Take The Leap

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 experience in fundraising, leadership, and nonprofit strategy and turned it into a business focused on helping organizations become more connected, sustainable, and human-centered. From launching The Savvy Fundraiser during maternity leave to writing a book, hosting a podcast, and building the Lead With Heart Summit, Haley’s story is a reminder that entrepreneurship can be both deeply personal and powerfully mission-driven.

We also dig into nonprofit burnout, the danger of reactive leadership, why diversified funding matters more than ever, and how boundaries, clarity, and emotional connection can transform both organizations and the people leading them.

Key Takeaways

• Entrepreneurship can be the bridge between ambition and a life that actually works. Haley built The Savvy Fundraiser because traditional work structures no longer matched the reality of being a parent, a leader, and a human being with limits.
• Burnout is not a personal failure, it is often a systems problem. Haley’s work centers on helping nonprofit leaders build healthier cultures where people feel connected, supported, and able to do meaningful work without constantly operating in survival mode.
• Saying yes to everything is not a growth strategy. Early in business, Haley took on too many kinds of work from a scarcity mindset. One of her biggest lessons was learning that clarity, boundaries, and focus create more sustainable success than being everything to everyone.
• Your business should be designed on purpose, not built by default. Haley talked about the importance of choosing offers, projects, and platforms strategically instead of piling things on just because there is an opportunity or because someone else is doing it.
• People do not leave missions, they leave unhealthy cultures. One of the strongest ideas in this episode is that nonprofits can only thrive when the humans behind the mission feel safe, valued, and supported.

Guest & Host Information: 

• Guest, Haley Cooper, Founder of The Savvy Fundraiser
• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies

Connect with Haley:

• Website: www.thesavvyfundraiser.com 
• LinkedIn: https://www.linkedin.com/in/haley-cooper-cfre 
• Lead with Heart Summit on April 16 & 17: https://leadwithheart.vfairs.com

Connect with us:

• On YouTube: https://www.youtube.com/@TaketheLeap-Today 
• On Instagram: https://www.instagram.com/taketheleap_today 

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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 leads to more sales. 

Spoiler alert…it doesn’t. We’re sharing real examples (including clients with tens of thousands of followers and zero engagement) to show why audience quality matters more than audience size, and how focusing on the wrong metrics can stall your growth. We also dive into what it takes to build a loyal, engaged audience, from creating two-way conversations to being intentional about where and who you are networking with. 

If you’ve ever felt like your marketing “should be working” but isn’t, this episode will help you zoom out, reassess your foundation, and focus on what actually moves the needle. 

Key Takeaways

• A small, engaged audience will always outperform a large, disengaged one. Vanity metrics don’t pay your bills, but action does. 100 true fans who buy is better than 10,000 followers who scroll past.
• If your audience isn’t converting, it’s probably not your offer…it might be your people. The wrong audience (or fake followers 👀) will make even great products look like failures.
• You can’t skip the foundation and expect marketing to work. Ads, content, and funnels won’t fix a business that doesn’t clearly know who it’s for.
• Engagement is not optional, it’s the name of the game. Building a true fan base requires participation, not just posting. If you’re not responding, interacting, and involving your audience, they won’t stick around.
• Stop chasing “more” and start focusing on “right.” More followers, more emails, more reach means nothing if they’re not aligned with your business.
• Strategic networking beats random networking. The question isn’t “Where can I go?” but rather, “Where are my people already showing up?”

This episode references our conversation with Megan Eckman, episode #121 on Apple Podcasts, Spotify, and YouTube. You can catch our first episode with Megan #062.

Host information:

• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-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?

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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 why it’s costing them time, money, and momentum.

Spoiler: it’s not your logo, your website, or your ads. It’s your audience. Megan breaks down why building a fan base before you launch is the difference between crickets… and a stadium full of people ready to buy. We also get into her new subscription-based storytelling business (honestly, we’re obsessed), how she’s monetizing from day one, and why “passive income” is mostly a myth.

Key Takeaways: 

• You don’t have a marketing problem…you have an audience problem. If you don’t know who you’re building for (beyond vague demographics), nothing you do will consistently convert.
• Build the fan base before the launch, not after. Waiting until you have a product to “start marketing” is backwards and one of the biggest reasons launches flop.
• Loyal super fans beat a larger audience. You don’t need thousands of people, but you need the right people who are engaged, invested, and ready to buy (and tell others).
• “Passive income” is mostly a fantasy. If you don’t care about the people you’re serving, it shows, and no amount of funnels or ads will fix that.
• Marketing without a foundation = wasted money. Running ads or pushing content without knowing your audience is basically lighting your budget on fire.
• Engagement is a two-way street. A real audience isn’t just consuming. They’re interacting, responding, and feeling like part of what you’re building.
• Not all networking is created equal. If you’re in rooms full of people just like you, you’re not finding clients, but you can make industry friends.
• You need to know where your people actually are. The right rooms (online or in-person) matter more than the number of rooms you’re in.
• Consistency beats intensity. Whether it’s content, networking, or audience building, doing it regularly over time is what creates real traction.

Guest & Host Information:

• Guest, Megan  Eckman, Founder of Fat Cap Design and Creator of PDX Spellbound
• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies

Connect with Megan:

• Join PDX Spellbound: https://pdxspellbound.com 
• Website: https://www.fatcap-design.com 
• Find Your First 100 Fans strategy session: https://www.fatcap-design.com/find-your-fans 
• Instagram: https://www.instagram.com/pdx_spellbound 
• Listen to The Awkward Handshake, a new podcast: https://www.buzzsprout.com/2574078 

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?

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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 community-centered food growing through Hearth & Hollow, and how that shift was not a random reinvention so much as stepping fully into work that matches her values.

They also unpack why community is more than a buzzword right now, how local action can be a real form of resistance, and why pivots in business often come from paying attention to what keeps pulling at you. Plus: networking in Vegas versus Portland, garden dreams, and the usual media recs.

If you’ve been feeling the nudge to change direction in your business, this episode is a good reminder that a pivot does not mean you failed. It often means you finally listened.

Key Takeaways

• A pivot can be alignment, not abandonment. Dusti’s shift into Hearth & Hollow shows how a business evolution can build on everything you already know instead of tossing it out.
• Your past work still counts. Marketing, relationship-building, and community skills all transferred into Dusti’s new venture in a meaningful way.
• Community really is the strategy. Whether that means growing food, showing up locally, or simply knowing your neighbors, local connection matters.
• You do not have to do everything. Everyone’s role in community care and resistance will look different, and that is okay.
• In-person connection still matters. Networking, collaboration, and shared spaces keep opening doors, even when schedules get messy.

This episode references our conversation with Dusti Arab, episode #119 on Apple Podcasts, Spotify, and YouTube. You can catch our first episode with Dusti #060.

Host information:

• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-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?

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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 & Hollow
• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies

Connect with Dusti:

• On Instagram: https://www.instagram.com/dustiarab 
• On LinkedIn: https://www.linkedin.com/in/dustiarab 
• On Substack: https://dustiarab.substack.com
• On 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?

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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 Marketing
• Co-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
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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 Projects
• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies

Connect 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
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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 Marketing
• Co-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
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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 Connection
• Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
• Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies

Connect with Brady:

• On https://www.linkedin.com/in/bradyhelkenn
• Visit BH Tech Connection: https://bhtechconnection.com 
• Visit Deluxe Sabers: https://www.deluxesabers.com
• Grab 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

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 Marketing
• Co-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