An Interview With Chad Silverstein
Trusting myself and my analysis has been instrumental in making my own decisions and ignoring ‘conventional wisdom’ that may not always apply.
In the world of business and within every industry, there are forward-thinking leaders who go against the status quo and find success. Their courage to take risks, embrace innovation, and inspire collaboration separates them from the competition. Until 2002, Apple’s famous slogan was “Think Different”. This attitude likely helped them become one of the most successful organizations in history. This interview series aims to showcase visionary leaders and their “status quo-breaking” approach to doing business.
As a part of this series, I had the pleasure of interviewing Joel Freudman.
Joel Freudman is the Founder of Resurgent Capital Corp., a Toronto-based boutique merchant bank focused on taking venture-stage companies public in Canada. A former securities and M&A lawyer, he has led numerous complex restructurings, refinancings, and go-public transactions. Joel now spends much of his time in the automotive repair sector, where he is Vice President of Corporate Development of Transmission Doctor, Inc. (an Aaction Automotive Group company) in southern Florida, spearheading its corporate structuring initiatives and growth-by-acquisition strategy.
Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?
I was born and raised in Toronto, Canada, the older of two boys in my family. My parents divorced when we were very young, and coming from that background, I was always a “rule-breaker” — but in terms of having way too much unfocused energy and constantly getting into trouble at school.
As I grew up and got more guidance from my parents and teachers, I gradually learned to productively focus my excess energy on academics and extra-curriculars, and eventually on my career.
From there, my path became more structured, though it would hardly be conventional once I entered the working world. I earned a Bachelor of Commerce degree (with distinction) from University of Toronto’s Rotman Commerce program, and a Juris Doctor (with distinction) from Western University in London, Ontario. I’ve also passed Level I of the Chartered Financial Analyst program.
Can you give us a glimpse into your journey into this industry and share a story about one of the most significant challenges you faced when you first started out? How did you end up resolving that challenge?
My entry into the automotive repair industry started in mid-2024 with Aaction Automotive Group, a “roll-up” (acquisition-oriented business model) targeting auto repair shops. I was looking to invest in a high-quality shop in southern Florida in connection with my relocation from Toronto to Fort Lauderdale, and that search turned up Transmission Doctor, Inc. It was a profitable business with a longstanding reputation, but like most small ‘mom-and-pop’ businesses, the information wasn’t packaged neatly for a buyer.
One of the biggest early challenges was due diligence and legal documentation. The sellers were excellent operators, but not paperwork people, and their financial reporting and general business practices weren’t built for a sale process and new ownership. At the same time, we needed to be rigorous. The way I resolved it, much like in my personal life in my younger days, was by creating structure where there wasn’t any. I built an online data room from scratch, issued a simple yet effective due diligence request list, and did deeper validation work like cash reconciliations and tax return verifications to confirm their numbers matched reality. I also quickly learned to translate what we needed into plain English so the process with the sellers — life-long auto salesmen and mechanics — stayed cooperative, not overwhelming for them.
Who has been the most significant influence in your business journey, and what is the most significant lesson or insight you have learned from them?
While there have been many people in my life who have been instrumental in my career journey, including most significantly my parents and my business partners with Resurgent Capital Corp. and Transmission Doctor, there are 2 books that have drastically shaped my thinking on taking unconventional paths to business success.
The first is The Intelligent Investor by Benjamin Graham. Although it focused on publicly-traded companies, it ultimately stresses the importance of doing your own due diligence on an opportunity, and investing (or acquiring) when pricing is favorable enough to yield excess returns — even if the market (or your colleagues) are doing otherwise. Trusting myself and my analysis have been instrumental in making my own decisions and ignoring ‘conventional wisdom’ that may not always apply to a specific situation.
The second is The Outsiders: Eight Unconventional CEOs by William Thorndike. The book is all about the best value-creating CEOs, who took very unique paths to building their business empires. They often defied critics and analysts, who cared more about outdated models and assumptions than actually doing the deep strategic thinking these CEOs did before making career-defining decisions, acquisitions, and turnarounds. Independent thinking and decision-making — sound like a familiar theme?
Learning to develop and trust my ‘gut instinct’ has been a foundation for my business success. I’m most effective at developing corporate strategy and applying it for organizational growth and success when it’s based on my own experience, analysis, and implementation.
Can you share a story about something specific that happened early on that you would consider a failure but ended up being a blessing in disguise or ended up being one of the most valuable lessons you had to learn on your own?
Early on in my foray into the auto sector, we had what felt like a real failure right after acquiring one of our auto repair shops. Within a short period, we discovered that a few employees weren’t trustworthy and were dragging down morale at their shop. My first reaction was self-doubt. I replayed the due diligence process in my head and thought, “How did we miss this before closing?”
What made it a blessing in disguise is that it forced us to learn a lesson we could only learn by living it: no matter how thorough your diligence is, culture and character reveal themselves in day-to-day operations, not on paper. Instead of sitting around worrying or facing ‘paralysis by analysis’, we treated it as an opportunity for an immediate reset under our new ownership. We moved quickly, made the tough decisions, and replaced the problematic employees with stronger performers who fit the culture better. The results were immediate. The shop ran smoother, the team dynamic improved, and we actually reduced costs because the new hires had lower hourly rates.
Leading anything is hard, especially when grappling with a difficult situation where it seems that no matter what you decide, it will have a negative impact on those around you. Can you share a story about a situation you faced that required making a “hard call” or a tough decision between two paths?
I think my previous answer really speaks to this question as well.
Aaction Automotive Group, which includes Transmission Doctor and which is now a 6-shop organization generating about $20 Million of annual revenue with nearly 80 employees, is run by only two executives: its President, who has overall decision-making authority and who also manages all day-to-day operations; and myself as Vice President of Corporate Development, where I play a supportive but leading role in forming and implementing corporate strategy, handling acquisitions, and generally accelerating organizational growth via various corporate initiatives.
We frequently face major decision points that can have competing negative — or positive — outcomes. As another recent example, we’ve had to choose between different complex, costly paths forward for a major corporate reorganization project, that involves meaningful upfront expense and management effort, albeit to set things up for more scalable growth and a more appealing exit path in the medium-term. Fortunately, scoping-out and leading corporate restructuring initiatives has always been well within my wheelhouse, from my foundational days as a securities and mergers attorney in Canada, and then over the past decade as President of Resurgent Capital. Now, as one of the two executives running Transmission Doctor, I’m getting the chance to apply that skillset to a rapidly-growing privately-owned business, allowing us to move faster and with fewer regulatory and third-party hurdles.
Ultimately, at this point in my career, I’m used to these challenges faced by organizational leaders like myself. The sooner I can identify and assess a problem, the sooner I can make a sound decision on how to best address it — and then execute relentlessly to tackle it quickly and effectively.
Let’s shift our focus to the core of this interview about ‘Successful Rule Breakers’. Why did you decide to “break the rules”? Early on, did you identify a particular problem or issue in how businesses in your industry generally operated? What specifically compelled you to address this and want to do things differently? Please share how you went about implementing those changes and the impact they had.
I decided to “break the rules” (but still follow the laws, of course!) because a lot of small businesses, especially in fragmented ‘blue-collar’ industries like auto repair, are run in a way that works for a single owner but doesn’t scale. The problem isn’t that owners aren’t talented; many, like those whose businesses we acquire, are excellent operators. The issue is that the industry is still very ‘old-school’. Reporting is inconsistent and often done on pads of paper; governance is informal; marketing is nearly non-existent; and growth often relies on instinct and individual relationships, rather than repeatable systems. That makes it hard to build a real platform, and so it also limits what caliber of capital or strategic partners you can attract — exactly the types of financing activities I’m responsible for sourcing as VP of Corporate Development.
So with Aaction, we’ve tried to do things differently by bringing institutional discipline to a blue-collar business, without killing what makes it work. Critically, at the day-to-day level, Aaction’s President — an operational mastermind — has revamped business practices and implemented repeatable processes across every imaginable function, ranging from staffing to inventory management to marketing to cost control.
At the corporate level, in an initiative I’ve championed since joining Aaction, we’re simplifying the corporate structure and governance so the organization is easier to manage as it grows, and more prepared for future investment by blue-chip financial institutions (in the case of debt financing) and sophisticated private equity players (on the equity side).
As for corporate transactions and acquisitions, which is the ‘bread-and-butter’ of my career, we built a standardized deal process. Transmission Doctor was our blueprint: I ran the due diligence process end to end, and turned our materials into reusable data room templates, request lists, and workflows, so we can execute quickly and consistently on future acquisitions — of which we’ve subsequently completed 3, with more in the pipeline. The impact has been very practical and tangible: our acquisitions close faster, surprises are reduced for us and for the sellers, and we’re seeing more inbound interest from owners who want a serious buyer that is organized and capable of closing.
In the ever-changing business landscape, how exactly do you decide when to adhere to industry norms versus “breaking the rules” and forging your own way? Can you share an example?
Great question! My thoughts on this are simple: I follow industry norms when they maintain long-term reputation and relationships and profitability, but I “break the rules” when the norms are evidently the result of laziness, bad habit, or lack of structure. For me, a good indicator to start breaking rules is when I’m told “it’s always been done this way,” without any underlying justification as to why.
In auto repair, it’s usually one mechanic buying a shop from another, and the deal gets done on a handshake. In legalese, a norm is completing acquisitions quickly with minimal due diligence and inadequate legal protections and contracts, resulting in greater risk for both seller and buyer. Ironically, we chose to break that norm (or rule) by adding some more procedural and contractual protections (or rules). With Transmission Doctor, I pushed for a level of diligence and financial validation that’s unusual for buyers our size, even though it took more effort from us up front, and more cooperation from the sellers. That decision paid off two-fold. Not only did it help us confirm the business was truly sound — and as I mentioned earlier, we still ran into some staffing issues, so no decision is foolproof — but also it became the blueprint for Aaction’s standardized ‘deal engine’ we now reuse, so our acquisitions can still close quickly but with lower risk and friction to both parties.
What guidance or insight can you offer to new entrepreneurs trying to follow existing and accepted industry norms while at the same time trying to differentiate themselves in the marketplace?
I suggest taking another look at my previous answer. In most industries, customers don’t reward creativity if it makes the basics or their economics worse. So be conventional on the fundamentals: reliability, transparency, quality control, and treating people fairly. That’s your base.
Then differentiate in the parts of the business that actually compound. Build simpler and more effective systems, innovate methods for faster execution, and develop better decision-making matrices than your competitors. In a fragmented industry like auto repair, for example, most shops compete on price or personality. A platform can differentiate by being easier to deal with, more consistent, and more professional behind the scenes, without losing the local feel.
A practical way to do this is to pick one or two areas where you have a competitive edge and build around them, especially if they have customer-facing benefits that will flow up to strengthen your business’s overall reputation. It might be process, customer communication, hiring, financing, or how you evaluate opportunities. Start small, prove it works, then standardize it so it becomes repeatable. Differentiation that can’t be repeated is just a one-trick pony. Differentiation that becomes a system is a real, sustainable competitive advantage. Word of mouth about excellent service and results spreads fast and is effective, especially at a grassroots level.
Here is the main question of our interview. To make an impact, you have to champion change, get creative, and take risks. Please think back about the decisions you’ve made that have helped your business get to where it is today, and share your top 5 strategies or decisions that helped you succeed by doing things differently. If you can, please share a story or example for each.
1. We brought institutional discipline to a blue-collar roll-up.
Instead of growing like a typical small owner-operator, we’ve been cleaning up the corporate structure and governance relatively early, working with professional advisors. It’s not glamorous, but it makes the platform easier to manage, easier to finance, and more credible to serious investors.
2. We made our first deal our blueprint, then standardized everything.
As I mentioned earlier, when we acquired Transmission Doctor, we ran a sophisticated and complete process: due diligence, proper contracts, financial valuation models, bank financing, and seamless closing execution. Then we reused the best parts, tweaked for the few issues that did arise, and turned it into a repeatable acquisition engine, so each new target starts with the same templates and workflow. Given that Aaction Automotive employs a roll-up strategy (i.e. growth through acquisition), including when I joined alongside the acquisition of Transmission Doctor, this is arguably my single highest-leverage contribution to the organization’s growth trajectory.
3. We moved from “find a deal” to “build a pipeline.”
After the first acquisition, sourcing from conventional channels seemed to have dried up. Instead of assuming there was limited acquisition runway ahead, I widened our search net, built more broker and mechanic relationships, and did direct ‘cold-call’ outreach, often dropping in unannounced to busy garages to get to know their owners. That shift to a more wide-ranging and aggressive approach resulted in a stronger pipeline, giving us more choice in targets.
4. We learned to speak operator language without losing rigor.
Most auto shop owners aren’t paperwork people and don’t respond well to finance jargon and legalese. I learned to maintain my professional instincts and protocols, but to communicate in plain language and speak to the interests of potential sellers, so deals don’t stall on avoidable friction or distrust.
5. We treat financing relationships as something you build early.
A big part of corporate development is not waiting until you need money to start a conversation with potential financing partners. In my role as Vice President of Corporate Development with Transmission Doctor, supporting the broader Aaction Automotive Group, I’ve spent time building relationships with banks, private equity firms, brokerages, and high-net-worth investors, well in advance of potential capital raises and strategic investment discussions, so that when the time comes we’re continuing an existing dialogue, not starting from zero. This also builds trust and credibility, as contacts can measure our progress and execution alongside developing the relationship.
As a leader, how do you rally others to align with your vision? Also, how do you identify those who may not be fully committed or even silently sabotaging or undermining your efforts? What steps do you take to address these situations?
Just to quickly take a step back, anything personnel-related starts with having the right people in place. I learned this the hard way, as well as from excellent management books like The Outsiders which I mentioned earlier. Recruiting and hiring are part science, part art. I always hire for the best people I can find, and compensate them well and treat them fairly. Trust and loyalty are critical to building an effective, engaged workforce. Ideally, I want to both rely on the people I work with, while also being able to have a friendly off-the-cuff conversation with them. That tends to be a recipe for a successful, enjoyable workplace.
I rally teammates by making the vision practical, not abstract. Most people don’t get motivated by slogans. They get motivated when they understand what we’re building, what is expected of them, and how their work connects to a real outcome — ideally one from which they also stand to directly benefit. So I keep the message simple, repeat it often, and back it up with clear priorities, roles, and follow-through. When people see consistency, decisions made with forethought, and standards applied fairly, alignment usually happens naturally.
As for identifying trouble spots, I watch behavior. The signs are usually recurring: missed deadlines, “forgotten” follow-ups, recurring excuses and complaints, low motivation, and subtle negativity that spreads uncertainty and demoralizes others. Silent sabotage is rarely dramatic. It shows up as slow-walking, selective communication, and doing the bare minimum.
When that happens, I address it directly and early. First, I clarify expectations and ask a simple question: are you aligned with what we’re trying to do, and if not, what’s the real issue? Sometimes it’s a misunderstanding or a role mismatch and we can fix it with clearer accountability. But, if it’s an attitude or integrity problem, I don’t let it linger. I make the hard call quickly and get rid of whoever is dragging us down, because one negative attitude can quickly undermine the energy and morale of the rest of the team.
Imagine we’re sitting down together two years from now, looking back at your company’s last 24 months. What specific accomplishments would have to happen for you to be happy with your progress?
Two years from now, I’d be very satisfied if we’ve proven Aaction Automotive is a real growth platform, not just a collection of individual shops. Concretely, that means a simplified, unified organizational structure; cohesive and integrated back-office functions and systems; the successful acquisition and integration of several more high-quality, high-revenue shops; and growing interest in joining our platform, both from additional auto shop sellers and from institutional financing partners like banks and private equity. We also have several internal metrics, in terms of number of shops, revenue level, and EBITDA (operating earnings) margins, that we’re targeting.
You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
I’d love to see more people practice intentional giving at the local level. You don’t need to be ultra-wealthy to create meaningful impact; what matters is being thoughtful. Pick a small number of grassroots organizations that you believe are well-run and high-impact, learn how they actually use resources, and support them consistently over time, whether through volunteering your time, making charitable donations, or helping them increase their visibility and reach.
Even modest contributions can compound when they’re targeted and sustained. If more people treated giving the way they treat investing, doing a bit of diligence and backing what works, I think the ripple effect in communities would be enormous.
How can our readers continue to follow you or your company online?
You can follow me on LinkedIn at https://www.linkedin.com/in/joel-freudman-67321852/.
And if you’d like to see what we’re building in the auto repair space, check out Transmission Doctor at www.tdfix.com.
Thank you so much for sharing all of these insights. We wish you continued success and good health!
Thank you as well, I appreciate the opportunity. Always happy to chat with Authority.
About The Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Successful Rule Breakers: Joel Freudman Shares Key Insights was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.