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. 14H AGO

    #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
  2. #111: Sales is Life: How to Lead (and Sell) Without Feeling Sleazy

    2D AGO

    #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 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. Favorite takeaways: Ceilings are real, especially inside organizations. Entrepreneurs often leap when they can’t progress or create impact where they are.Find your “tribe.” Entrepreneurship gets lonely; community (masterminds, networking, mentors, even “buy someone lunch”) speeds up progress.The worst advice usually comes from people who haven’t done the thing. Filter your input accordingly.Sales isn’t about pressuring people to make a choice. Great sales help people clarify what happens if they don’t change.Business owners are salespeople… even if they hate the label. If you have a business, you sell something.Don’t outsource sales too early. Early-stage founders often need to own sales longer than they want to.Guest & Host Information: Guest, Drew Norton, The Everyday Sales LeaderCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Drew: Website: https://theeverydaysalesleader.com/ Instagram: https://www.instagram.com/theeverydaysalesleader/ LinkedIn: https://www.linkedin.com/in/theeverydaysalesleader/ YouTube: https://www.youtube.com/@theeverydaysalesleader TikTok: https://www.tiktok.com/@theeverydaysalesleader Facebook: https://www.facebook.com/theeverydaysalesleaderConnect with us: On YouTube: https://www.youtube.com/@TaketheLeap-Today On Instagram: https://www.instagram.com/taketheleap_today 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

    39 min

  3. FEB 5

    #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 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 you practical mindset shifts and simple operational takeaways you can actually use. Our Favorite Takeaways:  Agency is the point: You can’t control the economy (or the chaos), but you can control how you respond. And entrepreneurship gives you more say in your day-to-day than most traditional roles.Care builds credibility: “People don’t care how much you know until they know how much you care” isn’t a cute quote. It’s a business strategy for trust, retention, and referrals.The best system is the one you’ll use: Fancy tools don’t matter if they require too much brainpower. Keep it simple, reduce friction, and design your workflow around how you actually operate.Email organization ≠ task completion: Setting up an inbox framework is step one; building the habit of regularly clearing action items (and tracking “waiting on”) is what makes it work.Progress over perfection: Time blocking, grouping tasks, and building routines are skills. You should expect iteration, not instant mastery.This episode references our conversation with Alayna Weimer, episode #109 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

    36 min
  4. #109: Ditching the One-Size-Fits-All Business Advice with Alayna Weimer

    FEB 3

    #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 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 workplace culture, or needs reassurance that you don’t have to follow someone else’s formula to succeed. Some of our favorite takeaways from this episode include:  Entrepreneurship offers control, not chaos. While you can’t control the market, owning your business gives you flexibility and agency, especially during economic shifts or life changes.Fail fast (and with grace). Alayna emphasizes learning quickly, letting go of perfectionism, and not dwelling on mistakes as a key to long-term success.People don’t care how much you know until they know how much you care. This principle applies to leadership, HR, client relationships, and community work.Many business problems aren’t what they seem. What looks like a bookkeeping or systems issue is often a leadership, capacity, or people-alignment challenge underneath.The best systems are the ones you’ll actually use. Whether it’s HR processes or productivity tools, simplicity and consistency matter more than fancy platforms.Guest & Host Information: Guest, Alayna Weimer, CEO & Founder of Ignite Positive ChangesCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Alayna: Website: https://www.ignitepositivechanges.comLinkedIn: https://www.linkedin.com/in/alayna-marie-discover-your-successInstagram: https://www.instagram.com/ignitepositivechangesllcFacebook: https://www.facebook.com/ignitepositivechangesllc Connect with us: YouTube: https://www.youtube.com/@TaketheLeap-Today 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

    39 min

  5. JAN 29

    #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 unpack common pitfalls around grant funding, program design, burnout, and discovery calls, while sharing candid reflections from their own businesses. Listen if you’re a nonprofit leader, consultant, or solopreneur who wants to build something that actually lasts (without running yourself into the ground or chasing shiny funding at all costs). Key Takeaways Don’t build programs just to chase grant money. Grants aren’t “free money.” They come with heavy reporting, tracking, and sustainability implications, especially when funding priorities change.Short-term funding can create long-term harm. One-off programs that disappear after a grant ends can leave communities without continuity or support.Strategy, planning, and infrastructure matter more than ever. Especially in the current funding and political climate, nonprofits need clarity on their core value, not just reactive programming.Discovery calls are a burnout-prevention tool. Thoughtful sales and vetting conversations help ensure alignment before work begins, saving time and energy later.You’re allowed to slow down. Giving yourself permission to rest, recalibrate, and create space is not a failure–it’s a sustainability strategy.If you’d like to listen to Fatima’s episode, you can find it at the links below:  Apple Podcasts: https://podcasts.apple.com/us/podcast/from-burnout-to-boundaries-building-a-consulting/id1735641469?i=1000746870487 Spotify: https://open.spotify.com/episode/3QLiiFSXaJYfJbh4HmrEdd?si=GS7Gj271RQmR62pupql4mA YouTube: https://youtu.be/vNLaDSX1-XM?si=JphDJWaw0N_2FWz2 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

    25 min
  6. #107: From Burnout to Boundaries: Building a Consulting Practice for the Long Haul

    JAN 27

    #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 current political climate and funding uncertainty are affecting mission-driven work, then pivot into practical ways consultants can prevent burnout, set boundaries, and “vibe check” clients before signing contracts. Listen if you’re doing nonprofit, policy, advocacy, or equity-adjacent work right now and you’re trying to stay sustainable without turning into a crispy little burnout crouton. Some of our favorite takeaways from this episode include:  The work isn’t separate from the political moment. Even when funding cuts or DEI backlash don’t hit you directly, the fear/uncertainty still seeps into daily operations and decision-making.Nonprofits are tightening budgets, so consulting sales cycles can slow down. Fatima notes it’s harder to get in front of decision makers and new work can take longer to close, even when need is high.Sustainability is a practice, not a one-time reset. Burnout prevention isn’t just “take a break.” It’s ongoing internal work to challenge grind-culture conditioning and perfectionism.A clear client capacity number is powerful. Fatima’s current sweet spot: 3 active engagements (typically 2 deep/long-term + 1 smaller side project/training).Boundaries are systems + mindset. Time-blocking by client, setting email response expectations, building buffer time, and protecting Fridays for business development help keep the work humane.Co-creation is messy because teams are different (and that’s normal). When a facilitation activity doesn’t land, Fatima treats it as data: there’s usually an unspoken barrier underneath that needs addressing.Not all money is good money. The group reinforces that taking misaligned work can cost more in energy, time, and missed opportunities than it’s worth.Guest & Host Information: Guest, Fatima Jawaid Marty, Owner/Founder of FJM ConsultingCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Fatima: Visit her website: https://fjmstrategy.comOn LinkedIn: https://www.linkedin.com/in/fatima-jawaid-marty Connect with us: YouTube: https://www.youtube.com/@TaketheLeap-Today Instagram: https://www.instagram.com/taketheleap_today 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

    1 hr

  7. JAN 22

    #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. They also share a few practical “we’ve been there” examples (hello, dead laptop) and talk through how entrepreneurs can reduce money stress without pretending cash flow is always predictable. Listen if you’re a business owner who knows you should be doing certain money things… and would like to stop feeling personally attacked by your own to-do list.  Key Takeaways from the Episode:  Emergency savings and a rainy day fund are important for business and your family. Julie’s reminder lands hard: business emergencies happen (laptops die, tech fails, life happens), and a dedicated buffer can keep you from panic-spending.Automation is the cheat code. Ashlan shares a system where a percentage of every invoice payment automatically moves into business savings, so it grows without extra willpower.Take action instead of spiraling. Ashlan calls out the trap of doing nothing when finances feel shaky and reframes it as: make a plan, take a calculated step, adjust as you go.Multiple income streams can reduce stress during transitions. They validate Julie’s advice that side gigs (or a bridge plan) can help entrepreneurs build stability, especially when startup costs are low for service-based businesses.Not all businesses have the same financial runway needs. They highlight how service-based, online businesses often have lower overhead than brick-and-mortar ventures, which changes what “safe to start” looks like.If you’d like to listen to Julie’s episode, you can find it at the links below:  Apple Podcasts: https://podcasts.apple.com/us/podcast/your-money-mindset-is-an-important-business-strategy/id1735641469?i=1000745906449Spotify: https://open.spotify.com/episode/4vqz4lxWtDv5AywIAXgNP6?si=DYr2S8PJSr-hTfsdi015xgYouTube: https://youtu.be/enhcireRdfw?si=ZWBUlkGF5jbsHE0jHost information: Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect: YouTube: https://www.youtube.com/@TaketheLeap-Today Instagram: https://www.instagram.com/taketheleap_today Ashlan:https://www.instagram.com/ashbeanpdxmktg https://www.linkedin.com/in/ashlan-glazier-anderson 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

    23 min
  8. #105: Your Money Mindset is an Important Business Strategy with Julie Stair

    JAN 20

    #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 money journey: getting out of debt, getting back into debt, navigating divorce, and rebuilding financially and then turning all of that into a coaching business. Listen if you want practical, doable steps for getting out of financial overwhelm (without shame), plus a refreshing reminder that money management isn’t “one size fits all.” Some of our favorite takeaways from this episode include:  Money coaching isn’t one-size-fits-all. Your background, responsibilities, and realities matter, especially for women and single moms.Don’t rely on networking as your only marketing plan. It’s valuable, but it’s a long game, and too many 1:1s can become a time sink.Start with an emergency fund before attacking debt. Without it, every unexpected expense becomes another trip back to the credit card.Mindset drives behavior. Many financial patterns come from what we’ve learned (or survived), not from a lack of intelligence.Service-based business owners: avoid starting your business in debt if you can. The lower your overhead, the easier it is to grow without financial panic.Guest & Host Information: Guest, Julie Stair, Founder of Gemini Financial Wellness and Moxie and Might Money CoachingCo-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX MarketingCo-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing StrategiesConnect with Julie: Visit her Website: http://www.geminifinancialwellness.com/ On Facebook: https://www.facebook.com/GeminiFinancialWellness On Instagram: https://www.instagram.com/moxieandmightmoneycoaching 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

    33 min
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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
    137
  • Rating
    Explicit
  • Copyright
    © 2026 Take The Leap
  • Show Website
    Take The Leap