Case Study #81: If At First You Don’t Succeed, Try Again (x4)

Case Study #81: If At First You Don't Succeed, Try Again (x4)You’ve most likely heard the expression, “You learn more from your failures than your successes.” Entrepreneur Josh Anhalt is living proof of that statement. He recently sold his business GreenPath Energy, but not before three failed attempts.

His company played a crucial role in the oil and gas sector, but industry changes prompted Josh to consider selling. With political uncertainties on the rise and technological advances reshaping market dynamics, he knew he had to figure out what to do next.

Recognizing the need to adapt, Josh decided that it was time to let go of the business. He didn’t get it right the first time (or the two times after that), and there are several lessons to learn from his failures.

Understanding the Oil and Gas Industry

To understand Josh’s decision to sell, it’s crucial to understand the challenges within the oil and gas industry. Politics and technology play a massive role in deciding what GreenPath could and could not do.

In 2016, market forces and political headwinds created a demand for a shift in strategy. Josh realized that scaling the business required consolidation. He needed to focus on high gross margins and assemble a team of highly technical professionals if he wanted to make it work.

Despite facing difficulties, Josh maintained a profitable business. He generated $8.2 million in revenue with a remarkable return on investment before ultimately deciding it was time to sell.

The Three Failed Attempts

Josh’s eventual success was followed only by three previous failures.

  • Attempt 1: The first deal saw Josh signing a letter of intent (LOI) without legal review which led to a flawed agreement. The deal collapsed due to issues with definitions and disparities in the interpretation of “cash-free, debt-free.”
  • Attempt 2: In the second attempt, engaging with another company revealed challenges in the earnout structure. The proposal jeopardized employees’ positions, and the acquirer’s reluctance to enter the US market further strained negotiations. It was a reminder of how much his people meant to him. Josh prioritized the well-being of his employees and rejected the deal.
  • Attempt 3: Private equity’s involvement in the third attempt brought promises of an equity roll, but caution on their part derailed the deal. Reps and warranties in the share purchase agreement proved to be contentious, which highlighted the conservative approach often taken by private equity firms.

Fourth Time’s a Charm

Josh decided on a different approach this time.

Thorough due diligence preparation — including the creation of a “data room” that held all of the necessary documents — proved crucial. The deal structure involved 90% cash upfront, 10% stock, and no earnout, which demonstrated the acquirer’s confidence in the business’s future potential. In talks, Josh replaced backward-looking scrutiny with forward-looking evaluation. He emphasizes the value of future opportunities and revenue and it worked. GreenPath was officially sold.

Key Lessons

Although the sale of GreenPath wasn’t as straightforward as Josh may have liked, it was worth it in the end. He sold his company for seven times its EBITDA figure. He also learned a lot along the way:

  • It pays to say no (sometimes): Josh built his company with one thing in mind — to make money. As such, he found it very painful when he had to reject the large sum of money in his first attempt to sell. However, the cons well outweighed the pros in that deal, so it was worth it in the end.
  • Thorough preparation is key: Josh emphasizes the importance of meticulous preparation in the business sale process. Creating a data room with all essential documents, financials, and agreements readily available streamlines the due diligence process and builds trust with potential acquirers.
  • People matter: The emotional impact of selling a business is significant, especially when it comes to the relationships built with employees and colleagues. Understanding the personal and emotional aspects of the process is crucial, and considering the impact on people is an integral part of successful deal-making.

From the importance of defining terms early and adapting to industry changes to the emotional impact on personal connections, Josh’s story is a testament to resilience, strategic thinking, and the significance of preparation in the intricate world of business transactions.

Need help preparing for your own sale but aren’t sure where to start? We can help you with that — and it won’t take us four times to get it right. Give us a call today.

Case Study #80: A Bootstrapped 8-Figure Exit

Case Study #80: A Bootstrapped 8-Figure ExitAs a refugee during the Gulf War, entrepreneur Lloyed Lobo has faced challenges that shaped his perspective on community and support. The values instilled by his family and early life experiences left a lasting impression on his approach to both business and life.

Lloyed cofounded a software application called Boast AI that’s designed to simplify the process of applying for R&D tax credits. After bootstrapping their first few years, Lloyed and his partner sold the majority of the business for a cool $23 million.

The journey from bootstrapping to an eight-figure exit was filled with the highs and lows familiar to every startup founder. Let’s take a closer look.

The Power of Growth Equity

For Lloyed and his co-founder, taking the leap with growth equity meant making a commitment to the company’s future. With this decision, they moved forward on a path to grow and expand while taking on the associated risks.

Growth equity is a crucial factor in scaling any startup. It provides the necessary capital and support to accelerate growth. This phase often involves investors taking a significant stake in the company, which can lead to a shift in the dynamics of decision-making and company culture.

The Turning Point

As more time went on, Lloyed realized that he was no longer aligned with the company’s direction. As the business shifted towards a more structured approach — and grew from a bootstrapped startup to a full-fledged corporation — he grappled with the challenges of adjusting to this new dynamic.

The toll on his mental health during this period was significant. Stress, pressure, and internal conflict pushed him quite close to the brink, and he began to reevaluate his priorities.

Lloyed ultimately decided to move his family to Dubai. Many other Gulf War refugees had moved there and he knew they would be welcomed. The massive change in environment proved to be transformative, and was just the breath of fresh air he needed.

When in Dubai, Lloyed had to make a hard decision. Although it was difficult to walk away from a company that he helped build from the ground up, it was time. The business simply didn’t align with his values anymore. After many talks with the board and his co-founder, the pair decided to sell their shares.

Surrounded by his friends and family, he rediscovered what truly mattered: community.

Reconnecting with the Importance of Community

Lloyed’s time in Dubai led him to realize the profound role that community plays in our lives. He recognized that it had been a constant thread throughout his journey, from his refugee experience to the challenges of entrepreneurship and his battle with mental health.

Today, Lloyed has taken on a new role: author. His debut, From Grassroots to Greatness: 13 Rules for Building Iconic Brands through Community-Led Growth, provides insights and practical advice for those who wish to harness the power of community.

Key Lessons

While Lloyed’s exit isn’t as traditional as some others, there remain some key lessons to learn from:

  • Reevaluate, refine, and edit: When Lloyed realized that his company no longer aligned with his values, he did something about it. It’s a reminder to constantly reflect on where you are in life and in business. If you’re unhappy, make a change.
  • Community is crucial: When the going got tough, Lloyed was able to lean on his friends and family for support. Strive to do the same and surround yourself with people willing to cheer you on — and bring you back down to reality when needed.
  • Give without expecting to get: Over the course of his entrepreneurial journey, Lloyed realized that giving without expecting anything in return can lead to great things. Selfless giving has become a central theme in his life and it’s worked out in his favor.

Through his work, Lloyed continues to pay it forward, providing a valuable resource for others in search of mentorship and insights.

Interested in exiting your own bootstrapped company? We can help. Give us a call today.

Case Study #79: Yes, You Can Sell a Service Business without an Earnout

Case Study #79: Yes, You Can Sell a Service Business without an EarnoutWhen it comes to building a successful service-based business, few entrepreneurs can match the journey of Brandon Lazar. Over the course of 15 years, he transformed a simple window cleaning operation into a thriving business that served his community. But what happens when it’s time to move on and sell that business? Well, for starters, Brandon wasn’t interested in an earnout, which meant that he had to be particular about his buyer.

The Path to Selling a Bootstrapped Business

Brandon’s story begins with the humble origins of A+ Gutter & Window Cleaning. He turned a one-man show into a thriving operation through hard work, dedication, and a relentless focus on providing top-notch service to his customers. 

An intriguing aspect of Brandon’s business is his approach to financing it. He bootstrapped his way to the top, relying only on his cash flow to fund his growth. Unlike many business owners who constantly monitor valuation multiples, Brandon decided to concentrate on steady growth and exceptional service. 

His path to success raises the question: Should valuation multiples be at the forefront of an entrepreneur’s mind during the growth phase? 

Brandon says that honestly, he wasn’t thinking about valuation because he was fully invested in growing and scaling his company on a day-to-day level. With that mindset, he grew his business to seven figures before deciding to sell. It’s something to note for all of you valuation-obsessed owners out there.

Initial Approach and Negotiations = No Deal?

It’s all about who you know, or at least it was in Brandon’s case. After a tough hiring cycle, he was approached by a potential buyer within his network. This initial conversation led to negotiations about the sale of his business. 

Brandon was upfront about his expectations, being sure to emphasize the financial terms that would make the deal worthwhile to him. The lesson here is clear: transparent communication is key during the negotiation process. 

Or, one would think. While Brandon was very clear on his end, the buyer? Not so much. He eventually requested audited financial statements, which added complexity and ultimately dragged out the process. Another lesson to note here is the importance of setting clear deadlines and managing your own expectations throughout the process.

Despite progress made throughout the negotiation and due diligence stages of the sale, the deal ultimately fell apart during a Zoom call. It goes to show how unpredictable business transactions can be. 

A New Buyer Emerges

As one door closed, another one opened for Brandon. Someone else in his network expressed interest in buying A+ Gutter & Window Cleaning. He decided to go all in on this second chance, and dove into the new negotiations. 

Now that there was a new potential buyer on the horizon, Brandon revisited the valuation of his business. He successfully negotiated a sale without an earnout clause. The deal’s structure itself, including vendor take-back financing, was carefully created to align with Brandon’s specific goals. 

Key Lessons

Brandon’s story offers three key lessons:

  • Focus on growth, not valuation multiples. Brandon’s success story highlights the importance of prioritizing growth and exceptional service over constant valuation concerns during the business’s growth phase. Instead of fixating on valuation multiples, entrepreneurs should invest their energy in scaling their companies and delivering outstanding services to their customers. 
  • Transparent communication in negotiations. Being upfront about your expectations and financial terms is essential to ensure a smooth negotiation process. Clear communication helps prevent misunderstandings and aligns both parties’ interests.
  • Be flexible when structuring a deal. Explore various deal structures to align with your specific goals to ensure a favorable outcome. Brandon’s ability to adapt and shape the deal to his liking, including negotiating the absence of an earnout clause, showcases the importance of flexibility.

We help business owners create their own ideal exit, whether you’re interested in an earnout or not. Give us a call today.

Case Study #78: When Capital One Comes Calling

Case Study #78: When Capital One Comes CallingWhen Alex Macdonald first created a product that would become Velocity Black, he was simply looking to find wonderful (and exclusive) restaurants and make them easier to find and book. By the time he helped sell his company for just under $300M, he had taken that initial idea and refined it into a 24/7/365 AI-assisted private concierge service, which is something Capital One wanted to have for its products and services.

How Did the AI Help?

Velocity Black guaranteed a one-minute response time for all requests. They were able to do this by building a strong personalized profile of the customer and then allowing the AI to cross-reference that profile when building a request (e.g. customer loves Thai food and when the customer asks to find an excellent restaurant in a given city, the AI might then suggest, among other options, a Thai restaurant). A human would then take the AI suggestions and begin interacting directly with the customer.

Customer Acquisition

At the time that Velocity Black was sold, there were two different divisions of the company. The customer-facing product had a $2000 annual subscription fee as well as revenue-sharing on every request a customer would make. Those requests could be anything imaginable, but frequent requests included:

  • Booking a reservation at a very popular restaurant
  • Buying and delivering a special gift
  • Finding something exclusive to do at a particular destination
  • Booking private charters or difficult-to-find flights

Since Velocity Black controlled all payments, they would take those revenues upfront, which in addition to their annual subscriptions, made them a capital efficient business. 

The team didn’t sit on their laurels, however. They experienced 60-100% revenue growth year-on-year until acquisition and they reinvested most of that to keep growing the platform.

Where do you meet the sorts of customers who want to make a call and get something exclusive? At exclusive events, of course! Think of signature sporting events, like the F1 race in Monaco or the Super Bowl. They would always have a presence at the Oscars or Coachella. They would normally have a private event with some top tier talent performing which underlined the sort of exclusive experience they could offer their customers. In fact, when asked, customers often said that they used the service primarily to be able to deliver a special memory to friends and family.

Companies caught on to this as well, and there was also an enterprise division of the business that worked with large companies who wanted to ensure their employees felt special and looked after. This division was doing well and Alex knew it was simply a matter of time before a bank or credit card company came calling.

Closing the Deal

The acquisition by Capital One started as a partnership. Capital One wanted to launch a new credit card with some special features and they tapped Velocity Black as a partner to help them do that. That launch went well and Capital One asked if Velocity Black was looking for investment. Alex had already done a friends-and-family round as well as an additional seed round so the company was well-capitalized. He politely declined an investment. Capital One wasn’t deterred, and came back with a question about openness to acquisition.

Alex said he was open to it and went back to his co-founder and board, who were also open to exploring it. They hired a bank to manage the deal and accepted a second offer from Capital One which was around 10% higher than the original one.

Key Lessons

The story of Velocity Black offers some simple lessons for all businesses:

  • High tech + high touch: use technology to assist, not entirely replace, humans, particularly for elite customers that value a personal touch. Don’t be “too cool” to use AI and other such technology.
  • Go where your customers are: people who love great experiences are, unsurprisingly, at special places already having great experiences. When you take the time to create a customer avatar, you’ll know where the avatar hangs out. Go there.
  • Play it cool: when a big fish like Capital One comes calling, performing well in a partnership is precisely the sort of audition that leads to potential investment or purchase. See such partnerships for what they are and overdeliver when given a chance.

We can’t claim to be available 24/7/365 via an app, but we’re around during reasonable hours (even unreasonable ones, sometimes!) to help you with all you need for buying or selling a business. Give us a call today.

Case Study #77: A Hole-in-One 20 Years in the Making

Case Study #77: A Hole-in-One 20 Years in the MakingIf you ask Ian Fraser, co-founder of Tour Experience Golf (TXG) how he prepared to run his company, he would tell you that he spent 15-18 years being underpaid. He used that time to invest in himself and learn everything about his industry, golf club fitting, as well as the basics of business. It would pay off years later in a handsome exit.

Ian does have a Scottish accent, which doesn’t hurt in the world of golf, but he notes that while an accent may get you in the door, it’s the hard work and reputation that can keep you going. That reputation got him noticed by an investment group who made him an offer but it was clear that Ian’s ambition didn’t match the investors’ risk profile and Ian ended up partnering with a 50/50 partner with the caveat that until all the original investment had been paid back, the other partner could hold on to 30% of Ian’s 50% equity position.

Golf Club Fitting

If you’re not a golfer, you might not realize that there’s an entire universe of custom-fit golf clubs. Anyone who has experienced the difference between “off the shelf” clubs and custom ones will tell you that custom ones help you play better and enjoy the game more. Ian built a reputation for fitting and had people flying in from all over the world to work with him.

But he knew to build a business, he needed to scale himself. There were three tools he used to hire the right people:

  • Hire for EQ instead of IQ. Ian felt he could always teach the technical side of things, but being empathetic to the customer and his/her needs? That was something you wanted right away in a team member.
  • Choose the customer over the company. In the interview process Ian would offer scenarios in which the business, not the client, would win in a given scenario. Tied back to the point with EQ, Ian selected those who would choose the customer first. That was the ethos of TXG: serving customers first, profit comes as a result of that great service.
  • Consult in an open space. By using an open space instead of a closed room, Ian was able to have his trainees on either side of him, working with their own customers, and they could learn from and feed off each other on every consultation.


Another winning strategy Ian deployed was YouTube. The channel has well over 200,000 subscribers, and because Ian spent every Sunday and Monday filming for 2 years, including a Live Q&A every Monday, he built an online reputation and customer funnel that was unstoppable. While most people spend money on marketing, Ian was actually getting paid for his marketing, as it was responsible for $30,000 in revenue per month in addition to doing what great marketing is supposed to do: bring in clients.

Before too long, TXG was at $5M annually, with a waiting list of 1,500 to get in for a fitting.


The original acquisition offer wasn’t respectful for the sort of hard work Ian had put in and the acquirer implied that they were going into the marketplace “with or without” Ian but they discovered, as many had before, that you can’t just throw money at YouTube and you can’t just buy reputation. Ian had won in the video space because he had been consistent and the other better funded companies didn’t seem to include consistency in their channel rollouts.

As the acquirer realized it would be much harder to build what Ian had already done over so many years, they decided to buy that sweat instead of trying to do it themselves.


Ian intentionally built his business over many years. Three takeaways for those looking to exit well:

  • Duplicate yourself — by duplicating not just his technical knowledge, but his approach to customers, Ian was able to scale his company beyond his efforts.
  • Deliver content — Ian knew that YouTube rewards quality and consistency. He delivered both and got paid for his marketing efforts instead of having to spend for them.
  • Know your worth — when the acquirers tried to lowball TXG, Ian stood firm. As those acquirers started to get a better sense of the real value of the company, which would take a lot of time to duplicate, they realized their number was wrong.

We definitely have some golfers in the office, maybe even some with custom clubs! But even our non-golfing brokers can help you sell a business you’ve spent many years building. Give us a call.

Case Study #76: Veterinary Mini Roll-Up

Case Study #76: Veterinary Mini Roll-UpWhen Dr. Joseph Marchell started Old Brown Dog Veterinary Partners he was a broke, in-debt recent college graduate. But he took six months working at a private equity firm, observed what was going on in the marketplace, made moves, and bet big. In the end, he achieved a 28X EBITDA exit for the entity he helped to build.

Inefficient Markets

Joseph is the son of two veterinarian parents so he very much believes in helping animals, but he also has a real eye for business, and his first job out of school was not understudying with one of his parent’s practices, but rather working in private equity, helping to identify veterinary practices that could be bought and packed up into a larger entity with more value after operations had been streamlined and professionalized.

Indeed, because many vets are focused on animals and not spreadsheets, they end up functioning like solopreneurs and hence there are lots of inefficiencies that PE can improve, including that lowest-hanging of fruit, underpricing.

One More Leap of Faith

As Joseph continued to see skyrocketing values for veterinary practices he was evaluating for purchase at his PE firm, he brought his work home and had a conversation with his parents, talking about the value they currently had and how much more their business could be worth if it was part of a tactical roll-up. They were cautiously optimistic and before too long, Joseph created Old Brown Dog as the entity for this project.

While that entity was originally going to get funding to go out and get deals, Joseph had his hands full creating efficiencies with the three practices the entity acquired (his parents’ practices and another). Because he took the time to bring in a professional operations manager and someone fully in charge of HR, Old Brown Dog started seeing more profitability right away, leading to an even better possible multiple of EBITDA.

Further, Joseph was ultimately de-risking all these practices by putting people in place that reduced the key man burden on the practicing vet. Indeed, once all those functions had been hired, even the vet himself could leave and the practice could continue on with a new doctor. The mom-and-pop one-off practices were becoming part of a well-oiled machine.

22 NDAs, 8 LOIs

Joseph was working as a vet in these practices as well as working on the business so he knew he couldn’t also take it to market. At least…he realized that after he tried it first. When he realized he was in over his head he brought in an M&A advisor who took the business off the market and cut all lines of communication off with interested parties so that the adjustments to EBITDA were crystal clear and so that Old Brown Dog could craft the narrative for selling.

Once it went back out into the market, 22 NDAs led to 8 LOIs. Joseph took the three best and asked them to come back with their best and final offer. When the dust settled, he had sold the business for a value far beyond his parents’ wildest dreams, and right in the zone he had hoped for.

Key Lessons

This case study offers three helpful lessons:

  • Control the narrative: when asked why he was selling the business, Joseph was able to point to his limitations which were opportunities for a buyer, namely capital investment in buying other practices and hiring investment in getting HR and operations people in place as the roll-up continued. This allowed buyers to see where they could add value (and what that value could add up to). 
  • When the market moves, so should you: even though he had only been working in PE for six months, Joseph saw an opportunity for arbitrage and value creation by bringing efficiencies to what he had seen since his childhood: an inefficient market of veterinary practices. He didn’t wait to get more experience. He pounced, and was handsomely rewarded.
  • Savings are everywhere: even when you have an eye to sharpening pencils and cutting costs, there are always cost savings to be had. Even if you don’t plan a roll-up or plan to be part of one, there is a direct relationship between cost savings and the valuation of your business.

Considering a roll-up in your industry? We’ve helped others put those together before. Give us a call.

Case Study #75: Riding the Sports Gambling Wave

Case Study #75: Riding the Sports Gambling WaveWhen Kyle Scott started Philadelphia sports blog CrossingBroad in 2009 he was simply trying to stand out from the plethora of Philly websites by being a bit more edgy, willing to shatter some glass and ruffle some feathers. Eleven years later, due to some savvy business moves in a changing content environment, he enjoyed a cool eight figure exit.

Google Surveys and T-shirt Sales

As so many great business stories start, this one begins in a parents’ basement. Kyle had moved back home to try to make a go of being a content publisher and as he developed a loyal following due to the writing he put out each day, he looked for ways to monetize that audience.

Early on he used Google Consumer Surveys, which paid something for every user that would click through to answer some questions. This led to a significant bump in revenue for a while…until Google decided to keep those funds and direct them internally. Kyle learned a lesson about not being diversified in his income sources and added local events and t-shirts to the arsenal, eventually going viral with a Philly Special t-shirt that outlined a winning play the Eagles used in the Super Bowl.

The Supreme Court Changes the Game

In 2018 the Supreme Court struck down the federal ban on state authorization of sports betting in Murphy v. National Collegiate Athletic Association. This led to a number of states beginning the legislative process to legalize sports betting in the time-honored tradition of government grifting off legal gambling.

In his ongoing search to provide value while finding ways to monetize content, Kyle started to write “How Do I” articles on sports betting as it became legalized in certain states. Those articles would contain affiliate links from some of the sports betting companies that paid as much as $300 per user that would sign up, put in some money, and place a first bet. With hundreds of thousands of readers, Kyle saw the potential and went all-in on this strategy and when he saw $30,000 of revenue in one day he realized that this was a new vector for his company.

He added a business partner who had websites and a talent stack that offered good synergy and as other states were considering legalizing sports gambling, they came up with a strategy to acquire similar websites in those states before legislation took effect, as they had a game plan to then significantly increase the value of those properties.

Then Covid hit, and with money drying up for acquisition, they decided instead to partner with the websites they wanted to acquire in Colorado, Illinois, and the South. At the time of their acquisition they were doing topline revenue of $5M with SDE of $2-3M. 


Kyle had a respectable lifestyle business before the Supreme Court ruling. But because he saw the potential of what affiliating with sports betting websites could do to his business, he made a big bet and won. Here are three things Kyle taught us:

  • Build a loyal audience: Kyle says he was always focused on making his writing sound like he was writing an email to a friend rather than “optimizing for SEO.” While those don’t have to be mutually exclusive, Kyle’s hard work on the keyboard storytelling every morning won him an audience that was willing to fill out surveys and buy t-shirts to keep him afloat.
  • See where the puck is going: Wayne Gretzky famously talks about how he played to where the puck was going, not where it was. By seeing the popularity of sports betting grow from ground zero, Kyle and his team built a template that would add value and work state-by-state and got there before everyone else did.
  • Adapt: just as the Supreme Court launched a part of his business, Covid shut down his expansion plans. Instead of feeling sorry for himself, he adapted an acquisition plan and made it a partnership one, leading to growth that would see him get an enormous payday: $12.5M up front, $9.5M in a three-year earnout, and $3M of stock in the acquirer that would vest after a couple years.

We aren’t experts at sports betting, but we can better your odds of a great business transaction. Let us know how we can help.

Case Study #74: When the Market Changes, Pivot

Case Study #74: When the Market Changes, PivotWhen Jaclyn Johnson had a $40M all-cash deal for her events company, Create & Cultivate, implode at the 11th hour, she didn’t fall apart. She took the lessons she learned to get an 8-figure exit just a couple years later.

Side Project Becomes the Main Project

When Jaclyn created Create & Cultivate, she already had a marketing agency that kept her busy most of the time. What she was looking for was not in the marketplace: a community specifically for female entrepreneurs. It was a side project but also functioned as a development tool for her agency. The project wasn’t making money, but it wasn’t losing it either. Jaclyn partnered with corporate sponsors and charged a minimum fee in order to focus on building a community rather than an income stream.

When her agency was acquired by a strategic buyer, she was on the hook to consult with the new owners for a year, but in the meantime she also brought in a strategic co-founder for Create & Cultivate and together they decided to take this fun project and really go for it. Soon they were co-branding events with companies like Marriott (who were excited about bringing a lot of women to their newly redesigned properties). These events served as feeders for larger conferences run by the C&C team.

The Deal Blows Up

Jaclyn’s co-founder was going through a transaction for her own company and told Jaclyn it might be a good time to exit from C&C also. Everything was on track until signing day, when the deal fell apart. Keep in mind that Jaclyn had given up the lease on her office space and told senior team members about the sale. The big problem? Jaclyn was too involved in the day-to-day operations and hadn’t removed herself from the scaffolding. The buyers were (understandably) worried about what would happen if she disappeared. The $40M all-cash offer, which represented a strategic valuation of 20X EBITDA and which would make her the head of a publicly-traded company evaporated in an instant.


Jaclyn went right back to work. She built a C-suite, got ambitious about having a big exit (for real this time), and focused on recurring revenue, one of the most important value drivers of any business. In the case of C&C, that recurring revenue came in the form of a digital membership that gave access to gated content and members-only events.

The World Blows Up

Six days before an event at SXSW in Austin in 2020, the city holds a press conference to say the event will not be happening. At first Jaclyn was in denial. The cancellation of an event this late was going to represent a financial bloodbath for the company. As she was working through the process she was talking about scaling back events a few months out, but gearing back up for summer 2020. But her team members brought her to the new reality: those sorts of events weren’t coming back for a while, maybe even for years.

Just as she did with the failed first acquisition, Jaclyn got to work instead of feeling sorry for herself. In May 2020, she launched a digital event, with over 10,000 attendees who sent over 50,000 messages in the Slack for the event. By pivoting quickly to digital events, Jaclyn and her team helped lead the way in this relatively new space and by the end of the year the company was on the same EBITDA despite being on lower revenue.

Second Attempt at a Sale

Having been fortified with a blown-up deal and a formerly blown-up business model, Jaclyn was prepared to go to market again. She ended up with a $22M cash-heavy deal which bought out her partners completely and allowed her to roll a portion of her proceeds towards equity in the new company. She also took a portion of the proceeds in a performance-based earnout. Sure, it wasn’t the original offer she got years back, but a valuation only matters if a deal closes, and part of why that deal didn’t was because Jaclyn didn’t have the right value proposition in place. The next time around, she got 22 million validations for putting in the hard work.


Some great takeaways from Jaclyn’s story include:

  • Don’t mourn, pivot — instead of crying about the once-in-a-generation impact of Covid to an events company, Jaclyn went to another medium in the same business and capitalized on people’s hunger to continue to learn and connect despite lockdowns.
  • Built systems — when the seller is deeply involved in the day-to-day operations, it means the buyer is buying a job, not a business, and that’s a smaller buying pool with smaller numbers.
  • Be genuine and see what develops — all this came about because Jaclyn was interested in solving a genuine problem — more forums for female entrepreneurs to connect — and built a sturdy foundation for that. Because she did that work, it became easy to monetize it later on.

Are you concerned you’re a bit too involved in day-to-day operations to offer a credible sale to a buyer? We can help you change that narrative. Give us a call.

Case Study #73: Local Meat Delivery Peaks at the Right Time

Case Study #73: Local Meat Delivery Peaks at the Right TimeWhile most of us are now familiar with deliver-to-your-door monthly subscription boxes, in 2015-2016, this sector was only starting to heat up, and while prepared meal plans were well-known, businesses who focused on protein-only didn’t have that much competition. Enter Marc Lafleur and truLOCAL, which was acquired at the end of 2020 for an eight-figure sum. Not too shabby when you consider that Marc and his co-founder bootstrapped the business with $40,000 of their own money to start.

Path to Profitability

Apart from focusing just on delivering lamb, beef, and chicken, particularly from locally-sourced producers (the earliest versions of the labels had the names of the farms and ranches on them), Marc and his team knew that profitability lay in scaling the operations. Their first angel investment of $100,000 allowed them to hire their first two employees and they hit profitability midway through their fourth year in business.

Smart Advertising

Marc knew that the concept would take off if people could see it themselves and one interesting way he went about marketing was doing pop-ups at Crossfit gyms. They were able to show the quality of the meat and let members know they could sign up right there and get quality locally-sourced proteins delivered to their homes. This worked really well for them.

They also dodged the large-scale influencer marketing (think more than 20,000 followers) and followed the same method they used at the gyms: meeting people and sharing their stories. In fact, they targeted what is known as “micro influencers,” those with between 1000-20,000 followers who have a lot of credibility with their circles. This created a strong grassroots demand for the brand.

Dragons’ Den 

For those who might not be familiar with the show, Dragon’s Den is the Shark Tank equivalent in Canada (it even features shark Robert Herjavec). If you want to go down a rabbit hole, Dragon’s Den is an offshoot of an even earlier Japanese show! In any event, Marc only has good things to say about his experience, and not only because he ended up getting a deal with tech investor Michele Romanow.

He sees the preparation for appearing on the show as important personal development milestones. Even the selection of when you appear on the show is strategically important, and Marc decided to go on Day 1. Even though the entrepreneur before him came out crying, Marc wasn’t daunted, and was prepared for any questions the dragons might sling at him. He agreed to a deal on the show, and eight months later the funding came through.


By that time, however, Marc knew the company was getting to the right run-rate and growth for acquisition and he engaged an M&A firm to help him identify potential buyers. The first list totaled 420 candidates! The data room was up and running and Marc got engaged with the more serious candidates throughout the process.

One question that kept coming up was, “Are you going to stick around?” Marc, who saw himself as more of a builder, had no desire to stay on and stuck to the idea of a six-month transition, tops.

He also wanted to make sure his team was taken care of. He had always told his team that he wanted to be the lowest-paid employee in the company to help it grow, until the day of sale, when he would get his payday. His employees knew that he wanted to sell one day, but also knew that he had their backs.

In fact, of the three final candidates for sale, one company offered a significantly higher final offer, but one of the conditions was a virtual cleanout of the team. Marc turned down the money and went with one of the other buyers that would honor his pledge to his people and help them continue to grow their careers with truLOCAL.


Marc offers some good lessons for business owners in any industry:

  • Bootstrap whenever possible — by using he and his co-founders’ funds at the start, they were able to preserve more equity as they fundraised.
  • Don’t be boring with marketing — direct selling of your meat-delivery-service at gyms? Sounds strange at first…until you realize that those people, especially at Crossfit gyms, value high-quality meat and appreciate the community-oriented vision of buying local.
  • Treat your people right — by being clear on the company being acquired in the future, and telling them he would have their backs, Marc inspired his team to keep pushing forward, not just with him, but under the new ownership.

Want some ideas for marketing, digital and otherwise? We know some people who can help you. Give us a call.

Case Study #72: Cleaning Up in Style: Ron Holt’s Exit of Two Maids and a Mop

Case Study #72: Cleaning Up in Style: Ron Holt's Exit of Two Maids and a MopWhen Ron started Two Maids and a Mop (now Two Maids), he was focused on finding an industry that was broken but still presented an opportunity for a company to sustain itself and grow. Many years later, in part due to a chance conversation with Fred DeLuca of Subway fame and a random sighting of a yacht at Key West, he was able to get an exit he could be proud of.

Recurring Revenue

In the early 2000s an industry that looked broken to Ron was residential cleaning. He saw a fragmented landscape with lots of mom and pop operators and not a whole lot of efficiency. But he knew that if he could gain clients, he could latch onto a dream for many business owners, recurring revenue that over time can grow like compound interest. A $150 house cleaning in that frame isn’t one-off revenue, but one that can repeat twelve or in some cases 52 times a year.

Influenced by Seth Godin’s Purple Cow, which emphasized standing out among other businesses, Ron started with a business model that allowed people to pay based on how satisfied they were with the cleaning. As he told this story to potential customers, as well as his goal to spread this sort of satisfaction-based cleaning to other parts of the country, people listened and hired him. While some gamed the system, and Ron eventually transitioned to a standard pricing model, the “purple cow” method definitely helped him get traction early on.


Back in 2003, most people and businesses had no idea what SEO, Search Engine Optimization, was. It was possible to create content that was locally relevant and within days you would be ranking well within Google and other search engines. Since most businesses didn’t know about SEO, neither did cleaning companies, and this SEO strategy was key to getting Ron’s second and third stores up and running before he saw franchising as a way to grow the company, using areas with the least SEO presence as opportunities for the biggest land grabs.


While Ron wasn’t entirely thrilled with franchising, he did want to learn how to do it better, which landed him at a conference. He took a break during one of the sessions and met a man sitting outside who struck up a friendly conversation with him. Soon enough, he had introduced himself as Fred Deluca, whose Subway chain had 42,000 franchises at that time. Suffice it to say Fred learned more in that conversation than he did at the conference!

One of the lessons Fred shared with him later (they would go on to have more conversations in the months and years that followed) was the importance of balancing franchisee requests with company profitability. In essence, franchisees would often come with great ideas that would often help make their lives easier, but didn’t necessarily make them or the franchisor more money. Fred warned Ron against being bogged down in dealing with these ideas instead of the larger strategic work he could do running the company.


Thanks to Fred’s mentorship and hard work from his team, Two Maids and a Mop continued to grow, and by 2021 had 91 locations nationwide. Around this time Ron’s mother-in-law had a really negative experience with a moving company and as Ron searched around the Internet he found that her complaints correlated with those of many in different markets. As he googled around, he found that same excitement at the opportunity Two Maids and a Mop had offered him so long ago: a chance to make a difference (and a profit) in a broken industry. That original excitement for home cleaning had fallen into routine for him and he realized it was probably time to make an exit.

Around the same time he had taken a trip down to Key West and had seen a particularly beautiful yacht that had so interested him that he went down an Internet rabbit hole trying to find out its owner. It turned out to be owned by a company that bought businesses like Ron’s, those involved around home services. While he wanted to go hat in hand to try to offer Two Maids and a Mop as an acquisition to this company, his business broker (wisely) suggested he take it to market and allow other people a chance to buy it.

Home Franchise Concepts (the owner of the yacht) ended up being one of the three finalists looking to acquire Ron’s company and when one of the rivals for the bid gave Ron an amazing offer with a ticking clock, Ron went to Home Franchise Concepts and told them that he would rather sell to them, as they were more aligned with values and would likely treat the company the way he wanted it to be treated. Home Franchise Concepts did what they needed to in order to counter the offer and Ron ended up selling to them, not so he could rest on his laurels, but so that he could go on to found Pink Zebra Moving, paying homage to Seth Godin for the ideas he gave him so long ago.


Three key lessons Ron shared with us:

  1. Be willing to be a purple cow. Ron saw that there were many players in the home cleaning space and he wanted to differentiate himself. His unusual pricing strategy caught fire and allowed him to develop a customer base.
  2. Seek mentors. Ron’s attendance at a franchising conference allowed him to make a valuable connection that had a significant impact on how Two Maids and a Mop developed.
  3. Always take your business to market first. Even if you have a preferred buyer (and you end up selling to that preferred buyer), you’re never going to regret taking your business to market so that you can validate the value and create an atmosphere of demand and desirability.

Are you looking to create a purple cow effect in your own industry? We’d love to brainstorm with you on how to do that. Give us a call.