The Compassionate Capitalist™ Show with Karen Rands

• Crypto, the IRS, and the Hidden Tax Storm Ahead with Janna Scott

  As I talk with entrepreneurs and investors, I’m often struck by how many people underestimate the risks tied to crypto investing, especially when it comes to taxes. Right now, the IRS has slowed down audits, but that doesn’t mean the storm has passed. It’s just gathering strength.Today, I sit down with Janna Scott, founder of DeFi Tax, to pull back the curtain on what’s really happening with crypto tax reporting. Janna shares how she uncovered major flaws in widely-used tax software, why exchange statements can’t be trusted, and how compounded penalties can turn a small mistake into a devastating financial burden.What I love about Janna’s approach is that she not only sounds the alarm, she has built a blockchain-first solution that ensures accuracy, audit-readiness, and peace of mind.Whether you’ve dabbled in crypto, trade regularly, or run a business that accepts crypto payments, this conversation is your wake-up call to get prepared before the IRS comes knocking.TakeawaysPopular crypto tax tools often produce wildly different results (35–120% variance).Exchanges disclaim responsibility for tax reporting errors, leaving investors liable.The IRS already has access to transaction data through John Doe summons.Penalties and compounding interest can double or triple liabilities over time.State tax authorities are often more aggressive than the IRS.Middle-class investors are the most vulnerable when audits restart.DeFi Tax uses blockchain data directly, providing audit-ready transparency.Having expert representation can mean the difference between resolution and ruin.Chapters00:00 Introduction: Why crypto investors face unseen risks04:12 How Janna discovered errors in crypto tax software08:45 Why blockchain is the only reliable source of truth15:30 The IRS admits flawed audits; but investors still pay27:00 Compounding penalties and the impact on middle-class investors38:50 State-level tax risks and aggressive enforcement46:10 How DeFi Tax partners with CPAs and defends audits53:39 Why crypto taxes (and the IRS) are here to stay56:08 Final advice: don’t wait for the IRS storm to arriveAbout Janna ScottJanna Scott is a powerhouse in the world of crypto tax compliance and the founder of DeFi Tax. She has worked directly with the IRS and SEC, building DeFi Tax to bring clarity, automation, and audit-readiness to the chaos of crypto profit/loss reporting for tax purposes. Through her tax accounting services and her innovative AI/Blockchain application platform, Janna helps users stay ahead of shifting regulations and out of trouble with the IRS.🔗 Learn more at defitax.usAbout Karen RandsI'm Karen Rands, founder of the Compassionate Capitalist Movement. I help entrepreneurs prepare to raise capital the smart way and guide investors in identifying startup opportunities that build wealth and make a difference. This show is your roadmap to funding success, from pitch deck to public offering.📅 Want expert feedback on your pitch? Book a consult with me: bit.ly/KCHcalendar 🔗 Learn more: karenrands.co 🎧 Catch more episodes: thecompassionatecapitalistshow.com 📘 Free eBook: The 4 Ws of Crowdfund Investing: https://bit.ly/FreeCrowdfundInvestingBook 🎓 Join the Academy: bit.ly/CA-prelaunch

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• Book Launch and Compassionalist Academy Reimagined with Karen Rands

  In this episode, I share how everyday people can grow wealth and create impact through equity crowdfunding. Drawing from my new book Inside Secrets to Crowdfund Investing: Follow Jane’s Journey, I break down the myths that hold people back from angel investing and show how a diversified, consistent approach can build generational wealth.You’ll meet “Jane,” a relatable mid-career professional who discovers how to shift from risky real estate to smart startup investing. I also introduce the Compassionate Capitalist Academy, which provides a roadmap for anyone ready to turn passion and purpose into profit.If you’ve ever thought you’re too old, too busy, or don’t have enough money to invest in entrepreneurs, this conversation will change your perspective.Key TakeawaysEquity crowdfunding makes angel investing accessible to everyone, starting with as little as $100.Diversification and consistency are the keys to long-term portfolio success.Common false beliefs, like “I don’t know enough,” “I don’t have time,” or “I don’t have enough money” are myths that hold people back.You don’t need to quit your job to build wealth; you can start small and grow.Real estate isn’t the only path; investing in entrepreneurs can often yield greater impact and returns.The Compassionate Capitalist Academy and my books offer step-by-step frameworks for new investors.Chapters00:00 – Introduction: The power of compassionate capitalism03:18 – Why invest in entrepreneurs instead of real estate07:42 – Jane’s story: a mid-career professional’s path to angel investing12:55 – The myths of investing: “I don’t know enough,” “I don’t have time,” “I don’t have money”19:10 – Building wealth through diversification and consistency23:37 – From false beliefs to proven frameworks: overcoming barriers28:05 – How the Compassionate Capitalist Academy supports new investors32:21 – Inside Secrets to Crowdfund Investing: making angel investing relatable36:54 – Promo details: book launch, course discounts, and special codes41:30 – Call to action: start small, start today, and build your wealth legacy45:12 – Closing thoughtsAbout Karen RandsI'm Karen Rands, founder of the Compassionate Capitalist Movement. I help entrepreneurs prepare to raise capital the smart way and guide investors in identifying startup opportunities that build wealth and make a difference. This show is your roadmap to funding success, from pitch deck to public offering.📅 Want expert feedback on your pitch? Book a consult with me: bit.ly/KCHcalendar 🔗 Learn more: karenrands.co 🎧 Catch more episodes: thecompassionatecapitalistshow.com 📘 Free eBook: The 4 Ws of Crowdfund Investing: https://bit.ly/FreeCrowdfundInvestingBook 🎓 Join the Academy: bit.ly/CA-prelaunch

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• Raising Capital With Equity Crowdfunding Featuring Karl Dakin

  Raising capital is one of the biggest hurdles for entrepreneurs. Many capital raising campaigns fail because founders fall into common traps.In this episode of the Compassionate Capitalist™ show, I talk with Karl Dakin, Founder of Dakin Capital, about what it really takes to succeed. We clear up the myths around crowdfunding and share practical strategies entrepreneurs can use to connect with investors.Karl explains his Know, Trust, and Buy framework, helping founders build credibility so investors feel secure, making returns the “icing on the cake.”We also explore Reg CF, Reg D 506(c), and Reg A+, what they are, how they’ve evolved, and why Reg D 506(c) has become a hot tool for attracting high-net-worth investors.Entrepreneurs will learn how to:Craft pitches that inspire confidence.Build trust with transparency and storytelling.Leverage social media to drive momentum.Whether you’re new to crowdfunding or experienced, this conversation gives you actionable insights to raise capital with strategy and confidence.TakeawaysCrowdfunding is a powerful tool for raising capital.The potential of crowdfunding is still largely untapped.Understanding the different types of crowdfunding is crucial for entrepreneurs.Customers can be valuable investors in crowdfunding campaigns.Reg CF allows non-accredited investors to participate in funding.Building a crowd before launching a campaign is essential for success.Reg D 506C offers flexibility for accredited investors.Reg A+ provides opportunities for larger fundraising efforts.The cost of raising capital through crowdfunding can be significant.Investors should conduct due diligence before investing in crowdfunding campaigns.Chapters00:00 Introduction to Equity Crowdfunding04:00 The Evolution of Crowdfunding and Its Potential09:50 Karl Dakin's Journey into Crowdfunding16:35 Understanding Different Types of Crowdfunding21:10 The Importance of Community in Crowdfunding27:19 Navigating the Interstate Exemption30:35 Reg CF: The Sweet Spot of Crowdfunding38:56 Understanding Regulation A and 506C41:44 The Wild West of 506C Offerings45:28 Strategies for Raising Capital54:11 Exploring Regulation A+57:15 The Importance of Due Diligence in Crowdfunding01:09:29 Customer-Centric Investment StrategiesAbout Karl DakinKarl Dakin is the Founder and Operator of Dakin Capital, LLC, where he guides entrepreneurs in raising capital through equity crowdfunding. With decades of experience as a Startup Business Designer and Growth Strategist, Karl offers proven methods that combine investor psychology, compliance, and practical fundraising tactics.Learn more at dakincapital.comAbout Karen RandsI'm Karen Rands, founder of the Compassionate Capitalist Movement. I help entrepreneurs prepare to raise capital the smart way and guide investors in identifying startup opportunities that build wealth and make a difference. This show is your roadmap to funding success, from pitch deck to public offering.📅 Want expert feedback on your pitch? Book a consult with me: bit.ly/KCHcalendar 🔗 Learn more: karenrands.co 🎧 Catch more episodes: thecompassionatecapitalistshow.com 📘 Free eBook: The 4 Ws of Crowdfund Investing: https://bit.ly/FreeCrowdfundInvestingBook 🎓 Join the Academy: bit.ly/CA-prelaunch

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• Sig Said Yes! Learn Angel Investing from a Top Compassionate Capitalist

  If you’ve ever wondered how angel investing works, this episode is for you.On this episode of the Compassionate Capitalist™ show, I’m joined by my cohost Erik Nelson for a conversation with Sig Mosley, the “Godfather of Angel Investing” in Atlanta. From his early days at MSA to completing over 200 angel investments, Sig has built a legacy as an investor and a champion of compassionate capitalism, using investment to uplift communities.We explore his views on what makes a founder worth backing, why supporting underrepresented entrepreneurs is smart business, and how angel investors drive innovation and growth. Sig also shares insights on market awareness, smart risk-taking, and the next generation of investors.Packed with wisdom, real-world stories, and a few laughs, this episode offers actionable insights whether you’re starting your investing journey or preparing to pitch.Key TakeawaysSig Mosley is a leading figure in compassionate capitalism.Angel investing requires a willingness to take risks.Successful founders are coachable and open to feedback.Understanding the market and competition is crucial for startups.Investors should diversify their portfolios to mitigate risk.The future of angel investing lies in engaging younger generations.Building relationships with entrepreneurs is key to successful investments.Investors need to invest in what they know and understand.Community impact is a significant aspect of angel investing.The economy relies on the growth of young companies supported by angel investors.Chapters00:00 Introduction to Compassionate Capitalism02:56 The Journey of Sig Mosley05:41 The Role of Angel Investing08:27 Identifying Coachable Founders11:35 Understanding Market Competition14:15 The Importance of Timing in Business17:17 Success Stories and Lessons Learned20:05 Reflections on Missed Opportunities31:21 Navigating Valuation and Relationships in Investments32:06 Mergers vs. IPOs: Insights from Experience32:55 The Landscape of Technology Companies in the South34:49 Cultural Influences on Southern Entrepreneurship35:45 Empowering Diverse Entrepreneurs in Atlanta39:31 Winding Down Mosley Ventures and Future Plans41:09 The SIGI Awards: Celebrating Angel Investors45:14 Encouraging Angel Investment in the Community54:12 Final Thoughts on Angel Investing and Community ImpactAbout Sig MosleySig Mosley, Managing Partner at Mosley Ventures, LLC, is known as the “Godfather of Angel Investing” in Atlanta. With over 200 angel investments, he has been a driving force in the Southeast’s startup ecosystem, promoting compassionate capitalism to deliver financial returns and community impact. Sig supports underrepresented founders, values coachability, and invests in companies with strong market potential.Learn more about Sig LinkedIn | www.mosleyventures.comAbout Erik NelsonErik Nelson is President of Coral Capital, Mountain Share Transfer, and Sterling Holdings. His teams specialize in helping private and public companies meet their compliance obligations and stay in good standing with regulatory agencies. Erik and I co-host the Capital Conversations podcast, where we unpack the strategies and realities of raising capital, going public, and managing investor relations.🔗 Learn more about Erik: LinkedIn | coralcapital.comAbout Karen RandsI'm Karen Rands, founder of the Compassionate Capitalist Movement. I help entrepreneurs prepare to raise capital the smart way and guide investors in identifying startup opportunities that build wealth and make a difference. This show is your roadmap to funding success—from pitch deck to public offering.📅 Want expert feedback on your pitch? Book a consult with me: bit.ly/KCHcalendar 🔗 Learn more: karenrands.co 🎧 Catch more episodes: thecompassionatecapitalistshow.com 📘 Free eBook: The 4 Ws of Crowdfund Investinghttps://bit.ly/FreeCrowdfundInvestingBook🎓 Join the Compassionalist Academy : bit.ly/CA-prelaunch

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• Let’s Talk Business Finance with Dominick Wallace

  In this episode of The Compassionate Capitalist™ Show, I’m joined by Dominick Wallace, a business lending expert, to answer key questions many entrepreneurs face: Should you borrow? What kind of funding? When’s the right time?We cover the three types of money businesses use to grow: investor capital, revenue, and debt. While investor funding often feels like the best route, we explain why smart use of debt can actually cost less in the long run and help you stay in control.Dominick and I talk about how using business credit, instead of your personal credit can make a big difference when applying for loans. And for those who already raised capital, using those funds to unlock a revolving credit line can give your business a cushion when cash flow dips.The truth is, another economic storm is coming. Don’t wait until it’s too late. Preparing now could be the difference between staying afloat and shutting down, just like many businesses experienced during the pandemic.If you're thinking about funding options or want to prepare for the unexpected, listen to this podcast and feel free to send in your questions.TakeawaysDebt serves a critical function when raising capital.Understanding different types of debt is crucial for entrepreneurs.Cash flow management is essential for business success.SBA loans can provide significant support for startups.Creative financing strategies can help overcome funding challenges.Establishing business credit is vital for future financing opportunities.Franchises often have more predictable revenue models.Insurance options are available for large orders to mitigate risk.The more risk involved in a deal, the higher the expected yield.Building a strong credit history can facilitate access to capital.Episode Chapters00:00 Understanding Access to Capital02:50 The Role of Debt in Business Growth05:30 Case Study: Financing Challenges and Solutions08:16 Job Costing and Profitability10:20 Improving Business Credit and Financial Health13:33 Purchase Order Financing Explained16:16 Navigating Contracts and Agreements19:07 Risks in Purchase Order Financing21:42 Insurance and Risk Management in Financing25:12 Understanding Insurance in Sports and Business26:13 Navigating SBA Loans for Startups28:15 The Importance of Debt Service Coverage Ratio33:37 Challenges with Government Debt and SBA Loans35:26 The Role of Government Guarantees in SBA Lending41:57 Franchises vs. Startups: Financing Perspectives47:32 Creative Financing Strategies for Real Estate53:50 Building Business Credit for Future SuccessAbout Dominick WallaceDominick Wallace is the Managing Director at Wallace Capital, where he helps entrepreneurs and business owners secure the funding they need to grow and scale. With deep expertise in commercial lending and strategic financing, Dominick guides clients through the smart use of debt, business credit, and capital planning. He’s committed to making access to funding clear, achievable, and aligned with long-term business success.About Karen RandsI'm Karen Rands, founder of the Compassionate Capitalist Movement. I help entrepreneurs prepare to raise capital the smart way and guide investors in identifying startup opportunities that build wealth and make a difference. This show is your roadmap to funding success—from pitch deck to public offering.📅 Want expert feedback on your pitch? Consult with me: bit.ly/KCHcalendar 🔗 Learn more: karenrands.co 🎧 Catch more episodes: thecompassionatecapitalistshow.com 📘 Free eBook: The 4 Ws of Crowdfund Investing, join the Academy: bit.ly/CA-prelaunch

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