Episode #65 - Thaddeus Voss Owner of Bluegrass Lending
Fri Dec 26 2025
Follow Us On IG: https://www.instagram.com/htbs__?igsh=cTF4N2lpamIycDJ5Follow Thad On IG: https://www.instagram.com/thaddeus_voss_?igsh=MXY3N3luYW92djBneA==In Episode 65 of the How to Business Show, we sit down with Thad Voss, founder of Bluegrass Lending and Lionheart Funding, to pull back the curtain on the alternative funding and creative finance industry. From taking a commission-only Wall Street job in New York with no safety net, to building a multi–eight-figure alternative lending operation, Thad breaks down the realities of merchant cash advances, SBA loans, term loans, unsecured lending, and private money—including the biggest misconceptions business owners have about rates, risk, and regulation.This episode is a masterclass for entrepreneurs, sales professionals, and business owners who want to understand:Why banks fail small businessesHow alternative funding actually worksThe truth about high interest rates and riskHow ethical brokers build long-term client relationshipsWhy most bad actors fail in this spaceHow to scale a brokerage, fund deals in-house, and build real wealthWe also dive deep into:Sales psychology & cold callingBuilding an “undeniable stack of proof” (inspired by Alex Hormozi)Ego, leadership, mentorship, and compounding wealthThe future of alternative lending, regulation, and educationIf you’re a small business owner, real estate investor, sales rep, or someone curious about creative finance and alternative lending, this episode will change how you think about money.Subscribe for more real conversations about business, money, and growth.00:00 – Biggest misconceptions about the alternative funding space02:25 – Why Thad chose Wall Street over a “safe” salaried job04:12 – Moving to New York broke, scared, and commission-only08:05 – The brutal reality of early sales & clawback periods10:35 – The internship play that changed everything13:42 – What alternative funding really is (creative finance explained)17:09 – Merchant cash advances vs SBA loans vs term loans26:01 – Bad actors, unethical brokers, and industry misinformation34:24 – Why high rates exist (and why businesses still take them)39:18 – Bluegrass vs Lionheart: brokerage vs in-house funding46:52 – Ego, wealth, syndication, and compounding returns56:26 – Books that shaped Thad’s mindset (10X, Fanatical Prospecting, Ego Is the Enemy)1:02:26 – Walk-up song for business meetings 🎶
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Follow Us On IG: https://www.instagram.com/htbs__?igsh=cTF4N2lpamIycDJ5Follow Thad On IG: https://www.instagram.com/thaddeus_voss_?igsh=MXY3N3luYW92djBneA==In Episode 65 of the How to Business Show, we sit down with Thad Voss, founder of Bluegrass Lending and Lionheart Funding, to pull back the curtain on the alternative funding and creative finance industry. From taking a commission-only Wall Street job in New York with no safety net, to building a multi–eight-figure alternative lending operation, Thad breaks down the realities of merchant cash advances, SBA loans, term loans, unsecured lending, and private money—including the biggest misconceptions business owners have about rates, risk, and regulation.This episode is a masterclass for entrepreneurs, sales professionals, and business owners who want to understand:Why banks fail small businessesHow alternative funding actually worksThe truth about high interest rates and riskHow ethical brokers build long-term client relationshipsWhy most bad actors fail in this spaceHow to scale a brokerage, fund deals in-house, and build real wealthWe also dive deep into:Sales psychology & cold callingBuilding an “undeniable stack of proof” (inspired by Alex Hormozi)Ego, leadership, mentorship, and compounding wealthThe future of alternative lending, regulation, and educationIf you’re a small business owner, real estate investor, sales rep, or someone curious about creative finance and alternative lending, this episode will change how you think about money.Subscribe for more real conversations about business, money, and growth.00:00 – Biggest misconceptions about the alternative funding space02:25 – Why Thad chose Wall Street over a “safe” salaried job04:12 – Moving to New York broke, scared, and commission-only08:05 – The brutal reality of early sales & clawback periods10:35 – The internship play that changed everything13:42 – What alternative funding really is (creative finance explained)17:09 – Merchant cash advances vs SBA loans vs term loans26:01 – Bad actors, unethical brokers, and industry misinformation34:24 – Why high rates exist (and why businesses still take them)39:18 – Bluegrass vs Lionheart: brokerage vs in-house funding46:52 – Ego, wealth, syndication, and compounding returns56:26 – Books that shaped Thad’s mindset (10X, Fanatical Prospecting, Ego Is the Enemy)1:02:26 – Walk-up song for business meetings 🎶