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:
Whether you’re new to crowdfunding or experienced, this conversation gives you actionable insights to raise capital with strategy and confidence.
Takeaways
Crowdfunding 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.
Chapters
00:00 Introduction to Equity Crowdfunding
04:00 The Evolution of Crowdfunding and Its Potential
09:50 Karl Dakin's Journey into Crowdfunding
16:35 Understanding Different Types of Crowdfunding
21:10 The Importance of Community in Crowdfunding
27:19 Navigating the Interstate Exemption
30:35 Reg CF: The Sweet Spot of Crowdfunding
38:56 Understanding Regulation A and 506C
41:44 The Wild West of 506C Offerings
45:28 Strategies for Raising Capital
54:11 Exploring Regulation A+
57:15 The Importance of Due Diligence in Crowdfunding
01:09:29 Customer-Centric Investment Strategies
About Karl Dakin
Karl 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.com
About Karen Rands
I'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
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 Takeaways
Sig 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.
Chapters
00:00 Introduction to Compassionate Capitalism
02:56 The Journey of Sig Mosley
05:41 The Role of Angel Investing
08:27 Identifying Coachable Founders
11:35 Understanding Market Competition
14:15 The Importance of Timing in Business
17:17 Success Stories and Lessons Learned
20:05 Reflections on Missed Opportunities
31:21 Navigating Valuation and Relationships in Investments
32:06 Mergers vs. IPOs: Insights from Experience
32:55 The Landscape of Technology Companies in the South
34:49 Cultural Influences on Southern Entrepreneurship
35:45 Empowering Diverse Entrepreneurs in Atlanta
39:31 Winding Down Mosley Ventures and Future Plans
41:09 The SIGI Awards: Celebrating Angel Investors
45:14 Encouraging Angel Investment in the Community
54:12 Final Thoughts on Angel Investing and Community Impact
About Sig Mosley
Sig 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.com
About Erik Nelson
Erik 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.com
About Karen Rands
I'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 Compassionalist Academy : bit.ly/CA-prelaunch
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.
Takeaways
Debt 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 Chapters
00:00 Understanding Access to Capital
02:50 The Role of Debt in Business Growth
05:30 Case Study: Financing Challenges and Solutions
08:16 Job Costing and Profitability
10:20 Improving Business Credit and Financial Health
13:33 Purchase Order Financing Explained
16:16 Navigating Contracts and Agreements
19:07 Risks in Purchase Order Financing
21:42 Insurance and Risk Management in Financing
25:12 Understanding Insurance in Sports and Business
26:13 Navigating SBA Loans for Startups
28:15 The Importance of Debt Service Coverage Ratio
33:37 Challenges with Government Debt and SBA Loans
35:26 The Role of Government Guarantees in SBA Lending
41:57 Franchises vs. Startups: Financing Perspectives
47:32 Creative Financing Strategies for Real Estate
53:50 Building Business Credit for Future Success
About Dominick Wallace
Dominick 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 Rands
I'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
In today’s episode of The Compassionate Capitalist™ Show, I team up with Erik Nelson, President of Coral Capital, Mountain Share Transfer, and Sterling Holdings, for a deep dive into one of the most mission-critical skills for any founder: the investor pitch.
Whether you’re a startup founder preparing for your first angel pitch or a growth-stage CEO aiming to engage an investment banker for a potential IPO, your pitch deck can either open doors, or close them. This is your chance to tell a compelling story that sparks interest, builds trust, and moves investors to act.
Together, Erik and I break down the essentials of a winning investor presentation; what belongs in your deck, how to position your business model, what investors really want to know, and how to avoid the common pitfalls that derail even promising companies.
We also explore the nuances of investor psychology, how to leave room for curiosity (and follow-up questions), and why practice and preparation are non-negotiable. This episode was first recorded for our Capital Conversations series, and I’m excited to now share it with my Compassionate CapitalistTM audience.
This is your playbook for building a pitch that gets remembered and funded, whether you’re raising your first round or refining your pitch for institutional capital.
Key Takeaways
A pitch deck is not a business plan; it's a visual representation of your business.
The goal of an investor presentation is to secure a follow-up meeting, not immediate funding.
Investors want to know how they will make money from your investment.
Understanding your market size is crucial for attracting investors.
Your management team plays a vital role in gaining investor confidence.
Financial models should be dynamic and reflect real business scenarios.
Tailor your presentation to the audience you are addressing.
Leave investors wanting more to encourage follow-up discussions.
Practice your pitch to ensure clarity and confidence.
Be prepared to address uncertainties and have a plan B.
Episode Chapters
00:00 – Unlocking Investor Presentations
02:27 – Common Pitfalls That Undermine a Pitch
06:45 – Why Clarity & Focus Matter More Than Flash
11:51 – The Anatomy of a Winning Pitch Deck
17:51 – Market Size, Trends & Opportunity Framing
21:29 – Financial Models & Key Performance Metrics
29:40 – Why the Management Team Matters So Much
32:32 – Understanding Investor Psychology
34:40 – Building Investor-Ready Financial Narratives
37:37 – Telling the Right Financial Story
40:37 – Tailoring Your Message for Different Investor Types
42:26 – How to Hold Attention & Build Investor Engagement
47:34 – The Feedback Loop: Improving with Every Pitch
55:32 – Handling Objections & Answering the Tough Questions
About Erik Nelson
Erik 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.com
About Karen Rands
I'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 🎓 Join the Academy: bit.ly/CA-prelaunch
In this episode of The Compassionate Capitalist ™ Show, I sit down with Ali Madhavji, an inspiring entrepreneur whose journey from refugee to global blockchain leader is nothing short of remarkable.
We dive into the game-changing potential of blockchain technology and how it’s already transforming industries like finance and healthcare. Ali shares insights from his experience as a venture capitalist and the critical role VCs play in fueling innovation.
We also touch on the powerful intersection of AI and blockchain, and how these technologies together can drive financial inclusion and help lift communities out of poverty. If you're curious about where entrepreneurship and emerging tech are headed, this is a conversation you won’t want to miss.
🎯 After listening to my conversation with Tony Erwin, here are the key takeaways to remember:
Blockchain is transforming industries like finance and healthcare, with the potential to streamline processes and drive innovation.
Venture capital is shifting to support purpose-driven startups, especially those leveraging blockchain and AI to solve real-world problems.
Resilience and passion are essential traits for entrepreneurs navigating the ups and downs of building impactful businesses.
The synergy of AI and blockchain can enhance decision-making and create more efficient, transparent systems.
Financial inclusion remains a global priority, and emerging technologies are key to expanding access and reducing poverty.
Chapters
00:00 Exploring Blockchain Technology
04:15 The Journey of Ali Madhavji
06:55 From Corporate to Venture Capital
09:29 Building a Portfolio of Startups
12:20 The Role of Passion in Investment
15:07 Innovative Solutions in the Pet Industry
25:43 The Intersection of Blockchain and Healthcare
28:31 Innovative Startups and the African Remittance Story
34:44 Blockchain's Role in Financial Inclusion
39:07 AI and Blockchain: A Symbiotic Relationship
43:14 Resilience in Entrepreneurship and Startup Culture
44:39 Crypto Knights: A New Era of Investment Shows
About the Guest – Aly Madhavji Aly Madhavji is the Founding Managing Partner at Blockchain Founders Fund, where he invests in high-impact startups in Blockchain, AI, IoT, and Web3. He also serves as a Limited Partner in other venture funds, mentors entrepreneurs through global incubators; including a leading accelerator in China, and advises international organizations on technology-driven solutions.
Aly works closely with the United Nations on initiatives that leverage FinTech and blockchain to address critical socio-economic challenges. Most recently, he joined the cast of CryptoKnights, the latest innovation and investor reality competition series now streaming on Prime Video, where he evaluates and backs bold new ventures.
To explore Aly’s portfolio or pitch your startup for investment consideration, visit: https://blockchainff.com
About the Host – Karen RandsI’m Karen Rands, and I help entrepreneurs and investors build wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share real conversations and practical strategies to help you grow, fund, and exit your business the smart way.
🔗 Learn more: karenrands.co
🎙 Listen to all episodes: thecompassionatecapitalistshow.com
📘 Download my free ebook: The 4 Ws of Crowdfund Investing
🎓 Join the Compassionalist Academy: bit.ly/CA-prelaunch
In this episode of The Compassionate Capitalist ™ Show, I dive deep into the world of Reg A+ equity crowdfunding, one of the most powerful yet misunderstood tools for democratizing wealth creation. Whether you're a retail investor looking to diversify beyond the stock market or an entrepreneur seeking alternative capital without VC strings attached, this conversation is for you.
I break down the Four W’s of Crowdfunding; Who can invest, What makes Reg A+ different, Where to find promising opportunities, and Why this matters now more than ever. Drawing from my upcoming book and years of experience advocating for economic empowerment, I show how Reg A+ opens the door for everyday people to invest like the wealthy and for founders, especially those often overlooked by traditional finance, to raise significant capital while staying in control.
From transparency in offerings to strategies for vetting deals, you'll walk away with actionable insights to make smarter investment choices or structure a campaign that attracts aligned investors.
💡 Listen through to the end for exclusive access to resources that can help you get started on your crowdfunding journey, whether you're on the founder side or the investor side.
Key Takeaways
Reg A+ gives investors early access to high-growth private companies before they go public.
Lower investment minimums mean more people can participate in wealth-building opportunities.
Transparency in offerings makes it easier to evaluate risk and potential.
Crowdfunding empowers diverse and underrepresented founders.
Reg A+ supports portfolio diversification beyond public markets.
Investors must do their homework—due diligence is non-negotiable.
Entrepreneurs can raise millions without giving up equity control to VCs.
Values-aligned investing offers the potential for profit and purpose.
Episode Chapters
00:00 – Welcome: What Reg A+ Crowdfunding Is & Why It Matters
04:53 – What Investors Need to Know About Reg A+
10:10 – How Entrepreneurs Can Benefit Without Venture Capital
15:55 – Portfolio Strategies Using Reg A+
22:32 – The Power of Transparency & Regulation
28:23 – How to Find & Evaluate Reg A+ Investment Opportunities
33:53 – Marketing Tips for Founders Running a Reg A+ Campaign
39:09 – Wrap-Up: Tools & Resources to Get Started
About Your Host – Karen Rands
I'm Karen Rands, your guide to compassionate capitalism. As a thought leader, investor advocate, and entrepreneur coach, I help visionaries grow and fund their ventures the smart way. Through this show and my Compassionate Capitalist Movement, I’m here to equip you with the tools to build wealth with purpose.
🔗 Learn more: karenrands.co
🎧 Listen to all episodes: thecompassionatecapitalistshow.com
📘 Free eBook: The 4 Ws of Crowdfund Investing
🎓 Join the Academy: bit.ly/CA-prelaunch
How do you know if a startup is a good investment, or a red flag in disguise?
In this episode of The Compassionate Capitalist ™ Show, I share what I look for when reviewing a founder’s pitch deck, business plan, forecasts, and offering documents.
When I led the Network of Business Angels and Investors and produced major venture conferences, I had to vet hundreds of companies. That’s why I created my 10-point checklist and scoring system; Green Light, Yellow Light, Red Light to assess whether a business is truly capital ready.
I’ll walk you through the critical areas investors should evaluate: financial literacy, value proposition, market understanding, and competitive landscape. I also highlight the importance of a strong management team, realistic ROI potential, and avoiding the trap of overvaluation, especially with so-called unicorns.
Whether you're raising capital or reviewing deals, you’ll learn how to steer clear of the "capital abyss" and the dreaded "plateau of death" where returns stall.
Listen to the end for an invitation to my Compassionate Capitalist Audit, a second-opinion review for founders and investors alike.
Here are key takeaways from this episode
Understanding the flow of capital is crucial for entrepreneurs.
Identifying red flags can prevent unnecessary risk for investors.
A well-prepared business plan is essential for attracting capital.
Financials should tell a coherent story about the business.
Target market clarity is vital for effective marketing strategies.
Unique selling propositions must be clearly defined.
Competition analysis is critical for business success.
Traction and KPIs are indicators of a company's potential.
Management teams should have relevant experience and skills.
Investment structures must be well thought out to ensure investor confidence.
Chapters
00:00 Introduction to Capitalist Conversations
06:25 Investor Preparedness and Business Plan Review
18:58 Target Market and Unique Selling Proposition
27:54 Competition and Barriers to Entry
32:51 Understanding Competition and Market Dynamics
45:24 Assessing Management Teams and Advisory Boards
56:36 Navigating Unicorn Valuations and Market Realities
About the Host – Karen Rands
I’m Karen Rands, and I help entrepreneurs and investors build wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share real conversations and practical strategies to help you grow, fund, and exit your business the smart way.
🔗 Learn more: karenrands.co
Listen to all episodes: thecompassionatecapitalistshow.com
📘Download my free ebook: The 4 Ws of Crowdfund Investing
🎓 Join the Compassionalist Academy: bit.ly/CA-prelaunch
In this episode of The Compassionate Capitalist ™ Show, I sit down with blockchain expert Tony Erwin to unpack the real-world ways blockchain is disrupting business and transforming finance. We dive into five powerful use cases, provenance tracking, payment solutions, digital identity, customer engagement, and the tokenization of real-world assets and what they mean for entrepreneurs and investors alike.
We also explore Georgia’s emerging role as a hub for blockchain innovation, thanks to its vibrant fintech community and policy environment that’s beginning to embrace digital assets. Tony shares insights from his work with P2P Cash and explains why educating lawmakers and business leaders about blockchain’s potential is critical for future growth.
If you’ve been curious about how blockchain fits into the future of business, this conversation will give you clarity, and maybe even a little excitement about what’s ahead.
After listening to my conversation with Tony Erwin, here are the key takeaways to remember:
Blockchain is revolutionizing business, with major impacts on efficiency and security.
Provenance and tokenization are transforming industries like food, manufacturing, and finance.
Digital identity and AI are reshaping the future of personal and business security.
Georgia’s thriving fintech ecosystem positions it as a leader in blockchain innovation.
Education and advocacy are essential for driving blockchain adoption and its full potential.
Chapters
00:00 Introduction to Blockchain and Its Impact
05:14 Tony Erwin's Journey into Blockchain
08:52 Blockchain as a Transformational Technology
11:22 Five Ways Blockchain is Changing Business
15:09 Applications of Blockchain in Various Industries
18:18 Tokenization of Real World Assets
21:33 Operational Efficiency through Tokenization
24:28 The Evolution of Blockchain in Finance
29:00 Georgia's Potential as a Blockchain Leader
34:18 Advocacy and Policy in Blockchain Technology
42:07 Innovations in Peer-to-Peer Cash Systems
About the Guest – Tony Erwin
Tony Erwin is a Certified Blockchain Architect and Founder of Skyrocket Financial Solutions, a firm helping businesses unlock the potential of blockchain. He also represents Georgia in the U.S. Blockchain Coalition and is a member of the Global Blockchain Business Council.
Committed to driving innovation, Tony recently launched Future Tech Georgia, a nonprofit focused on advancing blockchain in public policy and economic development across the state.
📘 Explore resources and services at: https://www.skyrocketfinancial.com/
📰 Stay informed and join the conversation: https://futuretechga
About the Host – Karen Rands
I’m Karen Rands, and I help entrepreneurs and investors build wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share real conversations and practical strategies to help you grow, fund, and exit your business the smart way.🔗 Learn more: karenrands.co🎙 Listen to all episodes: thecompassionatecapitalistshow.com📘 Download my free ebook: The 4 Ws of Crowdfund Investing🎓 Join the Compassionalist Academy: bit.ly/CA-prelaunch
In this episode of The Compassionate Capitalist Show, I sit down with Jenny Kassan, a seasoned attorney, author, and president of the Crowdfunding Professional Association to discuss how crowdfunding can be a powerful tool to close the wealth gap and fund businesses without compromisingownership or vision.
Jenny shares her journey from Yale Law School to the front lines of economic justice, advocating for community-based investment models that empower underrepresented entrepreneurs. We unpack the systemic barriers to capital, the widening racial wealth gap, and why traditional financing often leaves small businesses behind.
This episode dives into the practical and strategic side of raising capital, exploring revenue-based financing, the pros and cons of debt vs. equity, and how to align your fundraising strategy with your business model. Whether you're a founder, investor, or policymaker, you'll walk away with powerful insights on how to fund innovation while building stronger local economies.
🎯 After listening to myconversation with Jenny Kassan, here are the key takeaways to remember:
Chapters00:00 Introduction to Wealth Creation and Capital Access02:25 The Role of Crowdfunding in Economic Development05:16 Meet Jenny Kassan: A Champion for Entrepreneurs06:04 Jenny's Journey: From Yale to Public Service08:32 Understanding Economic Disparities and Structural Issues11:30 The Importance of Access to Capital15:21 Crowdfunding as a Path to Economic Mobility18:31 Revenue-Based Financing: A New Approach25:35 Community Impact and Success Stories31:36 Understanding Debt vs. Equity Financing35:22 Designing Your Fundraising Strategy39:04 The Importance of Investor Mindset40:46 Community-Based Finance Success Stories46:00 Building Local Ecosystems for Investment49:37 Advocacy and Future of Crowdfunding
About the Guest – Jenny Kassan
Jenny Kassan is the founder of The Kassan Group, where she offers legal and strategic support for capital raises tailored to small businesses. She’s the author of Raise Capital on Your Own Terms and a nationally recognized leader in impact investing. With nearly 30 years of experience, Jenny now leads the Crowdfunding Professional Association and continues to champion a more inclusive financial future.🌐 Learn more at jennykassan.com📘Check out the Crowdfunding Professional Association: cfpa.org
About the Host – Karen Rands
I’m Karen Rands, and I help entrepreneurs and investors build wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share real conversations and practical strategies to help you grow, fund, and exit your business the smart way.
🔗 Learn more: karenrands.co
🎙 Listen to all episodes: thecompassionatecapitalistshow.com
📘 Download my free ebook: The 4 Ws of Crowdfund Investing
🎓Join the Compassionalist Academy: bit.ly/CA-prelaunch
In this episode, I dive into the core of what Compassionate Capitalism really means and that’s creating wealth for yourself while lifting up entrepreneurs in the process. One of the most powerful tools we have today to make that happen is crowdfunding investing.
I break down the different types of crowdfunding, and why equity crowdfunding is such a game changer, not just for startups, but for everyday investors who want to put their money to work with meaning.
I also tackle the big question: "Is it risky?" Sure, there are risks, but I explain how to navigate them wisely. More importantly, I stress how critical it is that women and minorities get equal access to these wealth-building opportunities.
If you've ever thought about investing in a way that aligns with your values, this episode is your roadmap. Join me as we explore how you can build wealth with purpose through crowdfunding investing.
Key takeaways from the episode:
Compassionate Capitalism means building wealth while making a difference.
Crowdfunding opens access to early-stage investing for everyone.
Equity crowdfunding lets you own a piece of businesses you believe in.
Education reduces risk and leads to smarter investing.
Inclusive investing helps close the wealth gap.
Chapters
00:00 Introduction to Compassionate Capitalism
03:56 The Importance of Funding for Entrepreneurs
06:51 Understanding Crowdfunding Investing
12:45 Types of Crowdfunding Investments
20:20 Risk and Misconceptions in Investing
29:56 Investing in Solutions for Tomorrow
34:29 The Democratization of Investment
39:41 Empowering Underrepresented Investors
47:31 Building Wealth Through Community Investment
54:14 Strategies for Sustainable Wealth Building
About Me: I’m Karen Rands, and I help entrepreneurs and investors create wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share practical advice and real conversations to help you build, scale, and exit businesses the smart way.
📲 Learn more at karenrands.co
See all our podcast episodes at http://thecompassionatecapitalistshow.com
Sign up for Compassionalist Academy https://bit.ly/CA-prelaunch
Download my free ebook “4Ws of Crowdfunding” https://bit.ly/FreeCrowdfundInvestingBook
In this episode of The Compassionate Capitalist Show, I sit down with Dr. Howard Polansky former dentist turned financial coach, to explore how small business owners can escape the cycle of debt and regain control of their finances. Learn how to use lines of credit strategically, reduce interest payments, and improve cash flow without sacrificing growth.
If you're tired of letting your finances control your future, this episode will show you how to become your own CFO - a Cash Flow Optimizer, so you can grow your business and live the life you’ve worked so hard to build.
Key Takeaways:
Many startups rely on personal credit to get off the ground, which can become a long-term burden.
Investors prefer to fund revenue-generating strategies, not debt repayments.
Lines of credit, when cycled properly, can lower interest and reduce monthly payments.
Interest-only payments offer flexibility for businesses needing cash flow.
Not all debt is created equal—know the difference between fixed loans and lines of credit.
Paying extra on your mortgage doesn’t reduce the monthly obligation—learn smarter strategies.
Access to liquidity is crucial for day-to-day operations and long-term growth.
Strategic financial planning can lead to faster business acceleration and reduced stress.
Entrepreneurs need financial education to make informed decisions and take back control.
Becoming your own CFO starts with understanding your numbers and using the right tools.
Chapters
00:00 Introduction to Compassionate Capitalism
04:05 Understanding Startup Debt Challenges
07:52 Dr. Polansky's Personal Journey
12:20 The Shift from Dentistry to Financial Coaching
13:11 Strategies for Managing Debt
18:40 Utilizing Lines of Credit Effectively
23:39 Optimizing Cash Flow for Business Owners
29:57 Understanding Lines of Credit and Debt Management
36:20 The Importance of Interest Rates and Loan Structures
40:34 Final Thoughts and Resources for Business Growth
About Dr. Howard Polansky
Dr. Howard Polansky is a former dentist turned financial strategist who now helps small business owners implement simple systems to dramatically lower fixed debt payments. His approach allows entrepreneurs to reduce financial stress, improve monthly cash flow, and reach their business and lifestyle goals faster.
Grab his free ebook: “Financially LED or Financially Dead? The Introduction to Cash Flow Optimization” 👉 financiallyled.com/ebook
About the Karen Rands
I’m Karen Rands, host of The Compassionate Capitalist Show and advocate for innovation-led wealth creation. My mission is to help entrepreneurs and investors scale businesses strategically and profitably—with the right capital and smart planning.
Learn more: karenrands.co Full podcast archive: The Compassionate Capitalist Show Join the Compassionate Capitalist Academy: Sign Up Here Download my free eBook: “12 Secrets of Innovation and Wealth”
In this episode, I sit down with communication expert Alfred Poor to talk about a skill every entrepreneur needs but only few truly master - how to show up and stand out on video. Whether you are pitching to investors, leading a virtual team or presenting at a conference, your presence on screen can make or break your message.
We talk about the practical stuff like posture, eye contact, and why those fancy virtual backgrounds might be hurting more than helping. We talk about the importance of being intentional in how you communicate, how to ease presentation jitter and why strong openings and closings are key to leaving a lasting impression.
If you are a founder or visionary leader, this conversation will give you the tools to connect with your audience, build credibility and guide them towards that all-important next step in your business journey.
After listening to my conversation with Alfred Poor on this episode of The Compassionate Capitalist Show, here are six key lessons I want you to take to heart when showing up on video:
Chapters
00:00 The Importance of Video Communication for Founders
06:53 Introducing Alfred Poor: The Video Meeting Advisor
13:43 Key Strategies for Effective Virtual Presentations
19:34 Enhancing Engagement Through Nonverbal Communication
24:41 Practical Tips for Setting Up Your Video Environment
24:59 The Importance of Posture and Presence
26:45 Navigating Virtual Backgrounds Effectively
31:55 Mastering In-Person Presentations
33:08 Overcoming Presentation Anxiety
35:59 The Art of Engaging Presentations
38:33 Crafting a Strong Start and Finish
41:32 The Goal of Engagement in Pitches
About the Guest - Alfred Poor
Alfred Poor is a keynote speaker, tech expert, and trusted video meeting advisor. He helps leaders and founders show up with confidence and clarity in virtual presentations, so their message truly lands. As a mentor with the Founder Institute and founder of The 75% Solution, Alfred empowers startups around the world to pitch with impact on screen.
Learn more at 👉 the75percent.com
About Me:
I’m Karen Rands, and I help entrepreneurs and investors create wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share practical advice and real conversations to help you build, scale, and exit businesses the smart way.
📲 Learn more at karenrands.co
If you've ever thought about selling your business or investing in one that might be sold down the road, this episode is for you.
In this episode of The Compassionate Capitalist Show, I sit down with Rob Levin, Managing Partner at CIS Ventures, to talk about what it really takes to prepare your business for a successful and profitable exit.
Rob brings a wealth of experience from his time at Ernst & Young, his years as a serial entrepreneur, and now as an M&A advisor helping business owners avoid the common pitfalls that tank deals or leave money on the table.
What I love about Rob's approach is how focused he is on intentionality. He doesn’t just help businesses get sold—he helps them get ready to be sold the right way, to the right buyer, for the best possible outcome.
We dig into so much during this conversation, from setting expectations with buyers, to keeping your top talent through a transition, to organizing your books and systems so you’re not scrambling at the last minute. Rob also shares why some companies get premium valuations while others struggle just to close a deal.
💡 Whether you're looking to sell in 12 months or just want to build long-term value, this episode is packed with actionable insights you won’t want to miss.
🎯 What You'll Learn:
⏱️ Chapter Highlights:
00:00 – Intro & Rob’s path from CPA to entrepreneur to M&A advisor
06:18 – Why most deals fail: misalignment & poor preparation
14:11 – The power of intentional planning before you sell
23:35 – Communication during change: don’t lose your top people
29:06 – Preparing your business like a buyer is watching
41:34 – Final advice: act like you’re for sale every day
👤 About My Guest:
Rob Levin is Managing Partner at CISVentures, where he helps founder-led companies prepare for and execute successful exits. His firm provides pre-sale planning, deal structuring, and strategic advisory services to help owners maximize value and avoid costly mistakes.
🎁 Grab Rob’s free Pre-Sale Planning Guide at cisventures.net
👩💼 About Me:
I’m Karen Rands, and I help entrepreneurs and investors create wealth through innovation and capital formation. Through this show and my Compassionate Capitalist Movement, I share practical advice and real conversations to help you build, scale, and exit businesses the smart way.
📲Learn more at karenrands.co
True innovation often begins decades before commercialization—sparked by bold Compassionate Capitalists funding risky ideas to solve global challenges.
In this episode of The Compassionate Capitalist Show, Karen Rands sits down with Melissa Beck, President of Anonymous Philanthropy, to reveal how strategic giving, grounded in entrepreneurial principles, can drive breakthroughs—from AI to virtual reality to space exploration.
Melissa is leading the charge to transform the coming Great Wealth Transfer into a Great Giving Transfer—inspiring individuals, families, and corporations to use their inherited or earned wealth with strategy and measurable impact.
We’ll explore why investing in communities, building sustainable wealth, and solving systemic issues are not only moral imperatives but also smart, scalable strategies for lasting change. Melissa’s journey—from Silicon Valley to nonprofit leadership to managing billion-dollar philanthropic portfolios—provides a powerful roadmap for making money matter.
This is a must-listen for anyone ready to embrace compassionate capitalism and fuel a better future.
🎯 Key Takeaways:
🔗 Learn more about the Ansari XPRIZE’s impact on innovation:
Visit XPRIZE History
🎬 Chapters:
00:00 – The Essence of Compassionate Capitalism
04:36 – Transforming Wealth into Philanthropy
11:38 – Innovating Nonprofits for Greater Impact
20:44 – Shifting the Philanthropic Paradigm
27:53 – Leveraging Prizes for Innovation
31:30 – Challenges in Philanthropic Outcomes
37:41 – Teaching Investment in Communities for Sustainable Wealth
📚 About the Guest:
Melissa Beck is President of Anonymous Philanthropy, an advisory firm helping individuals, families, foundations, and corporations maximize the impact of their charitable dollars. Representing billions in philanthropy, Melissa’s team brings strategic, measurable outcomes to what is often an emotional giving process.
Previously, Melissa served as CEO of Big Brothers Big Sisters of Orange County, where she led 300% revenue growth, achieved single-digit turnover, and earned national honors—including being the first nonprofit executive recognized at the Ernst & Young Entrepreneur of the Year Awards.
Learn more: www.anonymousllc.com
🎧 Listen Now:
Catch the livestream replay on LinkedIn, YouTube, or stream it on Spotify and all major podcast platforms next week.
💬 Got a question for Karen or Melissa?
Email: karen@kugarandholdings.comor info@anonymousllc.com
Subject Line: Podcast Question – Transforming Wealth to Impact
What if your most passionate customers could also be your investors?
That question sparked an entire movement—and helped reshape the future of early-stage finance. In this episode of The Compassionate Capitalist Show, I sit down with one of the original architects of the investment crowdfunding revolution, Sherwood “Woodie” Neiss.
Woodie is the Principal at Crowdfund Capital Advisors and the co-founder of the regulated investment crowdfunding movement. He literally walked the halls of Congress to help pass the JOBS Act, giving everyday people the right to invest in startups and private companies—an asset class that had been historically restricted to the wealthy.
He’s also behind a suite of groundbreaking platforms:
Now, Woodie is back with a powerful new book: Investomers: How Customers-Turned-Investors Are Shaping the Future of Early-Stage Finance. In this fast-moving conversation, we dig into how this shift is transforming fundraising, why data is driving the future of private investing, and how startups can build resilient communities of investor-supporters.
This is a deep dive into the history, impact, and next wave of economic democratization; you don’t want to miss it
🎯 Key Takeaways:
🎬 Chapters
00:00 Introduction to Crowdfunding and Economic Democratization
06:37 Woody Neiss: A Pioneer in Crowdfunding
11:53 The Journey of FlavorX and Its Impact
18:46 Advocating for Change: The Crowdfunding Legislation
24:34 The Importance of Data in Crowdfunding
29:37 Building a Comprehensive Crowdfunding Database
30:45 Navigating Secondary Trading and Compliance
33:03 Building a Technology Platform for Secondary Trading
34:47 Insights and Reports: Understanding the Crowdfunding Landscape
36:59 Offering Insight Reports: Valuation and Industry Comparisons
38:15 Capital Pulse: Analyzing Investment Signals
40:27 Launching a Venture Fund: Investing in Early Stage Companies
44:14 The Future of Investment Crowdfunding
49:10 The State of Venture Capital and Crowdfunding Awareness
54:33 The Rise of Influencers in Investment Crowdfunding
🎧 Listen Now:
Listen now and find out how to turn your customers to investors.
📌 Learn more about Karen Rands' work with entrepreneurs: Entrepreneurial Services📌See the businesses Karen has helped: Customer Projects📌Book a consultation with Karen: Schedule a Quick Call
🚀 Like this episode? Follow, share, and drop a comment—let’s spread the word on converting customers to investors.
💬 Got a question for Karen or Woodie? Email: karen@kugarandholdings.comor sherwood@theccagroup.com
What Happens After a 9-Figure Exit? You Keep Building. 💼💥
When you’ve exited a company for nine figures—what’s next? For Jon Gosier, the answer was simple: build again, smarter and bigger.
In this episode of The Compassionate Capitalist Show, I reconnect with Jon Gosier, a serial entrepreneur who’s redefining what it means to create wealth across industries. From his time bootstrapping tech startups in Africa to co-founding Audigent—the adtech company that sold to Experian in late 2024—Jon has always been ahead of the curve. Now, with FilmHedge, he's bringing the same innovation to film financing, using fintech and AI to modernize how entertainment projects get funded.
Whether you’re a founder, investor, or creative, this conversation will shift how you think about exits, partnerships, and funding the future.
💡 What You’ll Learn in This Episode:
✔️ The untold story behind Audigent’s 9-figure acquisition by Experian
✔️ Why Jon walked away from adtech to pursue innovation in film and fintech
✔️ How FilmHedge is using AI and data to transform Hollywood finance
✔️ The challenges of bootstrapping and co-founder dynamics
✔️ What to consider when weighing IPO vs acquisition
✔️ How entrepreneurs can create long-term impact across multiple industries
🧭 Chapters
00:00 – Introduction to Jon Gosier's Journey
01:58 – The Vision Behind Audigent
06:41 – Understanding the AdTech Ecosystem
10:44 – Experian's Acquisition and Data Insights
12:22 – Transitioning to FilmHedge
14:51 – The Evolution of Entrepreneurial Vision
20:12 – Bootstrapping and Fundraising Challenges
22:48 – Exploring Exit Strategies
25:50 – FilmHedge: A FinTech Approach to Film Financing
29:50 – Understanding Film Financing and Distribution
36:10 – The Role of Southbox Entertainment
44:11 – Navigating the Application Process
49:00 – Building a Thriving Film Ecosystem
📌 Learn more about FilmHedge: filmhedge.com/criteria
📌 Watch Jon’s TED Talk: The Problem with Trickle-down Techonomics
📌 Explore Southbox Entertainment’s model
🎙️ About Karen Rands:
Karen Rands has spent 20+ years helping entrepreneurs and investors navigate capital strategy and business growth.
📌 Schedule a Quick Call
📌 Explore Entrepreneurial Services
📌 See Past Projects
🚀 Like this episode? Follow, share, and leave a comment to help us spread powerful wealth-building strategies for today’s entrepreneurs and investors.
#AdTech #Fintech #FilmFinance #Entrepreneurship #StartupExit #DataDrivenInvesting #FounderJourney #CompassionateCapitalist
As a founder, you’re always communicating—whether you’re hiring, pitching to investors, or navigating tough conversations with employees or the media. But are you using interview skills to your advantage?
In this episode of The Compassionate Capitalist Show, I sit down with Kim Chandler McDonald, an award-winning author, storyteller, and the Co-Founder & CEO of 3 Steps Data and FlatWorld Integration. Kim has spent her career helping leaders master communication while also driving innovation in data security, governance, and compliance.
We dive into insights from her latest book, An Interviewer’s Guidebook: Turning Conversations into Captivating Stories, and explore how founders can leverage interview techniques to strengthen their business relationships, refine their messaging, and communicate with confidence.
🔹 Key Takeaways:
✔️ How to conduct interviews that inspire, inform, and persuade
✔️ The biggest mistakes founders make when hiring—and how to fix them
✔️ How technical founders can simplify complex ideas for investors and customers
✔️ Strategies for handling high-stakes conversations with investors, employees, and the media
✔️ Best practices for data governance and security in today’s digital world
🔑 Why This Matters: Mastering the art of asking the right questions and telling compelling stories can set you apart in business. Whether you’re building a team, pitching your startup, or negotiating deals, strong communication skills can be your greatest asset.
🎧 Listen Now & Elevate Your Communication Game!
📌 Learn more about Kim Chandler McDonald: 3 Steps Data
📌 Get free resources from her book: Interview Guidebook Resource Hub
📌 Book a call with Kim: Connect Here
📌 Learn more about Karen Rands' work with entrepreneurs: Entrepreneurial Services
📌 See the businesses Karen has helped: Customer Projects
📌 Book a consultation with Karen: Schedule a Quick Call
🚀 Like this episode? Follow, share, and drop a comment—let’s spread the word on mastering communication for business success!
#Entrepreneurship #Communication #InterviewSkills #InvestorRelations #Leadership #CompassionateCapitalist #BusinessGrowth
The Hidden Financial Leaks That Could Sink Your Business.
Cash flow is king. But mismanaged cash flow? That’s a silent killer.
Too many businesses—especially in high-growth industries like construction and manufacturing—are profitable on paper but bleeding cash in reality. The reason? Poor financial structure, lack of strategic budgeting, and failing to track hidden costs.
Today on The Compassionate Capitalist Show, I sit down with Luke Boyenger, CEO of Cruzumi CFO & Advisory—a firm dedicated to helping contractors and construction companies maximize profits and take control of their finances.
✔️ How to fix your cash flow leaks before they sink your business
✔️ The critical difference between a CFO, Controller, and VP of Finance (because not all CFOs are created equal)
✔️ Why “profit” doesn’t mean you can take out cash—and how high-growth businesses should actually fund expansion
✔️ The hidden financial mistakes that put construction companies out of business (Luke literally wrote the book on this!)
✔️ Why smart founders leverage Fractional CFOs instead of hiring full-time finance teams
👷♂️ Construction & Contracting CEOs struggling with unpredictable cash flow
💼 Entrepreneurs in capital-intensive businesses navigating growth challenges
📈 Angel Investors & VCs looking to ensure their portfolio companies aren’t making fatal financial missteps
If financial clarity, strategic budgeting, and wealth creation matter to you, this episode is a must-listen. 🎧
🔗 Listen now & subscribe → https://open.spotify.com/episode/6MuRer695BA0FMV8tlozOI 📖 Get Luke’s book: “7 Financial Mistakes That Put Construction Companies Out of Business” → https://www.cruzumicfo.com/7mistakes
🌎 Learn more about Cruzumi CFO & Advisory → http://cruzumi.com
#CFO #FractionalCFO #CashFlow #CashFlowManagement #Profit #ConstructionIndustry #FinancialClarity #WealthCreation
Struggling to scale your business? Need growth capital but hitting roadblocks with banks, angels, or VCs? You’re not alone. Many entrepreneurs reach a plateau—not because of lack of effort, but because they’re missing the hidden growth metrics that drive real, scalable expansion.
📣 That’s why in this episode of The Compassionate Capitalist Show, I sit down with Jason Bryll, Founder of Parable Associates, a business intelligence expert who has helped 1,700+ healthcare providers turn complex challenges into revenue opportunities. And here’s the kicker—his data-driven strategies work across any industry where growth depends on smart decision-making.
🔹 What You’ll Learn in This Episode:
✔️ How to move beyond intuition and build systems for predictable business growth
✔️ Why most CEOs & CFOs miss key performance indicators that can unlock massive revenue
✔️ How data analytics can scale your business from local to national
✔️ What investors (especially private equity) look for in a growth-ready business
✔️ The #1 mistake businesses make when trying to expand—and how to fix it
💡 Why This Matters:
Too many business owners rely on gut feeling instead of data-driven decision-making. Whether you're a founder, an investor, or an ops leader, understanding your business’s hidden metrics can mean the difference between stagnation and explosive growth.
💬 Don’t just guess—get the inside secrets to scaling smarter. Listen now, take action, and drop a comment with your biggest takeaway!
🎧 LISTEN NOW & SCALE YOUR BUSINESS SMARTER!
📌 Learn more about Jason Bryll & Parable Associates → Visit Here
📌 Follow Karen Rands for more growth strategies → Connect Here
📌 Like, Share & Tag an entrepreneur who needs to hear this!
#ScalingBusiness #RevenueGrowth #BusinessIntelligence #DataAnalytics #PrivateEquity #Entrepreneurship #PredictableGrowth
Practice Management & Revenue Cycle Solutions I Parable
Elevate your healthcare practice with our Practice Management & Revenue Cycle solutions. Contact Parable Associates today!
Are you a founder experiencing feelings of stagnation, overwhelm, or difficulty in growing your business?
Are you an angel investor that is frustrated by your portfolio companies not reaching their milestones and growing.
Well then this episode is for you.
In this episode of the Compassionate Capitalist Show, Karen Rands discusses the challenges faced by entrepreneurs and investors in growing businesses. She introduces a five-pillar system designed to help businesses identify growth drivers and reduce chaos. The conversation emphasizes the importance of clarity in vision, building cohesive teams, understanding corporate culture, and the necessity of having a solid business plan. Stuart Webb, a guest with extensive experience in business growth, shares insights on how to navigate growth stages, identify true competition, and the significance of customer feedback in driving innovation.
Stuart Webb brings 30 years of experience in science, research and business. His company, The Complete Approach, builds upon his experience to coach and mentor business owners to grow profits and manage their teams to scale and grow the business value to prepare for exit. To Learn More and Get his Free Resources, visit: http://systemise.me
http://Thecompleteapproach.co.uk
Takeaways
Entrepreneurs often feel overwhelmed and stuck in their growth.
A solid business plan is essential for communicating with investors.
Clarity of vision is the first step in business growth.
Building a cohesive team is crucial for scaling a business.
Corporate culture is defined by behaviors, not just attitudes.
Feedback from customers can lead to new product opportunities.
Investors look for clarity in the business model and customer understanding.
Delegation is key to freeing up time for founders.
Understanding true competition involves knowing your customers' needs.
Collaboration with competitors can lead to win-win situations.
Karen Rands has been advising startups and growth stage companies for over 20 years on where to get the money, the capital they need to launch and grow. She works with owners to align their financing strategy with the business strategy. To schedule a quick call or schedule a consultation session, visit http://bit.ly/KYRintro To learn more about our work with entrepreneurs visit: https://karenrands.co/entrepreneurial-services/ To read about the projects and businesses we have helped: https://karenrands.co/customer-projects/
Please like this episode, follow or subscribe to The Compassionate Capitalist Show. Share with someone or on your social media when you like the content. Thanks – it really helps us grow awareness about this podcast and the valuable content
Chapters
00:00 Introduction to Overcoming Business Growth Challenges
03:48 The Importance of a Business Plan
05:02 Stuart Webb's Journey from Science to Business
12:09 The Five Pillars of Business Growth
14:38 The Challenge of Working In vs. On Your Business
16:19 Effective Delegation and Team Cohesion
22:53 Understanding Corporate Culture
26:46 The Importance of Business Planning
30:46 Clarity in Vision and Customer Understanding
36:44 Identifying True Competition
42:25 Collaboration Over Competition
43:17 Introduction to Compassionate Capitalism
44:26 The Role of Cougarand Capital in Investment Success
Keywords
Compassionate Capitalism, Business Growth, Angel Investing, Corporate Culture, Business Plans, Team Building, Entrepreneurial Strategies, Investor Relations, Market Competition, Wealth Creation
