Episode 32: What Comes After the Exit? Building Again with Travis Hevelone

What happens after you build the company, sell it, and discover the next chapter is not waiting neatly on the other side? For Travis Hevelone, the answer involved an unexpected layoff, time to decompress, a failed business experiment, and a return to the work he does best: solving operational problems.

In this episode, Mike and Zach sit down with engineer and entrepreneur Travis Hevelone to explore the full journey from startup founder to acquired CEO and back to business owner. Travis shares how he co-founded jobZology in 2012 and built PathwayU, a science-based career-guidance platform that reached more than one million users across over 200 institutions.

We dig into the long search for a buyer, the moment private equity reached out, and the six months of due diligence that followed. Travis explains why inbound interest felt fundamentally different from chasing prospective acquirers, how he handled the process while still running the company, and what it was like to become an employee after the sale.

One of our biggest takeaways is that an exit does not automatically answer what comes next. After being laid off 10 months into the transition, Travis took time off before experimenting with a print-on-demand T-shirt business. The model generated sales but remained unprofitable and left too much control in the hands of a changing advertising algorithm.

You’ll also hear how that experience led to SingletrackOps, where Travis combines 25 years of operations experience with AI to automate repetitive work for trades and home-service businesses—helping owners replace disconnected apps and manual processes with lightweight tools that give their teams hours back every week.

• Why Travis chose entrepreneurship at age 39
• How jobZology grew into a national career-guidance platform
• Why inbound acquisition interest changed the conversation
• What six months of private-equity due diligence required
• Why founders need a plan for life after the sale
• What an unexpected layoff taught Travis about loyalty
• Why his print-on-demand business could not become profitable
• How platform risk can take control away from an owner
• How AI can turn conversations into working software
• Why automating repetitive work gives trades businesses time back

“I’m a startup guy. I like to know everybody.”

“Sometimes you’re loyal to a fault.”

“All play is not good for me. My engineering brain needs to solve problems.”

“You can actually build real software that solves real problems just by talking.”

Travis Hevelone is an engineer and operations leader who loves solving problems. He has spent approximately 25 years in operations, running IT consultancies and a network operations center before becoming a technology founder.

In 2012, Travis co-founded jobZology and built PathwayU, a science-based career-guidance platform that grew to more than one million users across over 200 institutions. The platform also earned national recognition and an invitation for Travis and his team to brief officials at the White House.

Travis sold the company to PeopleGrove in 2023 and remained through a 10-month transition before being laid off. After taking time to reassess what came next and experimenting with a print-on-demand business, he recognized that his strongest advantage remained in engineering, operations, and practical problem-solving.

Today, Travis runs SingletrackOps, which combines his operations experience with AI to help trades and home-service companies eliminate repetitive work, connect fragmented processes, and give owners more time to focus on customers, sales, and the work they enjoy.

Find Travis Hevelone on LinkedIn, visit SingletrackOps, or email [email protected]

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Episode 31: Why More Deals Won’t Fix Your Money with David Richter

What if doing more deals is making your financial problems worse? Revenue, door count, and deal volume may look impressive, but none of them matter if the business owner is not keeping money, building reserves, or paying themselves consistently.

In this episode, Mike and Zach sit down with David Richter, founder and CEO of Simple CFO and author of Profit First for Real Estate Investing. David shares how working inside a company that grew from five to more than 25 deals per month exposed a painful truth: the business was spending 26 deals’ worth of money for every 25 it closed.

We dig into how that experience, along with similar conversations with investors at every level, led David to build Simple CFO. After seeing how basic financial clarity transformed one investor’s business, he adopted the Profit First framework and began helping real estate operators understand their numbers, protect cash, and stop living from deal to deal.

One of our biggest takeaways is that real estate investors are not merely playing the game of real estate—they are playing the game of money. Profit First makes that game visible by assigning every dollar a purpose through dedicated accounts for income, owner compensation, profit, taxes, operating expenses, and other people’s money.

You’ll also hear how Simple CFO evaluates a client’s current and target allocations, why reserves need their own protection, how owners can use AI and assistants to reclaim time, and why the simplest place to begin is one new owner-compensation account funded with just one percent of every sale.

• Why more deals do not guarantee more profit
• How David discovered the need for Simple CFO
• Why real estate investors are playing the game of money
• How dedicated bank accounts create financial control
• Why other people’s money needs its own account
• How Profit First protects owner pay and taxes
• The difference between current and target allocations
• How to prepare for unpredictable real estate expenses
• Why good money habits can extend into personal finances
• How to start with one account and one percent

“It doesn’t matter if you’re doing lots of deals if you’re not keeping any of it on the back end.”

“We’re playing the wrong game in our mind.”

“The nice thing about real estate—and the predictable thing—is that it’s unpredictable.”

“The only way you can fail this system is you don’t implement it.”

David Richter is the founder and CEO of Simple CFO and the author of Profit First for Real Estate Investing, a version of Mike Michalowicz’s Profit First system designed specifically for real estate investors.

Across 10 years in real estate, David played a key role in closing more than 850 deals spanning wholesale, fix and flip, BRRRR, rentals, lease options, owner finance, turnkey properties, and other exit strategies. That operating experience allows him to translate financial concepts into language real estate investors can use.

While helping grow one operation from five to more than 25 deals a month, David watched large sums of money come in and go right back out. After serving in roles across sales, marketing, operations, property management, project management, and finance, he found his calling in helping investors understand where their money actually goes.

Through Simple CFO, David and his team provide bookkeeping, Profit First implementation, tax support, and fractional CFO guidance. His mission is to help real estate investors gain financial clarity, build cash reserves, pay themselves consistently, and stop making money while feeling broke.

Learn more about David Richter at Simple CFO, get his free book and resources at simplecfo.com/gift, or email [email protected]

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Episode 30: Building a Bankable, Sellable Business with Matthew Meehan

What makes a business fundable today and transferable tomorrow? For Matthew Meehan, the answer starts with clean financials, disciplined cash management, the right capital structure, and a company that can create value without depending entirely on its owner.

In this episode, Mike and Zach sit down with Wall Street veteran and business advisor Matthew Meehan to explore how small and midsize companies can access capital, scale responsibly, and prepare for an eventual exit. Matthew shares his unconventional path from barely graduating high school to spending nearly two decades on Wall Street and helping build a full-service investment bank.

We dig into his decision to leave the firm, move to Florida, and enter cash-flow-based small-business financing. When COVID threatened the businesses he had funded, Matthew began helping owners navigate PPP, EIDL, and ERC programs—an experience that evolved into a broader mission to help companies improve their books, become bankable, and build lasting enterprise value.

One of our biggest takeaways is that the right financing depends on the borrower, the purpose, and the lender’s appetite. Matthew explains the differences between traditional bank lending, SBA financing, alternative funding, private placements, and SPVs, along with the financial records and credit profile owners need before approaching capital providers.

You’ll also hear why a good exit strategy is simply good business strategy, what makes a company transferable, why preparation should begin 12 to 24 months before a sale, and how owners can design a life and business they will not need to escape from.

• How Matthew went from stockbroker trainee to investment-bank owner
• Why partnership agreements must be put in writing
• How COVID reshaped his small-business lending model
• What makes a company bankable
• How alternative cash-flow financing works
• Why SBA standards vary from bank to bank
• How lender appetite affects approvals
• The difference between SPVs and private placements
• Why business exits require 12 to 24 months of preparation
• How to build a transferable business instead of buying a job

“Make sure you have everything on paper.”

“Treat everybody the same way, because you don’t know where somebody is gonna be.”

“It doesn’t matter what you think. Trade what you see, and pivot along the way.”

“A good exit strategy is just good business strategy.”

Matthew Meehan is the CEO of Shield Advisory Group, a full-service consulting firm that helps small and midsize businesses obtain access to credit and capital. Through a big-picture assessment, he helps clients understand financing options, market dynamics, and the steps required to support revenue growth and increased market share.

Before founding Shield Advisory Group, Matthew spent nearly two decades on Wall Street and held Series 7, 63, 24, and 99 registrations. He directed the East Coast expansion of multiple boutique investment-banking firms and later became an owner of a full-service investment bank.

Leveraging his network, outside-the-box thinking, and knowledge of traditional and alternative finance, Matthew has raised capital and contributed to the growth of private and publicly traded companies across numerous industries. His experience spans commercial and equipment financing, asset-based and SBA financing, credit lines, private placements, bridge and acquisition financing, SPVs, reverse mergers, PIPEs, and cash-flow financing.

Matthew is also a certified exit planner who helps owners improve operations, clarify their financial position, unlock transferable value, and prepare their companies for a future sale. He co-hosts The Liquid Lunch Project, a podcast focused on practical business growth, funding, and strategy.

Find Matthew Meehan on Instagram, listen to The Liquid Lunch Project, or email [email protected]

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Episode 29: From Massive Scale to Smarter Growth with Sam Primm

What happens when rapid growth stops being the goal and recurring profit becomes the priority? After building multiple real estate companies, scaling to dozens of employees, and owning a portfolio valued as high as $50 million, Sam Primm learned that more is not always better.

In this episode, Mike and Zach sit down with real estate investor and educator Sam Primm to unpack how a normal guy from Missouri built a large operation without inherited money or an entrepreneurial family. Sam shares how Rich Dad Poor Dad changed his view of money and how experienced partners shortened the learning curve.

We dig into the mistakes that came with scaling quickly, including an over-improved hotel that continues to lose money and a cost structure that grew faster than the business could sustain. Those lessons pushed Sam and his team toward stabilization, tighter financial reporting, fewer distractions, and business models with steadier recurring revenue.

One of our biggest takeaways is that delegation still requires structure. Each company has an operating leader, profit-based incentives, financial oversight, and regular meetings to review metrics and solve problems. Sam also explains how careful tenant screening and in-house maintenance helped make property management a lower-risk business.

You’ll also hear how Sam grew an audience of roughly 3.5 million followers by publishing every day for six years, why quantity must come before quality, how authenticity outperforms overproduction, and why consistent action matters more than trying to predict which post will succeed.

“Growth doesn’t always mean more companies, more people. It can mean more recurring revenue. It can just mean more profit.”

“You need quantity, then you need quality.”

“You just gotta be willing to fail for a while or not be seen.”

“The lesson learned is just post.”

Sam Primm is a real estate investor turned educator who remains actively involved in real estate through a group of operating companies spanning acquisitions, flipping, wholesaling, property management, education, and lending connections.

Sam’s flipping company buys and sells more than 250 houses a year. He has built a real estate portfolio valued as high as $50 million and currently owns approximately $40 million in real estate after strategically selling selected assets.

His businesses include Faster House, Midwest Property Group, and Faster Freedom. Together, they combine active real estate operations, management of hundreds of rental units, educational programs, and connections between borrowers and lending partners.

Sam has also built an audience of approximately 3.5 million followers across social media, where he shares practical lessons about real estate, debt, leverage, entrepreneurship, and business growth. His direct, consistent approach helps everyday people understand how to begin investing in real estate.

Find Sam Primm on Instagram, visit Faster Freedom, or email [email protected]

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Episode 28: The Get Rich Slow Reality of Multifamily Investing with Marianna Osipenko

What if buying the property is only the starting line? Multifamily investing can build lasting wealth, but the real work begins after closing—with renovations, vacancies, operating expenses, property management, and the patience to stabilize one asset before moving to the next.

In this episode, Mike and Zach sit down with real estate investor Marianna Osipenko to explore the practical realities of building an out-of-state multifamily portfolio. Marianna shares how her early interest in real estate, business-brokerage experience, and financial training helped her learn to examine the numbers behind a deal instead of accepting a polished offering memorandum at face value.

We dig into her transition from two- to four-unit properties in Massachusetts to larger value-add assets in Ohio and Kentucky. A difficult renovation during COVID showed Marianna that the work required for a property does not rise in proportion to its unit count—and that more doors under one roof can create valuable economies of scale.

One of our biggest takeaways is that ownership cannot be outsourced. Even with excellent property managers, Marianna stays close to leasing, contractor bids, renovations, and performance. She treats management as a partnership, takes work off the team’s plate when she can, and keeps enough control to pivot quickly when costs or market conditions change.

You’ll also hear how she evaluates markets, why family-sized units can support longer tenancies, how flips provide a creative outlet and occasional cash boost, and why real estate rewards patient, disciplined investors rather than anyone expecting instant passive income.

“The amount of work is not proportional to the number of units.”

“No one’s gonna take as good care of your property as you are.”

“Congratulations, you got a property. Now the real work begins.”

“It’s not a get rich fast. It’s a get rich slow scheme.”

Marianna Osipenko graduated from Babson College in 2003 and later returned for her MBA, completing extensive coursework in real estate finance and investing.

She spent the first 15 years of her career with George & Company, one of New England’s premier business appraisal and brokerage companies. That experience strengthened her ability to analyze financials, understand varied business models, negotiate, and assemble complex transactions.

In 2019, Marianna followed her longtime passion and transitioned into full-time real estate investing. Since then, she has grown an out-of-state portfolio of value-add multifamily properties ranging from 12 to 42 units, with a focus on disciplined underwriting, hands-on asset management, and thoughtful market selection.

Marianna’s communication, negotiation, and financial skills allow her to analyze opportunities quickly, decode complicated financials, and see the potential in a deal. She remains closely involved with her property-management teams and takes ownership of the decisions required to renovate, stabilize, and operate each asset.

Find Marianna Osipenko on Facebook and Instagram, or email [email protected]

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Episode 27: Organic Marketing That Actually Creates Customers with Danielle Hollembaek

What if your biggest marketing numbers are the ones that matter least? A viral post may earn millions of views without creating a single customer, while a focused podcast, email list, or educational post can keep generating qualified leads for years.

In this episode, Mike and Zach sit down with Danielle Hollembaek, co-founder of Provato, to talk about building an organic marketing engine around trust, consistency, and measurable results. Danielle shares how she worked her way from radio DJ and video editor to marketing leadership, learning every seat along the way and gaining the empathy needed to lead strong creative teams.

We dig into why founders need a recognizable personal brand and how short-form content can introduce people to your work while podcasts, YouTube, and books build deeper trust. Danielle explains how a useful free resource can move an audience from rented social platforms to an email list you actually own.

One of our biggest takeaways is that vanity metrics do not equal revenue. The right 5,000 followers can be more valuable than millions of disconnected views. Real marketing performance comes down to qualified leads, booked calls, sales, and knowing which content moved someone through the pipeline.

You’ll also hear how Danielle kept an airport hospitality company profitable during COVID, recovered a disabled Facebook account, integrates business and family life, and plans to scale Provato through thoughtful hiring, clear culture, and a data-driven marketing audit.

“Every brand has to have a face now.”

“You need to own your list, which is all the emails and all of the numbers that you collect.”

“It’s not like you have to have a big following to get leads through your social media presence.”

“If you don’t want to work with me, we shouldn’t be working together.”

Danielle Hollembaek is the co-founder of Provato, a fractional CMO firm built for founders who have been burned by broken agency promises.

With over a decade of marketing experience, she has climbed from video editor to Chief Marketing Officer in less than five years by obsessing over one thing: results that actually move revenue. She has kept travel businesses profitable during COVID, scaled seven-figure companies to eight figures, and grown startups into six-figure companies.

Throughout her career, Danielle has generated thousands of qualified leads organically and trained teams to own their own marketing functions. Her experience across hands-on production, strategy, and leadership shapes an approach grounded in empathy for every role on a marketing team.

Today, she partners with founders to build predictable pipelines and prove every marketing dollar with data, not vanity metrics.

Find Danielle Hollembaek on Instagram and visit Provato

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Episode 26: Building the Expedia of Racquet Sports with Daren Hornig

What happens when a real estate investor stops choosing an asset class first and lets the opportunity reveal what it can become? For Daren Hornig, that mindset has led from commercial leasing and telecommunications to billion-dollar real estate development and an AI-powered racquet-sports platform.

In this episode, Mike and Zach sit down with entrepreneur and investor Daren Hornig to unpack a career built around curiosity, resilience, and scale. Daren shares how he grew a fiber-optic infrastructure company to 500 employees, weathered the dot-com collapse, returned to real estate, and diversified across office, residential, retail, and industrial properties.

We dig into the acquisition of the Port Washington Tennis Academy and how a real estate opportunity became a growing sports business. After partnering with Sportime and establishing Sportime Port Washington, home to the John McEnroe Tennis Academy, Daren expanded further into pickleball facilities across the Northeast.

One of our biggest takeaways is Daren’s approach to vision: stay open enough to let the opportunity define the highest and best use. That same thinking led to CourtsApp, a marketplace designed to help players discover and book courts while helping facilities fill unused time and make smarter decisions.

You’ll also hear how CourtsApp plans to use AI through its “Hey Courtney” agent, why customer data can unlock dynamic pricing and better service, how platform businesses scale without owning every underlying asset, and why Daren still chooses building and growth over retirement.

“I let opportunity drive my vision, and I don’t let my vision drive opportunity.”

“I like building. I like being dynamic. I like going for it.”

“The data is the treasure trove.”

“Life’s too short. I don’t need to buy headaches. I don’t need to have bad partners.”

Daren Hornig is the founder and Chief Executive Officer of CourtsApp, the first AI-powered booking platform built for racquet sports such as tennis, pickleball, padel, and squash.

Daren is also Managing Partner of Hornig Capital Partners, bringing over 35 years of experience as a real estate broker, telecommunications entrepreneur, investor, and developer. Since founding HCP in 2013, he has acquired and developed over $1 billion in office, residential, retail, and industrial properties.

In 2023, Daren acquired the famed Port Washington Tennis Academy and partnered with Sportime to establish Sportime Port Washington, home to the John McEnroe Tennis Academy. Following an $8 million renovation, the facility now features 13 tennis courts, 12 pickleball courts, and two golf simulators. He later partnered with Sportime to expand dedicated pickleball facilities throughout the Northeast.

A 1989 graduate of the University of Maryland, College Park, with a bachelor’s degree in Business Marketing, Daren resides in New York and Florida. When he is not building companies, developing properties, or opening new pickleball facilities, you can find him on the courts or the slopes.

Find Daren Hornig on LinkedIn, visit CourtsApp, or email [email protected]

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Episode 25: Why Paying More Can Make You More with Jon Nolen

What if the cheapest option is actually the most expensive mistake? From rental repairs to lead generation, masterminds, software, and even flights, it all keeps coming back to one idea: value matters more than price.

In this episode, Mike and Zach sit down with real estate investor Jon Nolen to dig into the hidden cost of cutting corners in real estate, business, and life. We talk about what it’s really like to manage a rental portfolio, including the benefits of using both in-house management and outside property managers. There’s a lot to learn from seeing how other people run their systems, especially when it helps improve your own.

We shift into why landlords need to take better care of their tenants. Slow repairs, cheap materials, and poor service don’t save money in the long run. They lead to vacancies, make-readies, and lost cash flow.

One of our biggest takeaways from this conversation is around leads. Cheaper leads can create more work, more rejection, and more burnout. Better leads may cost more upfront, but they can convert faster, save time, and produce stronger returns. 

You’ll also hear about flipping versus holding, the value of high-level masterminds, and how a real estate CRM can bring the whole property lifecycle together.

“It’s not always best to get the lowest price. Sometimes it’s better to pay more.”

“Pay more. Get better leads, get better software, get better everything.”

“You don’t get into real estate to add more stress to your life.”

“Value your time more, because you’re spending a lot of time to save nickels.” 

Jon Nolen is a United States Marine Corps veteran, software entrepreneur, and high-volume real estate investor. 

Since 2012, Jon has successfully navigated hundreds of transactions and built a substantial portfolio of over 120 rental properties. Unlike many founders who have moved away from the field, Jon remains actively engaged in the Oklahoma City market, where he continues to acquire new rentals and execute high-end property flips today. 

Recognizing the technical gaps that slow down growing teams, Jon founded Pete REI, a custom-built CRM and automation platform. Drawing on his background in corporate IT and software development, he built Pete as a true investor-designed operating system that leverages "edge" AI to streamline lead management and operations. 

Beyond his business ventures, Jon is an active pilot, a Brazilian Jiu-Jitsu practitioner, and a dedicated father of three. He is passionate about helping the modern investor move from "hustle" to "high-performance" by solving complex systems problems with authentic, scalable technology.

Find Jon Nolen on Facebook and Instagram

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Episode 24: How to Turn Your Business Into a Transferable Asset with Paul Cronin

Most business owners think they’re building an asset, but might actually just be building a job for themselves. What’s the difference between a business that survives and one that thrives? It comes down to common patterns that hold businesses back and simple principles that create lasting value.

In this episode, Zach and Mike sit down with Paul Cronin, a coach who works with companies ranging from a few million to hundreds of millions of dollars in revenue. We explore why corporate success doesn’t always translate into entrepreneurial success, how great leaders learn to coach people at every level, and why being “coachable” may be the single most important trait a business owner can have.

We also dig into an often overlooked topic: transferability. If your company depends entirely on you, do you really own a business, or does the business own you? You’ll learn how buyers evaluate risk, why some companies bring higher valuations than others, and how understanding the four capitals can dramatically improve both business performance and long-term wealth creation.

We also chat about the biggest mistakes founders make when preparing for a future exit, the importance of building systems that work without the owner, and why waiting until you’re ready to sell is often far too late.

“Don’t tell me what you’re saying yes to, tell me what you’ve said no to that probably was a better idea.”

“Your job as the owner is to create a highly transferable asset.”

“The number one reason companies struggle is not having the right people in the right seats.”

“If nobody wants what you have, it has no value.”

Paul Cronin helps owners of $7M-$150M companies escape the Founder's Trap, unlocking 3 to 8 times their enterprise value. Stop chasing EBITDA at the expense of engineered transferability, optionality, and your freedom. 

Find Paul Cronin on LinkedIn

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Episode 23: The Hidden Challenges of Sudden Wealth with Joseph D. Warren

Most people spend their lives trying to make more money, but what happens when a large amount arrives all at once? Whether it’s selling a business, receiving an inheritance, cashing out company stock, or another major financial windfall, a sudden wealth event can create opportunities and mistakes that impact the rest of your life.

In this episode, Zach and Mike sit down with Joseph D. Warren, a financial planner specializing in helping people navigate these life-changing moments. He explains why the biggest threat isn’t usually the money itself, but the emotional decisions people make after they receive it.

We discuss why creating rules before major financial events happen can help you avoid costly mistakes and why having a strategy in place before the money arrives is often more important than what you do afterward. You’ll also hear why successful investors build a team around them instead of trying to become experts in everything. 

Our conversation also dives into business ownership, the importance of tracking how you spend your time, and why your business should support your life rather than consume it. You’ll also hear practical tips about naming savings accounts, preparing for future investment opportunities, maintaining proper asset allocation, and why diversification still matters. 

“The biggest financial mistakes happen when emotions take over.”

“You want the plan in place before the money arrives, not after.”

“Your business should support your life, not become your life.”

“Ethics are the number one thing that you have.”

Joseph D. Warren is the co-founder of Financial Planning HQ, LLC, a boutique firm providing truly comprehensive financial strategies for a limited number of clients. 

He serves fast-growing business owners with meaningful real estate holdings as their Financial CEO. Joseph coordinates tax, legal, lending, and cash flow so you can focus on your business and the things that matter more than money. 

In his free time, when he's not helping clients, you can find Joseph at the gym lifting weights, reading Sci-Fi, or spending time with his wife and two kids (a toddler and newborn). 

Find Joseph D. Warren on YouTube | LinkedIn | TikTok | Instagram

Call Joseph D. Warren on 210-444-2128 

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