Today’s guest is someone I’ve admired for a while now not just for what he’s building, but for how he’s building it. Tim Olson is the managing partner of Aspire Finance, and in this episode, we walk through his journey from a commission-only equipment finance rep to launching a nationwide lending firm, acquiring companies, and raising capital for real estate syndications all while staying grounded, humble, and hungry.

We talk about fast money, medium money, slow money, how to align your business with your values, and why consistency and curiosity are two of the greatest traits any entrepreneur can develop.

This one’s for the connectors, the visionaries, and the people who want to own their life instead of just making a living.

Key Talking Points of the Episode

00:00 Introduction

02:51 Who is Tim Olson? 04:27 Tim’s start in banking, sales, and relationship-building

09:25 When the entrepreneurial bug started to bite

11:01 The power of curiosity and genuine connection

15:19 Learning to speak less, listen more, and win trust

18:32 Fast, medium, and slow money

21:38 Building Aspire Finance with Kelly Garrett & team

28:10 The value of partnerships and staying in your lane

31:22 Acquiring legacy businesses from retiring owners

33:22 Focusing on culture when acquiring businesses

36:15 Structuring acquisitions: SBA loans, seller financing, rollovers

39:36 Raising capital for multifamily real estate

43:14 Vetting real estate operators and avoiding bad deals

47:20 Fitness, cold plunges, and daily mental reps

55:21 How to enforce accountability in your life

01:02:33 Get in touch with Tim!

Quotables

“Fast money puts food on the table. Medium money builds wealth. Slow money creates legacy.”

“You’re not a better entrepreneur because you grind harder. You’re better because you get clearer.”

“I don’t want to just raise money—I want to build trust that lasts decades.”

Links

Tim Olson

[email protected]

https://www.facebook.com/timothylee87

https://www.instagram.com/tim.olson.1/

608B Capital

https://608bcapital.com

There’s a common message floating around the entrepreneurial space: “You’re the average of the five people you spend the most time with, so cut out anyone who’s not helping you grow.”

I don’t buy it.

In this weekly ramble, I break down why I believe some of the most valuable people in your life may have nothing to do with your business but everything to do with your heart, identity, and sanity. These are the friends who were there before the titles, before the growth, before the success and they’ll still be there when the spotlight dims.

If you’ve ever felt the pressure to “cut ties” just to rise higher, this episode is your reminder that you can build big without burning the people who built you.

Key Talking Points of the Episode

00:00 Introduction

01:42 Challenging the narrative: “Cut out your old friends to grow”

02:25 JJ’s Joke of the Week

03:11 The real value of long-term friendships

05:01 My friends are on completely different paths

07:02 Why I protect my inner circle and who gets in my bubble

08:40 What old friends do for your heart and mind

09:32 Weak-minded people need to cut ties

11:08 The annual Outer Banks trip: friendship > ROI

14:33 Friendship = fulfillment, not friction

17:29 Why I keep my core circle small

20:05 Never forget where you came from

23:08 Stop buying the myth: you’re not the sum of five people—you’re you

Quotables

“If I applied the logic of cutting people out who aren’t helping my growth, I’d lose every one of my best friends.”

“You can’t tell me that laughing around a campfire doesn’t add value to my life.”

“My biggest ROI? A weekend in the Outer Banks, belly laughing with guys I’ve known since high school.”

Links

608B Capital

https://608bcapital.com

In this episode, I sit down with one of the most electric humans I know—Jen Josey, the self-proclaimed (and trademarked) Bestower of Badassery. Jen’s a former music teacher turned real estate mogul, coach, podcaster, author, and all-around badass. We get into everything from her first deal off Craigslist, to co-founding multiple real estate companies, launching a mastermind for investors, and how margaritas and bold moves shaped her career.

We talk about burning the ships, building confidence, raising capital, making mistakes, and still showing up with energy, humor, and grit. If you’re on the fence about chasing something bigger or you just need a little push to get out of your own way—Jen’s story is your wake-up call.

Key Talking Points of the Episode

00:00 Introduction

01:57 JJ’s Joke of the Week

02:24 Who is Jen Josey?

06:55 Making the decision to get into real estate full-time

08:30 “Everything’s negotiable”—how she landed her first deal with confidence

11:52 Dealing with doubt, critics, and the “perfectly good job” mindset

14:11 From flips to short-term rentals to the Acorn Agency

16:43 Building momentum with quick wins and small flips

20:30 Investing in yourself through coaching, masterminds, and communities

24:35 The power of networking and peer accountability

28:35 Becoming a podcast host, coach, and speaker

32:35 Coaching with Tarek El Moussa and sharing the stage with her TV inspiration

35:15 Why your network builds your influence

38:13 Energy as a superpower and what it costs to give 110%

40:37 The journey of writing From Beginner to Badass

44:48 Why publicly declaring goals unlocks massive accountability

48:03 The REIGN Mastermind: coaching, classes, and connections

52:45 Jen’s 2025 BHAG: Building a couples-only tiny home retreat

Quotables

“Entrepreneurship is living a few years of your life like most people won’t, so you can live the rest like most people can’t.”

“I didn’t just burn the ships—I burned the trucks that brought them.”

“If you’re not getting uncomfortable, you’re not pushing hard enough.”

Links

Jen Josey

https://www.therealjenjosey.com/

https://www.facebook.com/therealjenjosey

https://www.instagram.com/therealjenjosey/

Real Estate Investor Growth Network Podcast

https://reign.libsyn.com/

This one’s personal. In today’s episode, I’m diving deep into the role your marriage plays in your entrepreneurial success—not just as a support system, but as a strategic advantage most people overlook. I’m breaking down what it’s meant for me to be married to a spouse who’s never tried to change me, always supported me, and gives me the space to fully be who I am.

From emotional bandwidth and shared freedom to the kind of trust that lets you swing big in business without fear, I’ll share how my marriage to Katie has shaped every success I’ve had.

This episode is a challenge to check in on your relationship, set a new standard, and maybe most importantly—protect the partnership that protects everything else.

Key Talking Points of the Episode

00:00 Introduction

01:59 JJ’s Joke of the Week

02:19 My marriage to Katie: 16+ years of partnership

04:06 A billionaire’s answer: “My spouse is my greatest asset”

05:48 What it means to be understood and calmed by your spouse

08:49 Early relationship talks: loving who we were without trying to change it

12:11 Understanding what your spouse wants

14:47 Emotional bandwidth: the most underrated asset in business

17:32 Creating space for personal freedom and mutual respect

20:35 Encouraging each other’s solo trips and friendships

27:13 Spouse support is the foundation of business courage

30:48 Advice for anyone in a relationship or considering marriage

Quotables

“You only have so much mental bandwidth. If your spouse takes up half of it, what’s left for your dreams?”

“Real support means giving each other space to live fully—and come back better.”

“If you’re constantly negotiating freedom with your partner, you’re already losing your edge.”

Links

608B Capital

https://608bcapital.com

In this episode, I sit down with my good friend Joe Robey, a humble, no-BS entrepreneur who went from growing up with little to leading a thriving nationwide fiber optics company while raising six kids and living life on his terms.

We talk about everything from overcoming adversity, to how sports built his confidence, to how he uses business as a tool to bless others. Joe gets real about his rough childhood, why that struggle became his superpower, and what it means to design a life where family always comes first.

If you’re a parent, business owner, or just someone trying to balance ambition with being present—this one is for you.

Key Talking Points of the Episode

00:00 Introduction

02:55 JJ’s Joke of the Week

06:30 Who is Joe Roppe?

08:00 Transitioning from building properties to fiber optics

12:50 Starting a nationwide company from scratch (with no credit!)

14:34 How sports helped Joe gain confidence in life

20:14 Teaching kids grit when they grow up without struggle

26:20 The importance of curating adversity for your children

29:48 Navigating life with a blended family

34:30 Scaling the business to 80+ employees

37:07 Redefining success: It’s not about money

40:14 What being motivated by your family should look like

46:03 How Joe and his wife balance entrepreneurship and parenting

52:23 Laser-focusing your work time to stay present at home

54:19 The game-changing power of forced accountability

59:48 The joy of hunting with your kids (and the best quote ever!)

01:04:50 How to connect with Joe and his team

Quotables

“If I’m going to preach discipline to my kids, I better be in the gym before they wake up.”

“At the end of the day, I want my kids to say, ‘My dad showed me how to live right.’”

“Money is just a tool. Legacy is the mission.”

Links

Joe Roppe

https://www.facebook.com/elitecutoverconnections

https://www.facebook.com/joe.roppe.1

https://www.instagram.com/jroppe4/

608B Capital

https://608bcapital.com

In this episode, I’m diving deep into something we all face—adversity—and why it’s not something we should run from, but something we should lean into. I’ll share how the hardest moments in my life became the very foundation for my discipline, resilience, and success—and why I believe your toughest battles are actually building you.

I also break down why it’s crucial to teach our kids how to face adversity head-on, instead of shielding them from every hardship. Because one day, we won’t be there to protect them—and the best thing we can do is equip them to stand strong when life hits back.

This one is raw, real, and meant to challenge you to reframe pain as preparation. Burn the ships, embrace the fire, and let’s talk about what’s really shaping you.

Key Talking Points of the Episode

00:00 Introduction

02:03 JJ’s Joke of the Week

03:22 How adversity teaches us lessons for the future

06:37 Explaining the concept of adversity to your children

09:05 The impact of helping your children build the right mindset towards adversity

11:39 What we do to shape our children’s mindset and teach them independence

13:40 Why independence is important in overcoming adversity

15:20 Different kinds of adversity you can encounter in life

17:29 What it means to curate adversity for your children

21:18 The value of making your children understand that losing comes with lessons

23:41 How being so focused on winning can impact your child’s perspective

27:11 The kind of support your children actually need from you

31:19 Why you need to guide your child through adversity

Quotables

“If we allow them to do that, then we’re not teaching them to be able to struggle through things, to be able to figure things out.”

“They have to learn to deal with the consequences that come with small decisions they make.”

“Losing is applauded in our house, as long as they did so with max effort, as long as they did so with the attitude of “I’m gonna try harder”.”

Links

608B Capital

https://608bcapital.com

In this episode of Burning the Ships, I talk with Philip Thai, who left a stable software engineering career to build wealth through real estate investing, lending, and business acquisitions. He shares how he burned the ships, scaling from his first wholesale deal to managing 60+ flips, 80+ wholesale transactions, and commercial properties.

Philip also reveals how he’s using seller financing to acquire businesses with little to no money down. If you’re ready to leave corporate life, scale your income, or master creative investing, this episode is packed with real-world strategies you can apply today.

Key Talking Points of the Episode

00:00 Introduction

02:39 Who is Philip Thai?

07:12 Philip’s transition from software engineer to full-time investor

10:18 The importance of taking action after education

15:40 The role of mentorship & masterminds in fast-tracking success

19:03 Paying for education: Why investing in yourself is a game-changer

25:04 The biggest opportunity in business buying right now

31:06 The “Annuity Structure”

32:37 The shift to buying strip malls and commercial properties

38:51 The key to balancing business, real estate, and passive investing

43:05 Why social media is the new business card

48:54 Journey vs. Destination: Why you need to enjoy the process

53:25 How Jiu-Jitsu and business share the same mental game

Quotables

“I had enough pain to make a change. If you don’t have enough pain, you don’t have a reason to change.”

“If you invest in yourself, you can shrink a 5-year learning curve into just 12 months.”

“You can buy a business just as creatively as real estate—sometimes even better financing terms.”

Links

Philip Thai

www.youtube.com/@philliphthai

https://www.instagram.com/philliphthai

New Breed Investors

www.skool.com/newbreed

608B Capital

https://608bcapital.com

Welcome back to Burning the Ships, where we go all in on taking risks, pushing boundaries, and eliminating excuses. Today, we’re diving into grit—the unshakable quality that separates those who succeed from those who quit too soon. You’ve heard the word before, but what does it actually mean?

In this episode, I break down G.R.I.T. into four essential traits: Gratitude, Resourcefulness, Intentionality, and Tenacity. Through personal stories of adversity, lessons from my father’s struggles, my mother’s resilience, and real-life setbacks, I’ll show you why grit is the ultimate predictor of success—whether in business, sports, or life.

If you’ve ever struggled with doubt or setbacks, this episode is for you. Learn how to move with purpose, turn failures into fuel, and push through when success is just around the corner. No matter your path—entrepreneur, athlete, or go-getter—embracing grit will transform your journey. Burn the ships, commit fully, and get to work.

Key Talking Points of the Episode

00:00 Introduction

01:46 JJ’s Joke of the Week

02:10 What is grit?

03:49 G is for Gratitude

05:50 How my father’s struggles shaped my mindset and leadership

08:35 Learning resilience through financial and emotional hardships

11:20 R is for Resourcefulness

14:17 I is for Intentionality

16:55 T is for Tenacity

19:07 Lessons from competition, sports, and how to bounce back after failure

22:55 How jiu-jitsu has reinforced my mindset on grit and perseverance

24:44 The profound moment with my mom that changed my entire perspective on struggle

29:04 Finding gratitude in setbacks

32:14 The difference between those who succeed and those who quit too soon

Quotables

“Most of the good in me came from the hard times I went through. And I wouldn’t change a thing.”

“You don’t need to be the smartest, fastest, or strongest. But if you’re the one who refuses to quit, you’ll always have a chance to win.”

“If you quit now, you’ll never know how close you were to breaking through.”

Links

608B Capital

https://608bcapital.com

From bartending to building a multimillion-dollar brand—that’s the story of Dan Oliver, founder of Dan-O’s Seasoning. In this episode of Burning the Ships, Dan breaks down how he turned a homemade seasoning blend into a national brand sold in Walmart, Kroger, and 20,000+ retailers across the U.S.

We get into the grind behind the growth—from flea markets to viral TikTok success, why having no Plan B made all the difference, and how sticking to his vision landed him major investors. If you’re an entrepreneur, hustler, or just someone chasing a dream, this episode will light a fire under you and prove that betting on yourself is always the right move.

Key Talking Points of the Episode

00:00 Introduction

01:02 JJ’s Joke of the Week

03:03 Who is Dan O?

11:43 Where Dan’s entrepreneurial spirit comes from

15:35 Dan’s journey into entrepreneurship

21:31 The “lightbulb moment”: Realizing Dan-O’s could be a business

27:03 Building a brand: Selling at farmer’s markets and small retailers

33:11 The importance of storytelling, branding, and standing out in the market

35:06 How one viral TikTok video changed everything for Dan-O’s

42:45 Scaling Dan-O’s: Landing deals with Walmart and Kroger

49:17 Building a business through resourcefulness

54:24 Lessons from The Secret

59:01 Where the content ideas for Dan-O’s come from

01:01:32 The future of Dan-O’s Seasonings

01:06:51 Dan’s advice for aspiring entrepreneurs

Quotables

“I was never going to give up. It was Dano’s or nothing.”

“The best brands don’t just sell a product—they tell a story. That’s what makes people connect.”

“I didn’t have a plan B, and that’s what made investors believe in me.”

Links

Dan-O’s Seasoning

https://danosseasoning.com/

Instagram:

https://www.instagram.com/danosseasoning/?hl=en

YouTube:

https://www.youtube.com/channel/UCyP9TINtZzvTJfN69GskqLQ

___________________________

The Secret

https://www.thesecret.tv/

608B Capital

https://608bcapital.com/

Work-life balance? It’s a myth—unless you create it with intention. In this episode of Burning the Ships, I break down how I went from grinding 24/7 to building a life where business and family actually work together.

I’ll share the hard lessons I learned, why most entrepreneurs get this completely wrong, and how simple shifts like time-blocking and setting real boundaries can change everything. If you feel stuck between your career and personal life, this episode will give you the mindset and strategies to take back control—without slowing down your success.

Key Talking Points of the Episode

00:00 Introduction

01:43 JJ’s Joke of the Week

02:27 The cliche of achieving work-life balance

03:29 Different careers = different challenges

06:03 Transitioning from corporate to full-time entrepreneurship

08:16 Unlearning work habits from corporate to focus on family

11:43 Realizing what being truly present means

15:12 The power of time-blocking

18:26 Creating more productivity in less time with the right structure

23:03 Planning business activities around family life

27:36 The impact of setting boundaries when time-blocking

Quotables

“If you’re not intentional with your time, someone else will be.”

“I was physically there with my kids, but my mind was in a completely different world.”

“Time-blocking isn’t just for business—it’s the key to actually being present in your life.”

Links

608B Capital

https://608bcapital.com/