Raw and Relentless w/ Bo DePaoli

Episode 114

AI has made it easier than ever to build software. But if everyone can build a product, how do you actually get customers, grow revenue, and build a company worth owning?

On this episode of Raw & Relentless with Bo DePaoli, Bo sits down with David, a serial entrepreneur whose previous startup was acquired by Sequoia Capital and who now leads The Swarm, an AI-powered relationship intelligence platform.

David shares how he scaled his previous recruiting business to approximately $1 million in annual recurring revenue in nine months, what he learned working inside Sequoia Capital, and why the startup playbook is changing faster than ever.

Bo also opens up about building his own AI-powered gym management software, creating automation for his businesses, and deciding whether to bootstrap, raise venture capital, or build toward an eventual exit.

In this episode, you'll learn:

• Why customer acquisition and distribution are becoming harder than building software

• How warm introductions and referrals can outperform traditional cold outreach

• What early-stage investors look for beyond revenue

• Why bootstrapping and keeping equity may beat raising millions

• Whether AI could make a billion-dollar one-person company possible

• How founders can use AI agents to automate operations and sales workflows

• Why your existing professional network may be your most underused business asset

• How to think about SaaS growth, startup valuations, and potential exits

  
  

Connect with David:

LinkedIn: David Connors

Episode 113

What if the biggest weakness in your company's security isn't the technology, but the person behind it?

Charles “Chuck” Peterson spent 20 years in Army counterintelligence, where understanding human behavior could mean the difference between protecting lives and putting them at risk. From legally breaking into secure military facilities to building relationships in Iraq, Chuck learned how people think, how they can be influenced, and why deception isn't always what it looks like.

Today, Chuck works in counterintelligence at Microsoft and has turned his knowledge of psychology into a mentalism and leadership business.

In this episode of Raw & Relentless, Bo DePaoli sits down with Chuck to uncover the psychology behind human behavior, the warning signs of possible deception, and why people are often easier to exploit than technology.

In this episode:

• How Chuck used social engineering to break into secure military facilities

• Why body language and eye contact can be misleading when spotting deception

• How military intelligence techniques apply to business, leadership, and influence

• The difference between influencing someone and manipulating them

• How Chuck uses mentalism to demonstrate the power of human psychology

Chuck also shares what it was like joining the Army during 9/11, his experiences in Iraq, and how he went from military intelligence to corporate security and entrepreneurship.

Whether you're building a business, leading a team, negotiating deals, or simply trying to understand people better, this conversation will challenge the way you think about trust, communication, and influence.

Connect with Charles “Chuck” Peterson:

The Veteran Mentalist

Website: www.veteranmentalist.com

Email: [email protected]

Subscribe to Raw & Relentless with Bo DePaoli for conversations on entrepreneurship, leadership, business growth, and the mindset behind success.

Episode 112

What makes a lifelong skeptic change his mind about God? And how does that transformation shape the way he leads a multibillion-dollar business?

On Episode 112 of Raw & Relentless with Bo DePaoli, Bo sits down with Richard Krauland, former CEO and current chairman of a financial holding company that Richard says has grown to $3.3 billion, and author of The Bridge from Science to God.

Richard spent roughly 24 years identifying as an atheist, studying mathematics, philosophy, and science in search of answers. Then, at age 40, he finally opened the Bible. What happened next changed his beliefs, his relationship with money, and his approach to leadership.

In this conversation, Richard shares how a decision to start giving money to someone in need was followed by a series of unexpected checks in the mail. He also explains how being fired after refusing a board member's request led him to a new leadership opportunity, where he helped grow a banking and insurance business through acquisitions and organic expansion.

Bo challenges Richard on the historical reliability of the Bible, the relationship between science and faith, and how spiritual beliefs influence decisions in the business world.

In this episode:

• Why Richard identified as an atheist for 24 years

• The Bible-reading experience that changed his beliefs

• His personal argument for reconciling science and God

• The unexpected money he received after he began giving

• Getting fired for refusing something he believed was unlawful

• Growing a financial company through seven acquisitions

• The servant leadership philosophy he used as CEO

• Why helping employees succeed can improve business performance

• The difference between financial success and personal fulfillment

  
  

Whether you're an entrepreneur, business owner, investor, skeptic, or someone questioning the relationship between faith and success, this conversation explores what happens when personal convictions collide with money, power, and leadership.

Connect with Richard!

Email: [email protected]

Book: The Bridge from Science to God — available through Google, Apple, Amazon, Barnes & Noble, Kindle

Episode 111:Artificial intelligence is making it easier than ever to build software, automate operations, and scale a business. But there's one massive problem most entrepreneurs are overlooking: their data is a mess.

In this episode of Raw & Relentless, Bo DePaoli sits down with Ilan Man, founder of Paradox Machines, to break down what business owners need to understand before throwing more money at AI tools and automation.Ilan has spent nearly two decades working in data and technology. Now he's helping mid-market companies solve the infrastructure problems that prevent them from getting real value out of artificial intelligence.

Bo also shares his experience using AI to build custom gym management software and potential SaaS applications at a fraction of what traditional software development once cost.Inside this episode:

• Why AI gives businesses inaccurate answers
• How messy business data undermines automation
• Why custom software development is becoming more accessible
• When entrepreneurs should build their own tools versus hire specialists
• How to avoid expensive enterprise data platforms you don't need
• What AI means for the future of business operations and entrepreneurship

The bottom line:AI can make building technology cheaper and faster. But if your systems, processes, and data are broken, adding more technology won't automatically fix your business.If you're a business owner, entrepreneur, investor, or founder looking to use AI for real operational leverage, this conversation is worth your time.Subscribe to Raw & Relentless with Bo DePaoli for conversations about entrepreneurship, business growth, real estate investing, technology, and building long-term wealth.Connect with Ilan Man:Website: ⁠paradoxmachines.com⁠LinkedIn: Ilan Man

Episode 111:

Artificial intelligence is making it easier than ever to build software, automate operations, and scale a business. But there's one massive problem most entrepreneurs are overlooking: their data is a mess.

In this episode of Raw & Relentless, Bo DePaoli sits down with Ilan Man, founder of Paradox Machines, to break down what business owners need to understand before throwing more money at AI tools and automation.

Ilan has spent nearly two decades working in data and technology. Now he's helping mid-market companies solve the infrastructure problems that prevent them from getting real value out of artificial intelligence.

Bo also shares his experience using AI to build custom gym management software and potential SaaS applications at a fraction of what traditional software development once cost.

Inside this episode:

• Why AI gives businesses inaccurate answers

• How messy business data undermines automation

• Why custom software development is becoming more accessible

• When entrepreneurs should build their own tools versus hire specialists

• How to avoid expensive enterprise data platforms you don't need

• What AI means for the future of business operations and entrepreneurship

The bottom line: AI can make building technology cheaper and faster. But if your systems, processes, and data are broken, adding more technology won't automatically fix your business.

If you're a business owner, entrepreneur, investor, or founder looking to use AI for real operational leverage, this conversation is worth your time.

Subscribe to Raw & Relentless with Bo DePaoli for conversations about entrepreneurship, business growth, real estate investing, technology, and building long-term wealth.

Connect with Ilan Man:

Website: paradoxmachines.com

LinkedIn: Ilan Man

Episode 110:

Seth Bader spent nearly 20 years building his Atlanta law firm—but some of his biggest lessons came when the business started growing faster than the systems and culture could keep up.

At roughly 10 years in, the firm had around 30–35 employees and $7–8 million in revenue. Within 18 months, the teamhad grown past 100, eventually reaching around 150 employees. That growth created new problems around leadership, culture, accountability, client acquisition, and maintaining the standards that made the company successful in the first place.

In this episode:

●      How Seth scaled from 30–35 employees to more than 100 in roughly 18 months

●      Why rapid growth diluted parts of the firm's culture

●      Why leadership becomes dramatically harder as a company scales

●      The difference between leading 10 people and leading 150

●      How AI and offshore talent helped Seth operate with a leaner team

●      Why rebuilding a damaged culture takes time

●      How customer acquisition costs can destroy margins

●      Why personal injury law has become brutally competitive

●      The economics behind high-volume professional service businesses

●      Why trust still matters in a transactional-looking industry

●      What Seth learned after nearly 20 years of entrepreneurship

●      Why scaling isn't automatically the same thing as building a better business

Seth also breaks down how AI is changing legal operations, why customer acquisition has become significantly more expensive, and why entrepreneurs have to evolve as leaders when their companies outgrow their direct influence.

Connect with Seth Bader:
Bader Law
Email: [email protected]
LinkedIn: Seth Bader

Episode 109:

Jon Ostenson walked away from corporate America looking for something more entrepreneurial. What he found was a worldof businesses most investors completely overlook: non-food franchises.

On this episode of Raw & Relentless, Bo DePaoli and Jon break down why entrepreneurs are investing in “boring” businesses like home services, senior care, pool cleaning, property services, asphalt, septic, and other industries that are difficult to replacewith AI.

In this episode:

●      Why Jon believes non-food franchises are being overlooked

●      The “boring” businesses attracting investor interest

●      What it actually costs to buy a franchise

●      How SBA financing can reduce the cash needed upfront

●      What a $500K franchise investment could potentially look like

●      Owner/operator vs. semi-involved ownership

●      Why the management team behind a franchise matters

●      How geography and demographics impact franchise success

●      Why larger franchise portfolios can attract different buyers

●      Jon's failed business and the lesson it taught him about complexity

●      How to know if your existing business could become a franchise

●      Why the first 5–10 franchisees can make or break a new franchise system

Jon also explains why buying into aproven system can offer entrepreneurs something starting from scratch can't:existing processes, support, data, training, and a community of owners alreadysolving the same problems.

Connect with Jon Ostenson:
FranBridge Consulting
Website: franbridgeconsulting.com
Book: Non-Food Franchising

Episode 108:

Lane Kawaoka went from working as an engineer and buying a handful of rental properties to participating in over $2 billion in acquisitions and building a real estate portfolio that reachedroughly 10,000 units at its peak.

On this episode of Raw & Relentless, Bo DePaoli sits down with Lane to break down what has changed in real estate investing and why many of the deals that worked a few years ago simply don't pencil today.

Lane gets into rising cap rates, negative rent growth, overbuilt markets, syndication mistakes, passive investing, oiland gas, tax strategy, and why diversification became a priority after getting hit during the last real estate cycle.

In this episode:

• How Lane went from 11 rentals to thousands of units
 • Why many multifamily deals don't pencil today
 • The danger of aggressive rent-growth assumptions
 • Where Lane sees opportunity in overlooked markets
 • What passive investors should look for in a syndicator
 • Why a great fee structure can't save a bad deal
 • Real estate vs. oil and gas investing
 • Why high-income investors use oil and gas for tax benefits
 • The diversification lesson Lane learned the hard way
 • What rising interest rates could mean for real estate investors

Connect with Lane Kawaoka:

LinkedIn: Lane Kawaoka

Website: thewealthelevator.com

Book: The Wealth Elevator

Episode 107:

In this episode of Raw & Relentless, Bo DePaoli sits down with MIT-trained physicist and longtime professor Stan Zygmunt for a fascinating conversation about quantum physics, science, and the nature of reality.

Stan breaks down some of the most mind-bending concepts in physics, including the double-slit experiment, wave-particle duality, quantum mechanics, and the strange behavior of matter at the smallest scales. They explore why particles don't always behave the way we expect, what happens when we attempt to measure them, and why quantum physics continues to challenge our understanding of how the universe actually works.

Stan also shares his journey from being fascinated by science as a kid to studying physics and materials science at MIT, eventually building a career spanning nearly four decades of teaching and research.

In this episode:

●      Why the double-slit experiment is so mind-bending

●      Quantum physics and the strange behavior of matter

●      Why particles can behave like waves

●      What measurement means in quantum mechanics

●      What physics can actually tell us about reality

●      Stan's journey from MIT to nearly 40 years of teaching and research

If quantum physics, the double-slitexperiment, or the mysteries of our universe have ever fascinated you, this is an episode you don't want to miss.

Connect with Stan!

Website: valpo.edu/physics

Instagram: @valpo_phys_astro

Episode 106:

What does it actually take to scale abusiness, build great teams, and stay valuable in the age of AI?

In this episode of Raw &Relentless, Bo DePaoli sits down with corporate executive, speaker, andauthor Victoria Pelletier to break down leadership, hiring, businessgrowth, and how AI is changing the workforce.

Victoria became an executive at just 24years old and has spent her career leading large-scale business and technologytransformations. She explains why entrepreneurs become their own biggestbottlenecks, why real-world experience can beat credentials, and why humanskills may become even more valuable as AI advances.

In this episode:

• How to hire the right people to scaleyour business
• Why entrepreneurs become their own biggest bottleneck
• How Victoria became an executive at 24
• Why confidence is often mistaken for competence
• Why experience can matter more than a college degree
• The biggest mistake companies are making with AI
• Why 70% of AI's value comes from people and process
• How AI can help small businesses scale with leaner teams
• The human skills AI can't replace

Connect with Victoria:

Website: victoria-pelletier.com

Instagram: victoria_pelletier_unstoppable