What Actually Breaks Small Businesses (And How to Avoid It), with Shaun Hayes Entrepreneur, Best Selling Author, Speaker

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

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