What Actually Breaks Small Businesses (And How to Avoid It), with Shaun Hayes Entrepreneur, Best Selling Author, Speaker
Tue Jan 13 2026
Shaun Hayes returns for his second appearance to share hard-earned lessons from a career that spans entrepreneurship, banking, and executive leadership. He’s an author and speaker who has built and scaled businesses, evaluated thousands of business plans, and brings a pragmatic operator’s lens to what actually makes companies succeed or fail. This conversation frames his newest book, The Green Choice, as a “gut-check roadmap” for newly minted and aspiring entrepreneurs who want real-world perspective rather than motivational slogans.
Across the episode, Shaun and Raj unpack the realities founders face when leaving “the mothership” of corporate structure: execution over planning, the infrastructure “step function” that forces constant reinvestment, and why cash flow (not just profitability) is the true survival metric in years 1–3. Shaun highlights common failure points—especially leases, poor financing structure, misunderstanding cash cycles, and underestimating the psychology of managing people. He also emphasizes the importance of mentorship, disciplined frugality early on, realistic expectations of team motivation, and the need to build a results-oriented culture. The conversation closes with actionable personal rules: do the tasks you avoid before 9 a.m., and do one uncomfortable thing every day.
Connect with the Host
Twitter: twitter.com/ItsRajTut
LinkedIn: https://www.linkedin.com/in/rajtut/
Instagram: instagram.com/ItsRajTut
TikTok: https://www.tiktok.com/@itsrajtut
Connect with the Guest
LinkedIn: https://www.linkedin.com/in/shaun-hayes-7a613813/
Timestamps
00;00;12 Why founders misjudge how badly others want to win
05;27;52 Why most businesses fail because of leases
09;07;13 How Shaun can read a business by its margins and rent ratios
14;12;56 Why business plans collapse the moment reality hits
18;10;05 The infrastructure “step” problem when scaling
24;31;44 The hard truth: not everyone wants success like you do
28;13;14 Why cash flow matters more than profit
34;14;44 The mindset shift from hourly pay to long-term payoff
43;09;49 Location traps and how bad real estate decisions kill growth
59;17;55 Two rules for success: before 9 a.m. and daily discomfort
#Entrepreneurship #SmallBusiness #BusinessStrategy #CashFlow #Leadership #Management #Scaling #Startups #Mentorship #Sales #PricingStrategy #RealEstateInvesting #Multifamily #PropertyManagement #Operations #FounderMindset #BusinessSystems #RiskManagement #BusinessFinance #Leasing
This podcast is brought to you by Storyboard Living.
If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email deals@storyboardliving.com
Connect with us at our Website: https://storyboardliving.com/
LinkedIn profile: https://www.linkedin.com/company/storyboard-living/
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Shaun Hayes returns for his second appearance to share hard-earned lessons from a career that spans entrepreneurship, banking, and executive leadership. He’s an author and speaker who has built and scaled businesses, evaluated thousands of business plans, and brings a pragmatic operator’s lens to what actually makes companies succeed or fail. This conversation frames his newest book, The Green Choice, as a “gut-check roadmap” for newly minted and aspiring entrepreneurs who want real-world perspective rather than motivational slogans. Across the episode, Shaun and Raj unpack the realities founders face when leaving “the mothership” of corporate structure: execution over planning, the infrastructure “step function” that forces constant reinvestment, and why cash flow (not just profitability) is the true survival metric in years 1–3. Shaun highlights common failure points—especially leases, poor financing structure, misunderstanding cash cycles, and underestimating the psychology of managing people. He also emphasizes the importance of mentorship, disciplined frugality early on, realistic expectations of team motivation, and the need to build a results-oriented culture. The conversation closes with actionable personal rules: do the tasks you avoid before 9 a.m., and do one uncomfortable thing every day. Connect with the Host Twitter: twitter.com/ItsRajTut LinkedIn: https://www.linkedin.com/in/rajtut/ Instagram: instagram.com/ItsRajTut TikTok: https://www.tiktok.com/@itsrajtut Connect with the Guest LinkedIn: https://www.linkedin.com/in/shaun-hayes-7a613813/ Timestamps 00;00;12 Why founders misjudge how badly others want to win 05;27;52 Why most businesses fail because of leases 09;07;13 How Shaun can read a business by its margins and rent ratios 14;12;56 Why business plans collapse the moment reality hits 18;10;05 The infrastructure “step” problem when scaling 24;31;44 The hard truth: not everyone wants success like you do 28;13;14 Why cash flow matters more than profit 34;14;44 The mindset shift from hourly pay to long-term payoff 43;09;49 Location traps and how bad real estate decisions kill growth 59;17;55 Two rules for success: before 9 a.m. and daily discomfort #Entrepreneurship #SmallBusiness #BusinessStrategy #CashFlow #Leadership #Management #Scaling #Startups #Mentorship #Sales #PricingStrategy #RealEstateInvesting #Multifamily #PropertyManagement #Operations #FounderMindset #BusinessSystems #RiskManagement #BusinessFinance #Leasing This podcast is brought to you by Storyboard Living. If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email deals@storyboardliving.com Connect with us at our Website: https://storyboardliving.com/ LinkedIn profile: https://www.linkedin.com/company/storyboard-living/