one for anyone questioning whether a business pivot is “too much,” “too random,” or “too late.” Dusti’s story is a reminder that sometimes the next right thing has been waiting for you all along. Key Takeaways A pivot can be a return to your real work. Dusti’s move into Hearth & Hollow was not a random detour. It was a deeper expression of her values, skills, and long-term interests.Marketing skills transfer. Dusti shows how relationship-building, education, positioning, and storytelling made it easier to grow a completely different kind of business.Community resilience starts locally. Growing food, sharing plants, and helping neighbors become less dependent on broken systems is meaningful work.You do not have to do business the way everyone else does. Productized services, plant CSAs, education, and local collaborations can create a model that feels both sustainable and values-aligned.Your role in hard times does not have to look like anyone else’s. Dusti makes a strong case for finding your own lane in community care, resistance, and mutual support.Guest & Host Information: Guest, Dusti Arab, Founder of Hearth & HollowCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Dusti: On Instagram: https://www.instagram.com/dustiarab On LinkedIn: https://www.linkedin.com/in/dustiarab On Substack: https://dustiarab.substack.comOn TikTok: https://www.tiktok.com/@dustiarab Learn about Hearth & Hollow: https://www.hearthandhollow.org 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

    44 min

  2. 6D AGO

    #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 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 is essential for sustainability, and what nervous system regulation has to do with making better decisions, plus the usual cozy media recs and a little self-aware chaos. As is tradition. If you’re feeling overwhelmed by the state of the world and trying to keep your business afloat, this episode is both grounding and practical. Key Takeaways Community is resistance. Isolation is the goal of oppressive systems; connection is how people stay resourced, supported, and mobilized.You don’t have to be the hero. Natalia’s reminder lands hard: the “save everything alone” mindset is a burnout pipeline.Collaboration > competition. Sharing knowledge and resources strengthens everyone, and creates a healthier, more sustainable business ecosystem.Visioning is strategic. Dreaming is great, but strategy happens when you turn vision into a plan and take action.Nonprofits are under strain. Limited resources make it even more important to support existing orgs and prioritize work that truly meets urgent needs.Slow down to sustain the fight. Urgency is real, but so is nervous system regulation, because survival mode doesn’t make great decisions.Practical nervous system tips matter. Everything from rest to breathing to literally telling your body “we’re safe” can help shift out of fight-or-flight.Boundaries are business growth. Saying “no” to discounts, protecting calendar time, and limiting meeting overload are real entrepreneurial wins.This episode references our conversation with Natalia Kay-O’Brien, episode #117 on Apple Podcasts, Spotify, and YouTube. 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 The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    34 min
  3. #117: Why Nonprofit Leaders Need Peer Support and Community Now More Than Ever

    MAR 3

    #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 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 building collaborative, relationship-centered spaces where people can be honest, supported, and strategic, without being talked at by the usual conference circuit. If you work in nonprofits, social services, or any community-centered work and you’ve been feeling isolated, overwhelmed, or just plain tired, this will feel like a deep exhale. Note: This episode ends abruptly due to technical issues, but the conversation we did capture is packed with timely insight for the Portland nonprofit space. Key Takeaways:  2025 forced a reset. Losing stable income pushed Natalia to rethink what she wanted her work (and business) to actually be about.Convening is the strategy. Gather (her quarterly happy hour) became proof that people are hungry for connection, and inspired her to build more structured experiences.People need spaces to downshift. Natalia emphasizes regulation, slowing down, and resisting the “urgency treadmill” that burns out helpers first.The Nonprofit Confluence challenges the conference model. Less “expert panels,” more peer wisdom, relationship mapping, asset mapping, and shared visioning.Visioning is survival. Turning away from fear-based consumption and toward imagining what we want to build is part of staying in the work long-term.Tune in to our previous conversations with Natalia Kay-O’Brien, episodes #10 and #82 on Apple Podcasts, Spotify, and YouTube.  Guest & Host Information: Guest, Natalia Kay-O'Brien, Owner of Affinity ProjectsCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Natalia: Visit the Affinity Projects website: https://www.affinityprojects.net Find Natalia on LinkedIn: https://www.linkedin.com/in/nkayobrien For Portland-area folx, join Gather, a happy hour for social good: https://www.affinityprojects.net/gather And Portland-area nonprofits, check out the Nonprofit Confluence, A Solidarity Summit: https://nonprofitconfluence.org The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    40 min

  4. FEB 26

    #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 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 data, and stop running their businesses on autopilot when it comes to security. If you run a business online (and let’s be honest, you do), this episode will help you think more strategically about cybersecurity, digital risk, and why diversifying your marketing platforms isn’t optional. Key Takeaways:  Most tech disasters happen on autopilot. Scams work because you’re distracted, not because you’re unintelligent. Slow down before clicking.Small businesses are prime targets. Hackers often go after smaller companies because the security gaps are easier to exploit.Two-factor authentication is non-negotiable. Add it everywhere, especially for financial accounts, email, and social platforms.You don’t own social media, you’re renting space on it. If your Instagram gets hacked or shut down, what’s your backup plan? Build an email list and own your website.Client access = extra responsibility. Freelancers and consultants must treat client logins and data like gold.This episode references our conversation with Brady Helkenn, episode #115 on Apple Podcasts, Spotify, and YouTube.  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 The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    32 min
  5. #115: What Every Entrepreneur Needs to Know About Cybersecurity with Brady Helkenn

    FEB 25

    #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 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 and give you practical steps to protect your data, your reputation, and your revenue. Key Takeaways: Intentionality is everything. Most tech disasters don’t happen because business owners are “stupid.” They happen because decisions were made on autopilot.Security isn’t about trust. It’s about risk management. Limiting access protects your business from external threats, not from your team.Free tools come with hidden costs. Using personal Gmail for your business or sharing logins instead of assigning permissions can create major vulnerabilities.Budget using depreciation, not panic. If you wait until your laptop crashes to replace it, you’re reacting, not planning.Always verify using a different communication method. In today’s AI-driven scam environment, never confirm suspicious messages through the same channel they came from.Guest & Host Information: Guest, Brady Helkenn, Principal & Jedi Master at BH Tech ConnectionCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Brady: On https://www.linkedin.com/in/bradyhelkennVisit BH Tech Connection: https://bhtechconnection.com Visit Deluxe Sabers: https://www.deluxesabers.comGrab a copy of the book, IT for the 99%: The Small Business Owner’s “IT Hat” Guide: https://www.amazon.com/dp/B0FN8JF43S  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 The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    1h 56m

  6. FEB 19

    #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-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 trying to do “all the things” (and feeling like you’re losing your mind), this episode will help you refocus on what actually matters, plus how to build a business model that fits your real life. Key Takeaways: Entrepreneurship is “reinvention on repeat.” Markets shift, funding changes, tech evolves, and your business has to evolve with it.Nonprofits are in a catch-22: they need stronger storytelling and fundraising right now, but budget cuts and staff reductions make execution harder.Simplify your marketing to what you can actually sustain. Go deeper on fewer platforms instead of spreading thin everywhere.Nonprofit boards need to carry their share, especially in fundraising. If a board approves a deficit budget, the board should be part of the solution.Not everyone needs to scale. A sustainable, values-aligned business is a legit goal, even if startup bros disagree.This episode references our conversation with Liz Ruf, episode #113 on Apple Podcasts, Spotify, and YouTube.  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 The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    35 min
  7. #113: You Don’t Have to Scale to Be Successful with Liz Ruf

    FEB 17

    #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 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. Listen if you’re navigating slow seasons, mission-driven marketing, nonprofit reality checks, or you just need the reminder to trust your gut and stop doing business like it’s 2019. Favorite Takeaways:  Burnout is a real (and common) catalyst to exploring entrepreneurship. Liz left a demanding higher ed role during the pandemic and built her consulting business from there.Entrepreneurship = constant reinvention. You’re adapting to market shifts, client priorities, and funding realities basically every quarter.Nonprofits are in a marketing catch-22 right now. Budget cuts reduce marketing support exactly when storytelling and fundraising need to get stronger.Show up with solutions. The “1-3-1” method: 1 problem, 3 possible solutions, 1 recommendation.Not everyone wants to scale. And that’s valid. Liz calls out the subtle judgment in some startup spaces toward stable, sustainable businesses.Guest & Host Information: Guest, Elizabeth Ruf, Founder & CEO of Elizabeth Ruf Consulting, LLCCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Liz: Website: http://elizabethruf.com LinkedIn: https://www.linkedin.com/in/elizabethruf/ Connect with us: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today Find Ashlan:https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson Find Tory:https://www.instagram.com/imaginemarketingstrategies https://www.linkedin.com/in/victoriaproppe The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    51 min

  8. FEB 12

    #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 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: If you’re building a business and sales feels “icky,” overwhelming, or like something you want to hand off immediately, this episode gives you a more human, practical way to think about sales, and what to focus on first. Favorite takeaways: High achievers often outgrow organizational ceilings. Entrepreneurship can be the “next bar” when you can’t progress further inside a company structure.Entrepreneurship requires a tribe. Community (biz besties, referrals, collaborators) isn’t optional, and it can be a real antidote to the loneliness of building something on your own.Filter advice aggressively. The loudest advice often comes from people who haven’t done the thing. Prioritize voices with context (coaches, peers, trusted operators) and pay attention to who you’re taking advice from.You’re in sales whether you claim it or not. If you own a business, you’re selling–your services, your offer, your value, and your outcomes.Don’t outsource sales too early. If you don’t understand your own sales process end-to-end, hiring someone else to “do sales” can waste time and money, plus it can misalign your messaging.This episode references our conversation with Drew Norton, episode #111 on Apple Podcasts, Spotify, and YouTube.  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  The Course:  The Take the Leap course contains everything you need to know to successfully launch your business now. Sign up today to join the course and get support from Ashlan & Tory who will guide you through your journey as a new entrepreneur. Sign up here: https://www.taketheleap-today.com/the-course  Like our content? Be sure to subscribe and review! Want to keep in touch? Find us on: Youtube Instagram

    33 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
    144
  • Rating
    Explicit
  • Copyright
    © 2026 Take The Leap
  • Show Website
    Take The Leap