Behind Their Success: Advice For Entrepreneurs

What if the secret to building wealth, health, and freedom wasn’t in a quick fix, but in compounding small decisions over time? Today’s episode will light a fire under every small business owner and entrepreneur who wants to grow their business and their life at the same time. In this conversation, I sit down with Mike Milligan, founder of Ideas by Mike and 1.Oak Financial. Mike’s journey started at his grandmother’s dining room table, selling collared sandwiches at construction sites, and has grown into decades of helping entrepreneurs create purpose-driven wealth. We dive into: Mike’s personal health transformation—losing over 100 pounds by “planning his health like his money.” The lessons he learned from his grandmother that shaped his entrepreneur mindset. Why compounding small actions is the real way to grow your business and yourself. The advantages and challenges of living and running a business in Puerto Rico (and the tax strategies behind it). The critical difference between a tax preparer and a true tax planner. Why entrepreneurs must pay themselves first and learn to own their business—instead of letting their business own them. If you’re an entrepreneur chasing personal development while trying to grow your business, this episode is packed with wisdom and practical steps. Connect with Mike: – COMING SOON: his books The One-of-a-Kind Financial Plan and Retirement Déjà Vu 👉 Website: www.1oakfinancial.com Follow Mike on LinkedIn: https://www.linkedin.com/in/mikemilligancfp/ Are you a small business owner tired of overpaying the IRS? Here’s the truth: most CPAs are historians—they file what already happened. But real money is saved through tax planning, not tax prep. At Squires Tax Planning, we work with entrepreneurs and high-income earners to legally and ethically minimize taxes. We’ve saved clients hundreds of thousands of dollars through strategies their previous preparer never mentioned. ✅ Take our free tax assessment at squirestaxplanning.com to see if you’re likely overpaying. ✅ Book a free discovery call and find out how much tax you can save this year. If this episode brought you value, do me a favor: rate, review, and share the podcast. That’s how we keep helping entrepreneurs become healthier, wealthier, and wiser. And connect with me on social media or at paydensquires.com where I share daily tips on entrepreneurship and personal development. Mike Milligan is an investment advisor representative of Advisory Alpha, LLC, a SEC registered investment advisor. All opinions expressed by Mike Milligan are solely his own opinions and do not reflect the opinions of Advisory Alpha, LLC, and as such, any and all statements of purported or observed general practices of non-affiliated firms and advisors; conditions of the broad financial services industry; or performance or returns with regards to products, securities, markets, or otherwise, whether or not advisor indicates they may be relying on third-party data or sources, are solely the opinions and/or interpretations of the advisor and are not intended to be offered as factual. The validity of these statements has not been verified, and as such, no representations of their validity are made. This recording is for informational purposes only and should not be relied upon for investment decisions. Investment advisory and financial planning services offered through Advisory Alpha, LLC, a Registered Investment Advisor. Insurance, coaching, and education services offered through Ideas by Mike, LLC, DBA 1.oak Financial. Ideas by Mike, LLC, DBA 1.oak Financial, Paden Squires - Behind Their Success Podcast are separate and unaffiliated entities from Advisory Alpha, LLC. While tax and legal issues may be discussed in the general course of financial and investment planning, Advisory Alpha does not provide tax or legal services.

Ever feel like you’re grinding in your business but not really growing it? Today’s episode is for you. I sat down with Eric Brotman — Certified Financial Planner, CEO of BFG Financial Advisors, author, and host of Don’t Retire...Graduate! With over 25 years of experience helping entrepreneurs and families achieve financial freedom, Eric brings the kind of wisdom you can’t Google. We talk about: Why the first 5 years of entrepreneurship usually suck (and why that’s the entry fee). How to work on your business, not just in it. Playing to your strengths vs. fixing weaknesses — and why joy in your work matters more than money. Redefining success: from survival → growth → impact. The mindset shifts every entrepreneur needs for long-term business growth and personal development. Eric’s story is a masterclass in entrepreneurship, leadership, and financial planning. Whether you’re just starting out, scaling your firm, or thinking about succession, you’ll walk away with practical insight and a renewed drive to keep building. 🎧 Tune in and hear why success isn’t just about wealth, it’s about creating freedom and impact — in business and in life. Squires Tax Planning – Stop Overpaying the IRS A quick reminder — most entrepreneurs aren’t working with a tax planner, they’re working with a tax preparer. There’s a huge difference. At Squires Tax Planning, we specialize in helping entrepreneurs and high-income earners pay the least amount of income taxes legally possible. Our clients have saved hundreds of thousands of dollars by implementing proactive strategies their old preparer never mentioned. If you’re serious about business growth, personal development, and building long-term wealth, you need to be intentional about your tax plan. 👉 Take our free assessment at squirestaxplanning.com to see if you’re overpaying. You can also book a free discovery call with our team to learn how strategic tax planning can accelerate your financial freedom. Connect with Eric Brotman: Podcast: Don’t Retire, Graduate Book: Don’t Retire...Graduate! Website: BFG Financial Advisors 👉 If you found this episode valuable, do me a huge favor: rate, review, and share the podcast. That’s the best way to help us reach more entrepreneurs who are chasing growth and personal development. Follow me, Paden Squires, for more tips on entrepreneurship, business growth, and tax planning strategies: Website: squirestaxplanning.com Instagram / LinkedIn: @padensquires Let’s keep building healthy, wealthy, and wise entrepreneurs.

Avoiding mistakes is priceless. If you’re a small business owner, entrepreneur, or high achiever chasing personal development and growth, this conversation is going to hit home. I sat down with William Holsten—a seasoned entrepreneur, inventor, bestselling author, and the “Business Mistake Prevention Specialist.” With nearly 40 years in global marketing and innovation plus his own entrepreneurial ventures (including a patented carnival game that’s still around today), William has seen it all—the wins, the setbacks, and the costly mistakes. We dive into: The biggest preventable mistakes entrepreneurs make and how to spot them early How to “goof proof” your business with William’s 10 practical tools Why self-awareness might be the #1 superpower for small business owners The underrated role of structure and planning in fueling creativity and long-term success How reframing your perspective (like Charlie Munger’s “invert” principle) can save your business from disaster This episode is full of small business tips and strategies you can put into practice today. If you’re serious about growth, scaling, and protecting your business from “uh oh” moments, you’ll want to take notes. Connect with William Holsten 👉 Visit williamholsten.com to grab his free $10,000 Mistake Checklist and learn more about his work helping entrepreneurs avoid costly blunders. Let’s Talk Taxes And hey—if you’re an entrepreneur or high-income earner, here’s the deal: most business owners are overpaying in taxes because they’ve got a tax preparer, not a tax planner. That’s where I come in. At Squires Tax Planning, we work alongside small business owners and high achievers to proactively plan, legally minimize taxes, and keep more of your hard-earned money. 👉 Take our free assessment at squirestaxplanning.com to see if you’re leaving money on the table. From there, you can book a free discovery call with my team and me. Final Note If this episode helped you, please rate, review, and share the podcast. That’s the best way to help us reach more entrepreneurs and keep building a community of healthy, wealthy, and wise leaders.

It's our 100th EPISODE! Today we are talking about six lessons every Entrepreneur needs to hear after interviewing 100 entrepreneurs. After sitting down with over a hundred risk-takers, game-changers, and trailblazers, I’ve pulled together my top six lessons that will completely shift the way you think about business. If you’re an entrepreneur or small business owner looking for real business tips that go beyond the Instagram fluff, this one’s for you. In this milestone episode of Behind Their Success, I’m pulling back the curtain on the most powerful takeaways from our first 100 episodes—things I wish I knew when I was just starting out. We’re talking: 1️⃣ Think Bigger Than You Think is Possible – stop capping your dreams at your current abilities. 2️⃣ Build Systems, Not Just Skill – the real secret to scaling. 3️⃣ Purpose Over Profits – why alignment fuels longevity. 4️⃣ Become a Decision Maker, Not Just a Doer – escape the daily grind. 5️⃣ Embrace Continuous Learning & Humility – stay coachable to stay ahead. 6️⃣ Say Yes Early, Say No Later – the art of focus as you grow. Whether you’re grinding from your living room or running a multi-million-dollar company, these lessons apply. And trust me—they’ve been tested by the best in the business. 💡 CALL TO ACTION: If you’re tired of overpaying taxes and want a CPA who actually helps you strategically keep more of your money, head over to SquiresTaxPlanning.com. Take our free assessment, find out if you’re overpaying, and let’s put some money back in your pocket—legally and ethically. 📲 Follow me on Instagram @PadenSquires for more entrepreneur insights, small business tips, and behind-the-scenes of running a business. 🎧 Listen now and let’s make your next 100 moves count.

Everybody wants the big wins—but nobody talks about the boring part. The slow, unsexy grind. The daily reps. The posts nobody sees. The podcast episodes that only get 12 downloads. But that’s where the magic happens. That’s compounding—and it’s everything. In this episode, I sit down with Portland startup, Rick Turoczy, and we dive into how showing up consistently in business, in relationships, and in content leads to explosive long-term growth. Rick shares what it really takes to build strong entrepreneurial communities, how failure is just data, and why putting yourself out there—even when it’s rough—is the only way to break through. Whether you’re a solo founder, small business owner, or just getting into personal development, this one hits deep. Rick drops straight wisdom on mindset, vulnerability, and why playing the long game—brick by brick—is what actually works. What You’ll Learn: Why community is a non-negotiable for entrepreneurs The myth of the “overnight success” and what really goes down How failure is just your First Attempt In Learning (F.A.I.L.) Why personal development must precede business growth How to start putting yourself out there—even if you suck at first Connect with Rick: Check out Rick’s work and writing on the Silicon Florist blog and learn more about the Portland Incubator Experiment (PIE). You’ll see exactly how he's shaping the future of entrepreneurship in the PNW. 👉 https://www.siliconflorist.com 🙌 Connect with Paden: If you want high-level tax strategy that keeps more money in your pocket and helps scale your business: 📍 squirestaxplanning.com 🎯 Take the free tax savings assessment 📞 Book your free tax discovery call Follow Paden on social for tips on entrepreneurship, money, and mindset: 📱 Instagram + LinkedIn: @PadenSquires 🌐 padensquires.com

Are you building your business to sell—or just to survive? In today’s episode of Behind Their Success, I sit down with the powerhouse himself, Sal Tirabassi—a seasoned fractional CFO, private equity investor, and the guy behind CFO Pro + Analytics. With over $400 million raised and decades of experience helping high-growth companies, Sal breaks down what most entrepreneurs get wrong about preparing for an exit—and how to fix it before you leave millions on the table. Whether you're a small business owner with an eye on retirement or you're dreaming of your first big exit, this one’s for you. 💡 What You’ll Learn in This Episode: ✅ Why clean, explainable financials are the foundation of every great business exit strategy ✅ How mom-and-pop shops can level up and avoid leaving value behind ✅ The real ROI of professionalizing your finance function before you sell ✅ What investors really want to see during due diligence ✅ The biggest mindset shift founders need when seeking capital ✅ The power of 13-week cash flow modeling for clarity and confidence ✅ Real-world strategies to turn chaos into systems—and dollars 📌 SEO Highlights: We go deep on: Small business exit strategies that actually increase valuation How to sell a business without scaring off investors Business exit planning tips that lead to real equity value What "due diligence readiness" really means (hint: it’s not QuickBooks and hope) 🔧 Tools & Tactical Takeaways: Sal gives tactical advice on: Building a sellable business with equity value in mind Implementing automation and fractional CFO services for lean growth Using AI tools (like note takers and SOP generators) to scale like a pro Dealing with cash flow crunches and investor skepticism with strategy, not stress 🚀 Connect with Sal Tirabassi: 🌐 Website: cfoproanalytics.com 🔗 LinkedIn: Just search Sal Tirabassi 🧮 Free Tools: Check out the equity dilution and CAC calculators on the website 🔥 Ready to stop overpaying taxes? I help entrepreneurs and high-income earners legally and ethically reduce their tax bills—guaranteed. Head over to squirestaxplanning.com to take our free assessment and see how much you might be leaving on the table. 🙌 If You Found Value… Please rate, review, and share the podcast. That’s the best way to help us grow and continue serving healthy, wealthy, and wise entrepreneurs like you. You can follow me on social media or head to padensquires.com for more tools, thoughts, and behind-the-scenes content.

Today I sit down with Jeremy Jenson — founder & CEO of Encore Search Partners — to talk about how to scale your business by building systems, hiring the right people, and becoming a real-deal leader who stops being the bottleneck in their own company. Jeremy went from launching a scrappy lead-gen firm to running the largest executive search firm in Houston. He shares exactly how he made the leap, what scaling really looks like behind the scenes, and the mindset shifts founders must embrace to level up. No fluff, just the real playbook from a founder who's been there. 🎯 What You’ll Learn in This Episode: How Jeremy scaled from $250K in revenue to $15M+ by shifting his business model and investing in the right people Why many founders stall out — and how to break free from being the only person making decisions The power of hiring a COO and implementing EOS to unlock growth How to hire and compensate A-players — and why your old comp models are holding you back Building a business around systems (not people) to protect scalability and long-term value Jeremy’s take on AI, offshoring, and the future of professional services — and how to stay ahead of it The mindset shift from being the smartest person in the room to being the leader who attracts the smartest people Scaling tips for entrepreneurs feeling stuck around the $1M revenue mark 🚀 Perfect For: Entrepreneurs, founders, and small business owners who are looking for tactical advice on how to scale their business, hire effectively, build systems, and shift from operator to CEO. 🔗 Connect with Jeremy Jenson: 🔹 LinkedIn: Jeremy Jenson (look for the 🐐 in the name!) 🔹 Instagram: @jeremyjenson — behind-the-scenes, leadership gems, and a little bit of life 🔹 Encore Search Partners: encoresearch.com 📣 Call to Action: Enjoyed the episode? Don’t forget to rate, review, and share it with another entrepreneur who’s ready to scale their business. It’s how we spread the word and help more people build a business that works without them. You can also follow me (Paden Squires) at: 🌐 padensquires.com 📲 Instagram & LinkedIn @padensquires 💼 For tax strategy and planning: squirestaxplanning.com

Ever feel like your brain’s running a thousand tabs at once—but none of them are actually helping you move forward? You're not alone. In this episode, we dig into how stillness, flow, and a bit of strategic brain-dumping can be the ultimate performance hack for entrepreneurs and high achievers who are stuck in their own mental clutter. I sat down with Reuven Shelef—executive coach, organizational whisperer, and founder of Out of the Box Consulting—to unpack how to get clarity, simplify complexity, and build a life that’s not just productive… but powerful. This episode isn’t about theory—it’s packed with real, practical tools from a guy who's coached Fortune 500 execs and built systems that fuse engineering, military, and deep spiritual wisdom into one methodology for transformation. Whether you’re a hard-charging entrepreneur or a leader trying to bring more clarity into the chaos—this one’s for you. 🎯 What We Cover: Why most problems are mental clutter—and how to start untangling complexity How entrepreneurs can use “brain dumps” to create clarity and momentum What flow state really is, and how to access it without sitting cross-legged for 30 minutes The surprising meditation practice that got Reuven started Tools for high achievers who “can’t sit still” but desperately need stillness Using the body to hack the mind (hot springs, saunas, and float tanks included) Aligning personal life and business—because there’s no real separation How to fix the cross-functional chaos that kills startups and big orgs alike 📌 Connect with Reuven: 🌐 Website: ReuvenShelef.com 📅 Book a free call: MeetReuven.com ⚡️ Call to Action: If you’re a business owner, entrepreneur, or just a hard charger trying to bring more clarity, alignment, and flow into your life—do yourself a favor: listen to this episode. Then hit pause, grab a notebook, and do nothing for 15 minutes. See what happens. 🧠 Ready to build a business and a life that actually works together? Subscribe, leave a review, and share this episode with a fellow high achiever who needs to hear it. Want to save thousands in taxes while building the business of your dreams? 👀 Take the free assessment at squirestaxplanning.com