Most startups don’t fail from bad ideas. They fail from burnout, bad hiring, and costly blind spots. In this episode, Andrew Ackerman breaks down what actually kills early companies, how founders should think about money and runway, and when to push through versus walk away before the business consumes your life.

Key Takeaways

• Why early startup years are designed to be intense, and why expecting balance too soon backfires
• When buying back your time actually makes sense, and how delegation protects focus
• How perfectionism slows momentum and delays real market feedback
• Which mistakes are survivable, and which ones quietly kill a business
• How the pre-mortem method helps founders test decisions before committing

About Andrew Ackerman
Andrew is a serial entrepreneur, early-stage investor, and startup mentor with two decades of experience building and backing companies. He’s founded multiple startups, invested in over 70 companies, and mentored hundreds of founders through accelerators and venture platforms. Andrew is the author of The Entrepreneur’s Odyssey and brings a practical, hard-earned perspective on building businesses without burning out.


Connect to Andrew

• Website: Andrew Ackerman 
• LinkedIn: Andrew Ackerman | LinkedIn 
• Instagram: @andrewbackerman
• X: @andrewackerman
• Book: The Entrepreneur's Odyssey| Kindle, Paperback, and Hardcover
• 
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Scaling fails when everything depends on the founder. Josh Ax shares how he built teams, systems, and cash-flow-driven businesses that work without constant oversight. This episode dives into delegation, hiring decisions, and why execution beats perfection when you’re building for freedom, not ego. 

Key Takeaways

• Why speed of execution matters more than perfect planning when building a business
• How real estate becomes a long-term wealth vehicle when paired with systems and cash flow discipline
• When to hire, what roles to delegate first, and how to avoid becoming the bottleneck
• How to build teams that own their roles instead of needing micromanagement
• What sustainable growth looks like beyond revenue and deal volume
  
  

About Josh Ax 
Joshua Ax is the CEO and owner of NEPA Cash Offer LLC. He got into real estate in 2014, working in property management. He recognized the value of quick communication and follow-through on commitments while helping the company he worked for grow. In 2016, he and his wife, Lauren, moved to Kingston, PA, so she could attend King’s College. Josh branched off on his own and started his first real estate investment company in 2017, and quickly let go of his real estate license. He has since flipped over 200 properties and is always looking to help the next seller who needs tailored real estate solutions.

Connect to Josh

• Website: NEPA Property Buyers | NEPA Cash Offer 
• LinkedIn: Joshua Ax 

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Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm.

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YouTube: Melanie Sikma 

Burnout isn’t a failure. It’s feedback. Kaci Janson shares how hitting her breaking point forced her to redesign her life, not just her business. This conversation explores why hustle eventually stops working, how better systems create real freedom, and what success looks like when time, family, and presence come first. Listen if you’re done surviving and ready to build something that actually lasts.

Key Takeaways

• Why burnout is often the cost of building a business without designing your life first
• How simplifying to one core focus can unlock more profit and peace than adding more opportunities
• What turns entrepreneurship into freedom, instead of a higher-paid job you can’t escape
• When working in seasons, it creates momentum instead of chasing a balance that never arrives
• Where success quietly shifts once time, health, and family stop being the trade-offs

About Kaci Janson
Kaci Janson is a real estate investor, entrepreneur, and President of FosterED Connection, where she advocates for and supports youth in the foster care system through education and connection. As a single mom, Kaci built a real estate portfolio of over 200 doors using creative financing strategies, demonstrating how unconventional approaches can create significant opportunity and financial independence. She is also the owner of A Boy and His Dog Inc., where she focuses on acquiring and managing real estate assets. Kaci is passionate about helping others, especially women and single parents, understand creative financing, build wealth through real estate, and create stability for their families and communities.

Connect to Kaci

• Website: FosterED Connection
• Instagram: @kacijanson 

Connect with Us 

Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm.

Resources

Curious how much you could be saving? Try the Tax Savings Self-Assessment tool here: https://shorturl.at/4RIc0. 

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YouTube: Melanie Sikma 

Many entrepreneurs don’t fail; they burn out. They build businesses that demand more time, attention, and presence than they can give. In this episode, Jason Seward shares how he left a secure career to build a growing real estate business without sacrificing family, health, or peace. If your business feels like it’s running you, this conversation will help you reset what “success” really means. Press play and choose one change you’ll make this week.

Key Takeaways

• How building a business around your life, not your ego, changes every decision you make
• Why control over your time matters more than revenue growth alone
• What “zooming out” actually looks like when you feel buried in the grind
• How clear lanes and partnerships reduce mental load and decision fatigue
• Why protecting family time requires systems, not willpower

Resources / Links Mentioned

• Scaling Up by  Verne Harnish | Kindle, Paperback, and Hardcover
• Skylight Calendar
• Legacy Family – Mastermind 
  
  

About Jason Seward
Jason is the Founder and Managing Partner of 608B Capital, a real estate debt fund providing short-term lending for fix-and-flip and buy-and-hold investors. After 17 years in insurance sales and leadership, Jason transitioned into real estate full-time in 2022. He is also the host of the Burning The Ships Podcast and is deeply focused on building businesses that support family, freedom, and long-term fulfillment.

Connect with Jason

• Website: 608B Capital
• LinkedIn: Jason Seward 
• Podcast: Burning The Ships 

Connect with Us 

Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm

Resources

Curious how much you could be saving? Try the Tax Savings Self-Assessment tool here: https://shorturl.at/4RIc0. 

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• YouTube: Melanie Sikma 

High income does not automatically create freedom. Many entrepreneurs build impressive net worths while remaining tied to their businesses. In this conversation, Chris Miles explains why cash flow matters more than accumulation and how rethinking money changes what freedom actually looks like.

Key Takeaways

• Why high income often creates a bigger rat race instead of freedom
• How cash flow beats net worth when it comes to real financial security
• What “work optional” actually means and why it’s more achievable than you think
• The hidden danger of locking money inside equity, retirement accounts, or businesses
• How stewardship, not saving or spending, creates long-term abundance
  
  
  

Resources / Links Mentioned

• Profit First by Mike Michalowicz | Kindle, Audio Book, and Hardcover
• The 4-Hour Workweek by Timothy Ferriss | Kindle, Audio Book, and Hardcover
  
  
  

About Chris Miles
Chris is a cash flow strategist and the founder of Money Ripples. Known as the “anti–financial advisor,” he helps entrepreneurs and high-income earners shift from net-worth chasing to cash-flow creation. After retiring twice, losing everything, and rebuilding, Chris now teaches clients how to free up money, fix cash leaks, and build passive income so work becomes optional.

Connect with Chris

• Website: Money Ripples 
• Podcast: Money Ripples Podcast 
• LinkedIn: Chris Miles
• Book: The Work Optional Blueprint | Paperback
  
  
  

Connect with Us 

Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm.

Resources

Curious how much you could be saving? Try the Tax Savings Self-Assessment tool here: https://shorturl.at/4RIc0. 

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YouTube: Melanie Sikma 

Being busy doesn’t mean you’re building the right life. Dan Rivers shares how spreading himself thin looked productive but quietly drained his peace, focus, and presence. This episode challenges the belief that more opportunities equal more success and offers clarity for entrepreneurs ready to simplify, realign, and move forward with confidence.

Key Takeaways

• Why staying busy often masks avoidance, not progress
• How focusing on one core business can increase both profit and peace
• How time blocking protects momentum instead of restricting freedom
• Why FOMO fades once you commit deeply to one direction
• What it really takes to build a business that supports family, health, and presence

Resources / Links Mentioned

• The 4-Hour Workweek by Timothy Ferriss | Kindle and Hardcover
• Build with Leila Hormozi - Podcast
• My First Million | Podcast
  
  
  

About Dan Rivers
Dan Rivers is a real estate investor, REALTOR®, and the founder of Rivers Capital Group and a leader at Maven Realty. He specializes in acquiring, repositioning, and managing residential and small multifamily assets, with a focus on value-add strategies and long-term portfolio growth. Through Rivers Capital Group, Dan works with investors to identify and execute real estate opportunities, while his role at Maven Realty enables him to provide expert guidance on buying, selling, and investing. Known for his hands-on approach and market insight, Dan combines investment expertise with brokerage experience to help clients build sustainable wealth through real estate.

Connect to Dan

• Website: Maven Realty
• Facebook: Rivers Capital Group  
• LinkedIn: Dan Rivers

Connect with Us 

Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm.

Resources

Curious how much you could be saving? Try the Tax Savings Self-Assessment tool here: https://shorturl.at/4RIc0. 

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  • Live More Show Page: Live More Show
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You can earn seven figures and still feel financially stuck if your tax strategy is backward. CPA Byron McBroom reveals how entrepreneurs unknowingly overpay by default and how intentional tax planning creates freedom, optionality, and time. If taxes feel like a constant drag, this episode resets the frame. Press play and start using taxes as a lever, not a loss.

Key Takeaways

• Why high earners often overpay taxes even with a CPA in place
• How reactive tax filing quietly limits cash flow and future options
• What separates tax compliance from true tax planning
• How small structural decisions create outsized long-term impact
• Why the right tax strategy supports family, freedom, and flexibility

Resources / Links Mentioned

• Rainmaker Academy 

About Byron McBroom, CPA
Byron is a CPA with over 40 years of experience helping entrepreneurs and business owners think differently about taxes. As a partner at One Stop Tax Strategists, he specializes in advanced tax planning, income deferral, and systematized strategies that turn tax savings into long-term opportunities. His perspective is shaped by decades of real-world cases and family-run business leadership.

Connect with Byron

• Website: One Stop Tax Strategist
• Instagram: @onestoptaxstrategists

Connect with Us 

Take control of your tax strategy and start keeping more of what you earn. Learn more at www.osts.tax and book your free tax assessment here: https://calendly.com/d/cv47-9dz-krm.

Resources

Curious how much you could be saving? Try the Tax Savings Self-Assessment tool here: https://shorturl.at/4RIc0. 

Follow us on Social Media

• Facebook: 
  • Live More Show Page: Live More Show
  • Personal Page: Melanie Sikma
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• YouTube: Melanie Sikma