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.

Case Study #71: Web Design for Therapists

Case Study #71: Web Design for TherapistsThe saying “there are riches in niches” isn’t just a pleasant saying for Perry Rosenbloom. His recent 8-figure sale of Brighter Vision, a web development company focused just on therapists, is eloquent proof of it.

As is the case with many small businesses, Perry’s started with fixing one problem. His mother-in-law was a therapist and he helped her build a website. While he did so he got curious about the industry and found out that there was a big player in the space charging a fixed recurring charge each month for their services. With a little bit of hustle (and looking at the publicly available name servers) Perry found, effectively, their customer list, and started emailing those customers, asking if they would be willing to switch. That got Brighter Vision going.

The Covid Effect

January 2020 was Brighter Vision’s best month ever. They experienced 60-75% growth, and were starting to experiment with two different paths:

  • Selling more services to existing customers
  • Selling existing services to new customers, i.e. taking on another niche like dentists or chiropractors

The reasoning on the second point was that since all the systems were already in place to serve one niche, if there was clarity on customer acquisition cost (CAC), a new niche could be added seamlessly. The team was experimenting with Google AdWords to figure out CAC.

Then March 2020 hit. Churn started to skyrocket but Brighter Vision acted quickly, offering two months free to every customer. This stopped a lot of the churn and after two months in which therapists were at home, pondering how to grow their businesses, demand spiked.

A Software Upgrade

One of the pain points therapists shared with Perry was social media. They wanted to find better ways to market. After looking at the problem themselves, Brighter Vision concluded that software would be a scalable way to offer this service, but none existed. That’s when Perry went to his old boss, someone who had built and sold several businesses, for a $200,000 investment for around 8% of the company. The investment would be used almost entirely to build the software.

The software worked very well when it got up and running, but it took over a year to get to that point. Brighter Vision originally outsourced the build to a local firm, but after eight months of not only no progress, but software that seemed to get worse with each iteration, they turned over what they had to someone in-house to project manage and build it and a few months later, the software was complete.

Always Open

Perry received interest from acquirers prior to Covid and maintained an “I’ll always take a phone call” philosophy. He would give those interested their customer count, ARR, and growth rate. If they came back with something in the ballpark of what he was looking for, he would be willing to accept an LOI.

Having never sold a business before, Perry leaned on his investor as well as some wisdom from Chris Voss, via his book on negotiating. Both his investor and Voss drove home the idea of silence. Perry would even sometimes write down on a sheet of paper, “now shut up” to remind himself what to do after talking about a specific deal point.

Perry’s investor also helped set expectations by telling him that “all deals die twice.” Perry didn’t go into any of the conversations or negotiations with potential acquirers with any emotion. He accepted that they would make their case, but as noted above, he often chose silence as a part of his negotiating.


Three takeaways from this happy ending for Perry and his team:

  • Trust your gut. During the software build process, there were numerous red flags that indicated that the company they hired to build the software were completely lost in the sauce. Perry feels he should have made a decision sooner to dump them and cost his company eight months of time because of not trusting his gut.
  • Silence is golden. Negotiation isn’t just silence, but silence is a big part of negotiation. This doesn’t mean that you should just ignore questions or counteroffers! But it means you can continue to reframe your position in numerous ways the same way. However, ghosting is not a strategy (especially with your advisors!).
  • Master a niche, then consider other niches. If you have already mastered a niche, consider adding another niche that makes sense. You’ve already done the work to cater to one type of customer, if another niche is close enough, you can bring your team more work, another level of expertise, and the company a whole new stream of revenue.

Feel like you will need help negotiating your business sale but don’t have an investor like Perry did? We can be there for you. Give us a call today.

Case Study #70: Read the Fine Print

Case Study #70: Read the Fine PrintJason Bagley sold his South-African-based cold email lead generation company, Firing Squad, to an American marketing agency but lived to regret the deal when he realized that the contract he signed didn’t give him what he expected.

Cold Emails

Most people don’t like writing cold emails. They know that it can work, but the stress and pain involved in writing them is enough to discourage them from pursuing it.

That’s where Jason and his team came in. Originally oriented as a web design firm, Firing Squad simply didn’t have enough recurring revenue and to dig them out of this hole Jason looked at his top recurring client and saw that it was an email newsletter business. He decided to pursue emails a bit more narrowly and almost in prophecy, wrote a number of cold emails to offer businesses help with a cold email service.

“How do we know this is going to work?” Many of the business owners unironically asked Jason when they had their appointment.

“You’re sitting here based on a cold email, right?”

Fair enough.

Secret Sauce

Jason was the top writer of these cold emails, but he knew that he had to pass on his knowledge to team members in order to scale. He did this through Looms or live video chats in which he would explain why something needed to be changed. An example he shared of a change he would frequently push was closing with a question.

Emails might end with “Let’s have a chat.”

“That’s not a question leading to action,” opines Jason. Go for a close, like “Can we chat?”

Little tweaks like these led to better success rates for his emails.

Apart from writing, Firing Squad’s secret sauce included how many emails to send and who should be targeted.

Challenges and Scaling

While Jason and his team were experiencing success, they still felt like they were on the same revenue treadmill that they were on when solely working on web design.

In the best cases, they created so much new business that the companies that hired them turned off the service because they couldn’t handle any more new leads.

In the worst cases, they only were able to get a few leads for the clients, making it not worth the client’s money or the team’s time.

Jason thought expanding into the US market might help him find a balance between these two types of clients and started having conversations with US-based businesses around referral partnerships. One of those conversations took a turn towards acquisition.

Jason knew that given how much he was still involved in writing the emails, he didn’t really have a business to sell as much as he could offer himself as a kind of acquisition. 

Looking for Upside

So Jason offered Firing Squad lock, stock, and barrel, in exchange for some base pay and some equity in the acquirer. After some negotiations, they agreed, but one of the deal points included significant price increases for the South-African-based clients. By significant, that meant tripling the prices.

Jason played the “we got acquired and the acquirer has forced us to do this” and after some grousing, a lot of the existing clients came along — which also offered an unexpected insight into how underpriced those services had been.

Jason was fine with working for the acquirer as long as he knew that at some point when he chose to leave he would be able to cash out what he had helped grow. Except that’s not the deal he signed.

Read the Fine Print

Jason had wanted actual equity, not shadow equity that evaporated when he left the company. The problem is that he got the latter and his lawyer hadn’t told him that he hadn’t received the former because he never clearly explained what he wanted to his lawyer.

Worse, the agreement was subject to US laws and Jason didn’t want to fly to the US to fight a court case. He chalked up the mistake to inexperience — avoidable inexperience — and went on to found another company.


Three key takeaways here:

  1. Clearly communicate with your lawyer. He/she is paid to review paperwork, but can only offer you good advice if you are crystal clear on the outcome you want.
  2. End prospecting emails with a clear question with a bias towards action, rather than a lukewarm suggestion.
  3. Recurring revenue is king

Need someone to help you read the fine print? We know good lawyers who can help. Give us a call.

Case Study #69: Know When It’s Time to Go

Case Study #68: Know When It's Time to GoSaaS businesses have developed a reputation in recent years for being all about the numbers as well as a relentless drive forward. Natalie Nagele and her team at Postmark had been in SaaS for many years and she went the other way, establishing a four day work week and confessed that before getting the business metrics in place for acquisition, she couldn’t tell you customer LTV. That didn’t stop her from getting acquired for a life-changing amount of money by Active Campaign earlier this year.

Built for Speed 

Ever had to reset a password? Or got a notice to retrieve an abandoned online shopping cart? Or clicked on a button that allowed you to send a link from a website or app to someone’s email? That’s transactional email, and most people don’t realize there are services operating that help deliver those emails.

Put another way, a transactional email contains information about an action the recipient has already taken. Broadcast email usually wants to nudge the recipient into taking an action. Particularly in the case of a sale, you want those transactional emails to go out as soon as possible, and Postmark built its reputation on speed.

When Is It a Bad Day vs When Is It Time to Sell?

All business owners have experienced a bad day or a bad week or a bad month. You could lose a key employee, have had to fire a bad one, or just not hit your numbers. You pick yourself up, dust yourself off, and handle what needs to be done. Sometimes you even feel refreshed and rejuvenated when you work through those challenges.

Natalie says that the dividing line between those regular ups and downs and a signal it’s time to sell is the thought, “I can’t do this anymore.” She was nearing that point before the pandemic hit, which temporarily put everything on hold as she focused on making sure the company — and all its team members — were fine. 

She also found herself often dreaming of hotels (a future business venture) which she knew meant that her focus and energy weren’t being put in the company, which wasn’t fair to her team.

But once things stabilized she and her husband (also her business partner in the company) realized that it really was time to let go, and that if she stayed and the team could see that they didn’t really want to be there anymore, that the company would be harmed. The 22 years they had spent building the company came to a happy conclusion when, unsolicited, Active Campaign reached out to see if there could be a deal, and after outlining her “must-haves” to the Active Campaign team, all else in the transaction went smoothly.

Natalie’s Must-Haves

Natalie had quite a few conditions as part of the sale, but the three that really mattered to her were:

  1. No working for the new company. She felt like she had the income she wanted and as we noted above already, after she took time off she wanted to look at a hotel venture. She was happy to have a brief transition period but after that she wanted to head off to retirement.
  2. Four day work week had to be preserved. This was an important step Postmark had taken years earlier and she felt that her employees had built their lives around it and didn’t want a sudden disruption.
  3. Bonus plan. The employees were used to a regular bonus that was tied to performance and she wanted to make sure, at least in the first 12 months, that this was honored. She ended up doubling down on this by sharing 10% of the proceeds of the sale with the team, some of whom also received life-changing amounts of money.

If you’re feeling like it’s finally time to let someone else take your business to the next level, we’d love to help you! Give us a call.

Case Study #68: E-Learning Cash Out

Case Study #67: E-Learning Cash OutWhen Mike Winnet quit his job to start a new business, he really didn’t know what field he would be going into. He started searching for jobs and noticed that 90% of them were asking for effective time management, clear communication, and great team work. But there weren’t certifications for these skills. He thought about what he would do if he was looking to acquire a particular skill: look on YouTube. When he started to research the e-learning space he wasn’t too impressed. So, E-Learning Heroes was born.

Taking Down Your Own Industry

If you ask Mike about what was wrong with e-learning when he started building his company, he won’t be shy. He said that the big players were creating courses that were:

  • Too long 
  • Too boring
  • Designed by nerds for nerds
  • Expensive

Worse, a lot of these companies pitched e-learning as a be-all and end-all. But Mike and his partners disagreed. Real learning is experience, in the field, shadowing, etc. What e-learning could do very well is prepare people for experience or recap experiences. It could not possibly substitute for experience.

So not only did E-Learning Heroes seek to counter all these problems, they also engaged in digital marketing that actively made fun of these issues, leading with videos like “Here’s what’s wrong with e-learning.” Understandably, these videos got a lot of attention from potential customers and a lot of bad will with competitors, though they would eventually come around in their own way.

So, E-Learning made their videos:

  • Shorter. Instead of 1-2 hours, a “course” could easily be 5-6 minutes
  • Interesting. Instead of trying to cover a lot, often a course focused on 1-2 things.
  • Fun to watch. Instead of having nerds in a lab come up with courses, they really looked for compelling instructors.
  • Inexpensive. Instead of selling “per head,” which Mike reasoned would punish companies for growing, he charged per course.

In addition, he didn’t make companies sign lengthy contracts that were difficult to get rid of. His cheaper pricing also allowed companies that were unhappy with their current solutions to give E-Learning Heroes a “test drive” while finishing up an existing contract and that test drive often resulted in a company switching over to E-Learning Heroes completely when their contract was complete.

Being Intentional

Before Mike sold, he was doing $140k in Monthly Recurring Revenue (MRR) and an annual profit of $400,000. He didn’t have a particular passion for e-learning (he had just seen a hole in the marketplace), he didn’t want to create an ongoing brand in the e-learning space (he was happy to let others do that), and most importantly, he felt that if he was able to build such a business with no experience and no real financial resources, it would only be a matter of time before one of the big players came in. So, he was always open to an acquisition.

Turns out it would come from one of the partners that E-Learning Heroes developed along the way. As part of his intentionality, Mike made sure his courses were compatible with the platforms of existing big players so that a potential future acquisition would be easier. When partners demanded exclusivity Mike would always give the same answer: “Buy us.” It turns out that some of those partners did take him seriously and he ended up selling. The company eventually sold for roughly $10M just under three years from when Mike started it.

And those competitors that Mike made fun of in the early days? They changed their pricing and course models to emulate the path E-Learning Heroes paved.


Mike’s got such an awesome story: he helps remind us that there are businesses and ideas just waiting to be created. Here are three takeaways:

  1. When Mike first packaged his courses, he was aiming at job-seekers. He thought these skills would help them land jobs. Priced at around $50, he managed to sell zero. But when he took the exact same courses and pitched them to HR professionals and other similar decision-makers at companies, he sold 340…at $10,000 each. He had the right product, but was pitching the wrong people at the wrong price. Pivot and win.
  2. Mike loves guerilla marketing and one of the ways he got the attention of some of the top companies in the UK (where E-Learning Heroes was based) was sending a personalized animated video to each of them. Because it was such an unusual approach, and because he had taken the time to do something fun, Mike got a 50% close rate on this initial outreach.
  3. Another aspect of guerilla marketing was Mike’s time efficiency (he was living his courses!). He would make a list of the questions he was answering in sales calls and then do videos answering those questions. He’d then post them on LinkedIn and other relevant platforms. He did what so many business owners dream of doing but fail to do: multiply themselves.

We don’t have any e-learning courses for you yet, but will a podcast do? Check them out here.

Case Study #67: Cashing In By Helping Small Landlords

Case Study #66: Cashing In By Helping Small LandlordsMost landlords who own fewer than ten properties use pen, paper, and spreadsheets to manage their tenants. But in a digital age, aided by solid software, there had to be a better way. Or, so thought Ryan Coon, who built Avail and enjoyed an 8-figure exit to His story offers lessons for all business owners, even if they aren’t building a software company.

Freemium Model

Most people are familiar with the freemium software model, in which some basic features are offered and the more advanced ones are offered to those who are “power users.” Popular examples include Spotify and Dropbox. 90% of Avail’s users are on their free tier, and they often remark, “I can’t believe this is free.”

But it took a while to figure out the right balance of paid and free features. The team played with different landing pages for their Google ads and found that often customers were happy to pay a little something for software that met their needs. They often valued that payment more than software that was entirely free.

This led to discovering that their average customer LTV was $500, which happened over a four-year period. But since they were spending up to $100 for customer acquisition, that meant that they needed to get outside funding to fuel growth to gobble up market share. That meant they couldn’t bootstrap and so Ryan had to spend portions of his time on the road meeting potential investors.

Keep It Simple

A key part of branding your business is not making the business name difficult for your customers. While Ryan and his business partner thought that “Rentalution,” a combination of “Rental” and “Solution.”

Good theory. But reality refuted that theory daily.

Ryan’s desk was near customer service and on a daily basis he overheard his reps gently correcting callers who clearly spelled the company name wrong. Hilariously, when he announced the name change to investors, one said that he liked what he thought was the current name of the company…and went on to spell it incorrectly.

Point taken all around, and Rentalution went away and Avail emerged.

Ryan noted too that Avail was about helping both landlords and tenants whereas the old name sounded like a detached software brand.

Getting Acquired

Given that they raised their last round of funding only six months before the company sold, even the most casual observer can see that selling the company was not on Ryan’s mind. What happened, however, was a series of conversations that led to “let’s explore” with a financial services firm who thought that a curated list of landlords would be a good fit for some of the other products they were offering.

But the kickoff call revealed that this probably wasn’t going to be a good cultural fit. At the time Avail had 45 total employees and the would-be acquirers had 50 on the call, of whom 40 were lawyers!

But the Avail team didn’t want to give up immediately and made it pretty far down the road with them before both parties decided not to move forward. 

But that meant that they had a data room full of reports and that helped accelerate the process with who would be the eventual acquirer,

Lessons Learned

Three key lessons from this story:

  1. Branding — while functional brand names make sense, brand names should ultimately be easy to spell and remember. Make sure that your brand passes the “simple” test by asking people to repeat and spell your brand. 
  2. Know Your Numbers — if you don’t know your customer LTV (lifetime value) and CAC (customer acquisition cost) there’s no way for you to find out whether your marketing is making you any money or even how much you should be spending on marketing. Make it a priority to know these metrics asap if you don’t already.
  3. Cultural Fit Matters in a Transaction — while it isn’t the first thing that might occur to sellers, buyers should be a cultural fit for your organization, or an implosion might happen shortly after the sale. While Ryan and his team didn’t stop the transaction when he felt uneasy about a cultural mismatch, he did note later that he was better informed for future business transactions. Don’t be afraid to walk away from buyers who are not good cultural fits.

Looking for a business in the real estate sector? We have those! Give us a call today.

Case Study #66: Aging a Wine Bar for Sale

Aging a Wine Bar for SaleRunning a wine bar may sound like an amazing lifestyle business, but like any business, one day may be the right one to move on to other things. That happened around the 50th birthday of one of the owners of The Art of Wine in Sedona, Arizona and the sale of the business offers some helpful lessons for buyers and sellers.

A Winding Path

So few business owners will tell you that they knew they wanted to own such-a-such business “when they grew up.” So often winding career paths make them experts in fields they might not know existed before landing on something they loved, were passionate about, or were really good at.

Laura Gisborne, one of the owners of The Art of Wine, took one of these paths. She married into a family business in her early twenties, exited after a period of time with her husband and got into real estate, which exposed them to retail businesses, which they also ventured into. During this time they moved to Sedona, Arizona, where they decided to open a wine bar to cater to the 3-4 million annual tourists that Sedona sees.

This would be the 9th business that Laura was involved with.

Runaway Success

The business took off and before too long they had added a wine subscription business to their events and tastings. They shipped a box once a quarter and made an effort to curate the box around the tasting preferences of subscribers instead of just using it as a place to dump overstock or clearance inventory.

The quarterly shipments depended on a year-long original commitment, after which time they often saw churn around 30%, but since they had a solid stream of new subscribers through their retail location, that core continued to build up.

Laura’s first job was at McDonald’s and she very much took to heart the lesson of creating written manuals that would enable people of high school age and intelligence to run key business functions. While high schoolers obviously couldn’t help with a wine bar, she kept the same principles in place and advocates for every single role in a business to be clearly articulated in written form. It’s short-term “pain” with lasting value.

She believes that everyone in the business has to be replaceable, not just for running a business, but for eventually selling it, something she always considers when creating a new venture.

“It’s Time”

Often the end can come suddenly. A business owner can wake up one day and realize he/she is mentally done and needs to sell. Less ideally, people can go through a personal crisis and be forced to sell. In this particular case it was more of the former: Laura’s husband hit his 50th birthday and realized he didn’t want to work at a wine bar anymore, even at the 15-20 hours a week he was working.

For her part, Laura had started to get more speaking requests around entrepreneurship and leadership and realized she would like an exit that would allow her to pursue that as well.

After experience selling more than half a dozen businesses, they opted to list the business on BizBuySell and had three different serious interactions in which she required not just an NDA but the unusual additional requirement of a noncompete, as the market in Sedona had significantly changed since they were the first mover in the space back in 2005.

Last Call

One of the potential buyers made it far enough into the process for a site visit, and Laura and her husband discovered that there was a lifestyle motivation as well: the couple looking to purchase lived in Washington State, with hundreds of rain days a year, and were looking to move to sunny Arizona anyway.

The Art of Wine had been sliced up into different business lines, primarily to give Laura a bit of negotiating. She knew the inventory would be worthless to them once they sold, so she held it as a bargaining chip should they need to push the deal over the line (they could “throw in” the inventory).

However, they discovered that the nonexistent regulation when the company was started in 2005 had developed at the same pace as the burgeoning Arizona wine industry. That meant the new owners would need a liquor license, something Laura and her husband never needed because they were grandfathered in.

That meant telling the buyers that they needed to spend $20k to acquire a license before the sale closed. For their part, Laura and her husband simply deducted that $20,000 from the selling price to make sure they were offering a like-for-like scenario: the business would have been on a completely different footing if they couldn’t serve wine at events.

Thankfully all went well and The Art of Wine was successfully handed off to new owners grateful to change their climate in addition to their income stream.


As always, there are lots of lessons here, but we will focus on three:

  1. What might new owners need? When they went to sell, they found out a buyer would need a liquor license and thankfully there was one available for sale, but if there hadn’t been, the deal would have been substantially altered or possibly dead in the water. Keep track of changes that you personally might not need to be compliant with but a buyer would. 
  2. Add a subscription line of revenue. While subscription businesses are second-nature now, they weren’t when The Art of Wine first got started. How might you add on subscription revenue to your existing business or one you are looking to acquire?
  3. Don’t wait. When you are “done” with a business, your team members will notice soon enough. Don’t wait to put an action plan in motion…a plan that you come up with long before you find you’re “done.”

Want to buy a wine bar or some other hospitality business? We’ve got options for you. Call us!

Case Study #65: Smoke ’em While You Can

Case Study #64: Smoke 'em While You CanIn 2015, Lorenzo de Plano and three other business partners started a business in the janitor’s closet of a Los Angeles parking garage. By late 2018 their business was doing $1-2M a month in topline revenue with a 40% margin. Not long after that, they exited for a cool $15M. Their business? Solace Vapor, which “specializes in the production, manufacturing, and distribution of unique nicotine supplements to replace conventional combustible cigarette usage.” Lorenzo helped build a vaping company.

Bootstrapped in a Wild West Marketplace

Vaping was already well underway by 2015, so Solace wasn’t trying to take over the marketplace. Instead, they took advantage of the research already done by Big Tobacco, which had filed numerous patents over the years around adjusting the pH levels of tobacco. By focusing on adjusting the pH levels of the liquid (often referred to as “juice” in the vaping community) as well as the size of the cartridge, Solace focused on serving a particular niche of the vaping market.

This community was 35 and older and weren’t interested in making the big, obnoxious smoke clouds delivered by the large devices. They wanted something smaller and discreet. Less of a “statement” and more something to enjoy. They took their ideas to the manufacturers to help create smaller devices and they had a couple takers.

Their first year they burned through all their cash (they each put in $5k) and went into credit card debt. But before too long they were off to the races.

When the government doesn’t regulate something, it’s often a “wild west” scenario, and to some extent, the vaping/e-cigarette market in the United States still is. This is due to the fact that many saw this as a gold rush of sorts and hence did not file paperwork with the FDA, thinking that when it came time for regulation they would just shut down and declare bankruptcy. In the meantime, they planned to “smoke ‘em while they could,” and make as much as possible.

Those who took the time to actually put together applications with the FDA ended up with the most severe financial penalties (that story, and thoughts on why those who try to follow the rules get punished, are for another time).

Regulatory Event

Just as insurance providers prepared for the regulatory event of what was then called Obamacare, those in the e-cigarette and vaping space were considering their next moves as it became clear that there would be some regulatory action from the federal government.

Lorenzo and his partners (now just three, as they had already bought one out some time before) knew that this regulatory event would compress the company’s valuation, but they thought their venture would make more sense inside the portfolio of a larger company that had the pockets and the stomach for a regulatory fight.

They took the business to market and engaged with four serious buyers, got LOIs from three, and went the full way on due diligence with two of them.

They ended up taking the slightly lower offer that gave them a chance to grow within the structure of another company rather than simply being paid off and dismissed. In this case, only three years into the business, they weren’t sick of something they wanted to get rid of, they simply wanted help, and wanted to take some money off the table in the process.

The payday? $15.25M, $8.25M which was upfront in cash, with the rest in restricted stock. They had to divest or sunset any assets of the business that dealt with cannabis or CBD as the acquiring company did not want to have that part of the business.


Lorenzo’s story from startup to sale is not a long one, but it’s full of helpful lessons:

  • Be flexible about partnership. As we noted, the company started with each founder taking 25% and giving equal amounts of capital to start the business, but they agreed that those percentages could change based on life events or changes in who was contributing what. Because they had worked out a way to value the business, when it came time to buy out a partner who had to move on with some other personal needs in his life, the transaction was seamless.
  • Be clear on the type of exit you want. Lorenzo turned down a higher offer because he didn’t want a “walk away” transaction. He was hungry to keep building the business, but he wanted to do it with help, so he took an offer that was lower at the outset, but with the chance to grow the business, could end up being a much more lucrative one in the long-term.
  • Think well on regulatory events. Lorenzo saw this problem coming in 2018, but the federal government, slow as it was, didn’t start making big moves until years later, with some of their biggest moves, removing JUUL e-cigarettes from the US market, didn’t come until 2022. Don’t wait for regulation to happen to your business. Be proactive and engage with someone who has a vision for what to do within the context of future regulation.

While we may not have a vaping business to sell you, we do have plenty of other smoking-hot deals here at Apex. Give us a call and we can share them with you!