Randy Tobbe started his entrepreneurial journey with a power washing business. 20 years later, he's built and sold two software companies.

The first software company sold to a company that eventually owned by Zillow.

The second started out as a side project to help a friend build a CRM, which later became LionDesk. In 5 years it went from 0 customers to 165,000 monthly paying users - they sold three years ago.

Now Randy runs RanToro Group, to help companies in telehealth, ecommerce, and legal use AI to cut costs and get their time back.

In this episode of Beyond The Hustle, we covered:

→ Why Randy’s first exit was “mediocre” but the second wasn't

→ How and why he built a live dashboard in 15 minutes for a client

→ Why enterprise software is losing to tools companies build themselves

→ The short window before AI levels the playing field for good

→ Why chasing the Instagram flex is the wrong game entirely

My big takeaway: the businesses that’ll win the next five years are the ones willing to build a decent version first, fix it later and get known in the market.

Thanks to Randy for making time between running his own company. Appreciate you being here, brother.

Chapters

00:00 Intro

01:09 From power washing to software, twenty years in business

01:58 Building Realty Commander by accident and selling to Zillow

05:08 Why the first exit was mediocre and LionDesk wasn't

08:23 The ripple effect, impact beyond the paycheck

10:12 Why he skips the Instagram flex

12:56 Imposter syndrome, even for the guys who've done it before

22:23 AI, efficiency, and the coming creative renaissance

30:24 Why enterprise software is losing to homemade tools

40:28 Building Mission Control, a live dashboard, in 15 minutes

~~~

This episode is powered by Drive Creative:

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Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

John Spreitzer runs Green Lantern Pizza. He has seventeen stores across Metro Detroit, two more opening, and a franchise company being built behind the operation.

He opened his Berkeley location in February 2020. But three weeks later, Covid shut it down. Everything he had was tied up in his store. He didn't even know if he'd lose his house…

They made it through and learned from the experience. Now he's building a franchise model, aiming to hit a hundred stores over the next ten years.

In this episode of Beyond The Hustle, we covered:

→ Growing from one location to seventeen stores

→ Why minimum wage is the biggest threat to the business

→ The real story behind the Pepperoni King brand

→ Marketing in the age of AI and managing reviews across every location

→ Why he helps competitors down the street instead of ignoring them

Thanks John for making the time to sit down and and share with our listeners!

Chapters

0:00 Intro

1:04 Meet John Spreitzer and the story of Green Lantern Pizza

3:00 Franchising 17 stores and building the company behind them

5:51 Off the grid bear hunting in Quebec

9:48 The vision to scale to 100 stores

12:13 Minimum wage, food costs, and the economics of running pizza shops

18:29 Road construction, real competitors, and supporting the neighborhood

20:44 Cup and char pepperoni and building the Pepperoni King brand

30:43 Marketing in the age of AI and managing reviews across 17 locations

35:25 Almost losing everything during Covid, and his advice for anyone starting a restaurant

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Ivan Katz has run Great Lakes Landscape Design for 37 years.

He's been embezzled from, close to bankruptcy, and had run-ins with the IRS… all from putting trust in the wrong people and not having the right controls in place.

But between 2021 and 2024 he nearly tripled his revenue and headcount, by fixing the people-side of the business and creating a culture of honest feedback with great core values.

On this episode of Beyond The Hustle, we covered:

→ How a paper route and a flower planting side hustle turned into a real business

→ Surviving embezzlement, IRS trouble, and near bankruptcy

→ Building a culture around feedback and core values

→ Getting sober at 30 and replacing addiction with endurance racing

→ Why communication is the hardest skill in business and in life

Thanks Ivan for making the time to sit down and talk shop. Appreciate you, man!

Chapters

00:00 Intro

01:00 Planting flowers for four bucks a flat

09:56 Near bankruptcy, an embezzlement, and owning it all

12:39 Fixing the people problem with feedback and core values

16:18 Building a culture around honesty, safety, and innovation

19:05 Getting sober and finding structure in exercise

23:47 The mindset behind finishing a race no matter what

30:23 What sobriety actually taught him

38:19 Being honest about recovery with everyone

42:07 What's next: the Summer Summit and the human element in an AI world

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Teo Bogdan came to Michigan from Romania at 10 years old.

He grew up to get a mechanical engineering degree and land a good corporate job at a Japanese auto supplier. But sitting in that office, and looking out over the parking lot at his dream car while feeling completely trapped, he knew it wasn't his endgame.

After a single real estate flip netted him $50,000 in two weeks, the illusion of corporate security shattered. He walked away to pursue business on his own terms.

Today, Teo is rewriting the playbook on "Entrepreneurship through Acquisition." Two and a half years ago, he bought A Plus Heating and Cooling, and he’s scaling it the right way: by treating it like a system, not a job.

What we covered:

→ Why the scale of American business looked so "insane" to him at 10

→ The specific moment he realized he was done with the corporate grind

→ Why he avoided starting from scratch and chose to acquire an existing HVAC company

→ Building a shop that creates techs from high school grads.

→ Why answering the phone within 5 minutes matters more than your SEO

→ Why you need to watch out for fake local companies

Thanks Teo for sharing the blueprint on how to build a business that runs without you… Appreciate you dude!

Chapters

00:00 Intro

1:00 From Romania to a mechanical engineering degree

3:52 Stuck in the corporate grind at Denso

5:12 From real estate to trades

5:55 Buying A Plus Heating and Cooling

9:29 The growth strategy: master HVAC before anything else

11:27 Hiring and training techs the right way

19:06 The flip that changed everything

28:12 Answering the phone, AI search, and why reviews win the job

38:09 Watch out for fake local companies

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Jeff Schulmeister spent decades behind the scenes of some of the biggest manufacturers in the country, building engineering databases for Siemens and BorgWarner, while running side businesses on his own time. A limousine company. A laundromat. A home health care company.

Now, Jeff’s buying companies; he walks through the exact math on why buying a cash flowing business can outperform the stock market, and why he'd rather fire an owner on day one than trust them to stick around.

In this episode we covered:

→ How Jeff financed his first limousine with no money down at 20 years old

→ Getting laid off from Siemens and hired the same day by the guy he trained

→ Why the laundromat business almost went bankrupt before it worked

→ Buying Omni Home Health Care

→ What Jeff learned about financing acquisitions through SBA loans

Thanks Jeff for making the time to sit down and share the whole story. Glad to have you here man!

Chapters

00:00 - Intro

01:08 - Financing his first limousine with no money down

04:38 - Driving for Aretha Franklin's parties and Motown connections

06:54 - Teaching himself AutoCAD to break into design

09:43 - Laid off from Siemens, hired the same day

11:28 - Costing Siemens $800,000 out of pure revenge

19:11 - Building a laundromat out of an old dry cleaning plant

22:47 - Nearly bankrupt and the hundred dollar bill that changed it

25:45 - Buying Omni Home Health Care and the money the last owner missed

34:45 - Why buying a business beats investing in the stock market

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Mya Stone runs Stone Capital Partners, a people first M&A firm out of Grand Rapids doing buy and sell side deals for founder owned businesses doing $1M-$100M a year.

After walking away from law, Mya built and sold a hospitality startup, then helped grow a body shop company up to 47 locations. When that business got hit with a lawsuit, she had to rebrand every location overnight. She sold that business and later started Stone Capital Partners on the single idea that the right people are the real asset.

Here's what we covered:

→ How a Harvard advisory board told her she wasn't ready to be CEO

→ Scaling and losing a body shop rollup to a lawsuit

→ Why most business owners have no idea what their company is worth

→ Being a young woman in a room full of suits has an advantage

When owners build a business they rarely think about what it's worth or who it's for once they're gone. Mya's whole career is proof that the people side of a deal matters as much as the numbers.

Thank you Mya for making the time to come on and go Beyond The Hustle with us!

Chapters

0:00 Intro

01:47 Raised by grandparents, Harvard by 16

04:47 Walking away from a Harvard law career

06:19 Building and selling a Boston hospitality startup

10:08 Told to lead people, not run the company

11:28 Scaling a body shop rollup to 47 locations

21:48 The real messes inside family owned businesses

25:19 Telling employees about a sale, and the fridge that changed everything

32:47 Cold calling, urgency, and the truth about the silver tsunami

47:36 Being a young woman in a room full of suits

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Aaron McCarthy spent 20 years in corporate IT before deciding he was done climbing someone else's ladder.

In 2018 he convinced his wife for them to take a SBA loan and started Maven IT out of a borrowed front office in exchange for free support. No staff. Just him and a laptop.

In this episode we covered:

→ Why he picked recurring revenue as his model before he even had a business

→ How a cold call to a Smoothie King franchisee turned into a 50-location relationship

→ What actually happens operationally when you acquire a business

→ The cybersecurity basics small businesses skip until they get hacked

→ What he's looking for in his next acquisition strategy

Aaron’s got a simple filter: will it produce recurring revenue? Can I improve the operations? Can I learn it myself first? When those boxes check, he moves.

Aaron, thanks for coming in and sitting down on Beyond The Hustle. Appreciate you dude!

Chapters

0:00 - Intro

1:00 - Who Aaron is and what Maven IT does

2:30 - 20 years in corporate and the recurring revenue light bulb

5:05 - Why he bought a commercial cleaning company

6:15 - Transitioning ownership and what he inherited

9:00 - Starting Maven IT at 40 with an SBA loan

12:25 - How the Smoothie King relationship started

15:15 - How the MSP space has changed and where new growth comes from

20:05 - AI, cybersecurity, and what's actually happening in the space

25:34 - What small businesses should do right now about cybersecurity

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

Spotify → https://open.spotify.com/show/033gI3Y3rhCbWjbPqfVmMf?si=3ad1a107ca2244fa

Apple → https://podcasts.apple.com/us/podcast/beyond-the-hustle/id1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Matt McAlpine went from washing kegs at a cider farm to running Michigan's largest cannabis beverage operation.

The early days at Blake’s Hard Cider were tough… Their first big bet (getting non-smokers into dispensaries with a 2mg drink) didn't land the way they planned.

They adjusted and deployed 150 refrigerators into dispensaries which doubled average sales per store.

And they went from near zero to manufacturing 60%-80% of all cannabis beverages in Michigan.

In our episode we covered:

→ How Matt scaled Blake's Hard Cider from 10,000 to 1.3 million cases

→ Why the "get canna-curious consumers into dispensaries" strategy failed

→ The play that unlocked 51 dispensaries and doubled their average order size

→ How Michigan stacks up as a cannabis beverage market

→ How 37,000 Michigan liquor stores present the real opportunity

Matt thanks for coming by the studio to record and share your story of struggles and successes!

Chapters

00:00 Intro

01:00 Who is Matt McAlpine

03:14 Chrysler and the manufacturing leadership program

05:50 Leaving corporate for Blake's Hard Cider

07:53 Scaling Blake's from 10,000 to 1.3 million cases

10:05 Blake's Beverage Company and acquiring regional cider brands

13:40 How Emerald Canning Partners was formed

15:37 Building the facility and the early product launch struggles

20:35 Who the real cannabis beverage consumer is

24:24 Brand partners, the full portfolio, and owning the fridge

30:38 Michigan's market share and the 37,000 liquor store opportunity

36:43 Why cannabis beverages beat alcohol for recovery

44:00 Operations, team building, and the hire slow fire quick mentality

50:00 What fires Matt up and where ECP is headed

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to listen?

https://pod.link/1896663240

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Kelly grew up in Eight Mile in Michigan, the same streets Eminem rapped about.

His house was absolute chaos: a drunk stepfather, a drunk mother who once stabbed her husband and set the house on fire, and a kid who learned to survive by reading the room before anything else. By the time he got to college, he was selling drugs, racking up arrests, and lying on every job application about his two felonies. Then he went to jail.

That four months in a cell changed him forever: Kelly realized he was good at sales and started a telecom brokerage from nothing. He built it into a multimillion-dollar company even without a website.

Kelly wrote Harder Than Life. Then Happier Than Life. He built a podcast and an AI-driven cybersecurity company.

And he keeps going back into the hard stuff because he's learned feeling it is the only way through it.

In this episode, we tackled:

→ Why alcohol and drugs are always a symptom of the disease

→ The childhood trauma that drove his addiction for decades

→ His TLC framework for rebuilding your mind, body, and life

→ What faith, surrender, and a specific prayer to God have done for his business

→ Why the thing you keep avoiding is your actual portal to growth

Kelly told me you can't heal what you're unwilling to reveal… Everything opened up once he stopped sugarcoating how bad things really were.

Thank you Kelly for bringing this level of honesty into the room!

Chapters

0:00 - Introduction

1:00 - Kelly's Background: Eight Mile, Eminem, and Growing Up Poor

3:30 - Selling Drugs, Getting Arrested, and Two Felonies

6:45 - Jail, the Wake-Up Call, and the First Honest Job

10:30 - Dillon Shares His Own Story: Heroin at 18

14:00 - Faith, God Moments, and the Power of a Specific Ask

17:00 - Why Kelly Stopped Drinking and What Happened Next

21:30 - The 15 Days of Anxiety: Healing Childhood Trauma

25:00 - What Being Happier Than Life Actually Looks Like

27:30 - The TLC Framework: Train, Learn, Coach

32:00 - Finding Common Ground in a Divided World

35:30 - Final Message: TLC, Truth, and How to Get Both Books Free

~~~

This episode is powered by Drive Creative:

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to watch?

YouTube → https://youtu.be/T8LzJkBrfAc

Do you have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show

Early on in his sales career, Dan received a $0 commission check. With a wife and kids at home to take care of, it was a moment that changed him forever…

Dan Russell is VP of National Sales at Trion Solutions, overseeing payroll, HR, and benefits for over a million employees across the globe. But before any of that, he was a mortgage banker trying to do right by his clients in an industry that stopped letting him.

In this episode we tackled:

→ Why Dan walked away from mortgage banking at its peak

→ What a $0 commission check teaches you that success never will

→ How Trion handled an employee dying on a client's floor in real time

→ Why asking for help is the most underrated skill in business

→ What community investment actually looks like when no one's watching

A huge takeaway from my time with Dan was that asking for help isn't a sign you don't have it together… it's how people who actually have it together got there.

Dan, thanks a ton for coming in and being so open about the hard moments. Appreciate you dude!

Chapters

0:00 - Introduction & Welcome

1:00 - What Dan Does at Trion Solutions

1:55 - How Dan's Company Got Acquired

2:49 - The Mortgage Banking Days

4:35 - The $0 Commission Check

5:43 - Why Dan Left Banking and Found PEO

8:20 - Sink or Swim: Learning a Brand New Industry

10:55 - Why You Have to Know Your Product

21:55 - What the Best Business Owners Have in Common

27:48 - When a Client Called About a Dead Employee

34:36 - Community Work: Covenant House and Beyond

38:45 - Homeless Youth and the "Lost Generation"

41:53 - Advice to His Younger Self

46:39 - Stop Trying to Do It Alone

47:07 - Why Starting Matters More Than Being Ready

49:39 - Gratitude as a Practice, Not a Feeling

~~~

This episode is powered by Drive Creative

🌐 https://drivecreativeagency.com/

Subscribe for more conversations with entrepreneurs and innovators who push Beyond The Hustle

Prefer to watch?

YouTube → https://youtu.be/nPJQmvcdogY

Have a story to tell? We’d love to hear from you!

Learn more about being a guest on Beyond The Hustle by visiting https://www.beyondthehustle.show