We’ve shared many paths to product-market fit here on The Review that are chock-full of lessons for aspiring tech founders. But perhaps none we’ve shared to date are as deserving of a screenplay quite like Adam Guild’s.
When Guild was just 12 years old, he built a Minecraft server that ballooned into a six-figure business with millions of players worldwide. He enlisted his 10-year-old brother to run its Instagram meme page for just $5 a month (which quickly racked up millions of views). By age 16, his Minecraft community was so successful that he decided to drop out of 10th grade to keep scaling it.
Entrepreneurship was a family business. Around the same time, Guild’s mom pursued her dream and opened a dog grooming salon in West Hollywood. But finding customers proved challenging, and she worried she’d have to give up the family house she’d taken out a loan against to fund the business. At just 17 years old, Guild jumped in to help her increase bookings with local search optimization. The seed for Owner was planted.
But plenty of challenges cropped up along the way. His young age (and self-described baby face) made it hard to be taken seriously by potential customers. He hustled on cold sales outreach and got a response rate south of 1%. And even after finally building some traction for a fully bootstrapped platform that drove reservations and dine-in for restaurant owners, all the company’s revenue evaporated when the pandemic broke out in March 2020.
As Guild tells it, the nonstop grind and misfortune of the company’s early years paved the way for Owner today, now a billion-dollar platform powering the growth of thousands of restaurants across the country (which recently nabbed a Series C fundraise). He did it all with hardly any credentials or network — by the age of 25.
While Guild’s story is fascinating in its own right, his path is full of lessons for any entrepreneur with a nontraditional background. Let’s dive in.
Helping his mom’s business sparks an idea
When Guild dropped out of high school halfway through sophomore year back in 2017, he was a full-time gaming entrepreneur. There were parts of it he loved — he got to learn software engineering and growth marketing in practice. He’d become financially independent as a teenager. He was having a lot of fun.
But he started to feel conflicted about staying in the gaming world. As he saw it, the more he scaled his gaming community, the larger his “negative impact.” “I was obsessed with getting millions more players to ultimately waste time on my games so that I could make money,” he says.
He didn’t see a clear alternative path. “I felt trapped. I didn't have a plan B. I was a 10th grade high school dropout. I knew there had to be some way to use the skillset I built to actually help people,” he says.
At the same time, his mom was getting her dog grooming business off the ground — which she’d spent years saving up for while raising Guild and his brother as a single mom. But her excitement quickly turned into worry as she was unable to increase revenue. She struggled to build a consistent customer base and wasted money on expensive, big-tech solutions that promised growth (but didn’t deliver).
With a hazy career plan of his own, Guild jumped in to help his mom. “I saw her in this really terrified place. We talked about it one night, and she asked for my help in figuring out how she could grow this thing,” he says. “But I was worried that I wouldn't know how to grow a physical brick-and-mortar business because it felt so different from gaming.”
He started by putting his Minecraft growth playbook to the test and built an Instagram page for the dog grooming salon. But even after growing her follower count with some viral posts, he quickly learned that social media marketing wasn’t effective for a local business. Virality is global in nature — one million views didn’t translate to West Hollywood walk-ins. And folks don’t generally browse social media with the intent to buy.
Guild then experimented with other growth tactics, from direct mail to receipt ads, but nothing clicked — until SEO. “It worked like crazy,” he said. “Even though SEO generally takes time to be effective, that’s only for terms like ‘best shoes’ that are globally competitive. I discovered no one was optimized for specific and local longtail keywords, like ‘dog grooming West Hollywood’ — which received hundreds of queries every month with the intent to buy.”
With a quick-and-dirty SEO revamp, his mom’s business went from struggling to crushing it over the next year, bringing in heaps of customers who discovered her shop on Google.
Guild wanted to replicate the fulfillment he felt from helping her in his next entrepreneurial endeavor. “When I saw my work finally have such a positive impact on my mom, not only financially but personally, I was inspired to build a business that could do the same for as many people as possible,” he says.
The V1 product: A forked WordPress for small business owners
In the process of helping his mom’s business, Guild cobbled together the first prototype of Owner. It was a super opinionated, forked version of WordPress — a website builder with little room for modification that handled all the technical SEO best practices. He says this rigid design was based on one contrarian insight he’d learned from remodeling her website: Software customizability is actually counterproductive for SMB customers.
“At the time, most small business software had been built with the assumption that customizability is king. Small business owners can use a tool like Wix and choose from thousands of templates and then add their own site copy,” he says. “But what I noticed when helping my mom, and what I’d observed from a lot of other local businesses' websites, was that they make mistake after mistake, like not adding alt text to images or not including the right keywords in meta titles. So I wanted to build an out-of-the-box system so users would have everything they needed to rank at the top of Google.”
He planned to launch the business the only way he knew how at 17 years old: entirely bootstrapped. And the way to do that was to become profitable. So he landed on a premium pricing strategy.
“At first, we were charging $2,000 per month as a website builder that drives dine-in and reservations. To put that into perspective, the typical website builders small business owners use are Wix and Squarespace, and they cost $49 per month. So we were 20X the price,” says Guild. “To command that price, I thought to myself, we have to deliver an ROI that is commensurate with the cost.”
A high price ends up being a great forcing function for developing an excellent product. You have to focus on whether it delivers a good ROI.
Finding customers through brute force
To figure out which kinds of small business owners to sell to, Guild began by literally knocking on doors. He pulled up to small businesses all across his native Los Angeles, from hair salons to laundromats, to talk to owners about how they were doing SEO.
Among the many difficulties of door-to-door sales, Guild faced one specific challenge: No one would take him seriously. “I wasn’t just 17 years old — I was a teenager with a baby face. I looked like I was in middle school,” he says. He even tried going to conferences to strike up conversations with owners organically, but he was mostly shut down.
Guild tried cold outbound as well, hoping his baby face wouldn’t thwart his response rate online. “I sent hundreds, if not thousands, of cold emails,” he says. He even tried, in his words, “doxing” folks — finding cell phone numbers online with background check tools. But most of those emails and texts went unanswered.
Eventually, his volume-shooter approach yielded a few meaningful conversations within one large group of small businesses: restaurant owners. He walked away with a key insight — driving reservations and dining in is the only thing restaurant owners care about. “Everyone told me, ‘Online ordering sucks for us. We lose 30% of every order to delivery apps. We lose all of our customer relationships on those platforms. If you're going to build something, help us drive dine-in and reservations.’ And I took them literally and focused on building a product to do just that.”
So he narrowed his efforts to restaurant owners, and finally, his success rebuilding his mom’s website helped land him his first customer. “I had emailed Morten Kaag, the owner of Tortilla Republic in West Hollywood, seven times. Then I’d cold texted him, and he was intrigued enough to take the meeting. I demoed what I did for my mom, and he was naturally very skeptical,” says Guild. “Then he asked, ‘What’s your mom’s dog grooming business called?’ I told him, and he said, ‘Oh, that’s where we take our dogs.’ And I said, ‘How’d you hear about it?’ And he said, ‘Google.’ So I said, ‘We’ll do the same for your restaurant.’”
Kaag was iffy about the $2,000 monthly price tag, but agreed to try the product if within 90 days, Guild could meaningfully lift the restaurant’s sales. And sure enough, 90 days later, Tortilla Republic’s sales jumped more than $10,000 per month. Kaag owned another restaurant, so he asked Guild to help with that one as well. With that, Owner had its first two paying customers.
Guild kept hammering on cold outbound over the next year to continue growing the customer base. Even with a few happy customers as proof points, it was still a slog.
But in retrospect, he says there was a dual advantage to building up his founder-led sales muscle — it validated the original product’s high price point. “A sales-led motion forces you to talk to customers extensively at every step of their journey, and it creates a higher perceived value of whatever you're selling,” he says. “Product-led models have basically free products because they don't offer the same level of perceived value or trust on the front end.”
When we were bootstrapped, we had to command a high price point to be profitable. So it helped to have me as a founder personally explaining how the product works, because then people were willing to pay more.
As the product made its way into the hands of more customers, Guild points to two reasons the first version was so successful:
- The utilitarian component: Is the product doing what it’s supposed to do? How much sales is it driving?
- The emotional component: How does using the product make you feel? Does it help you become an aspirational version of yourself?
Guild’s advice here is not to discount the emotional component when building your product. “I think most people assume the utilitarian part is more than 90% of the equation. But I’d argue that it's at least 50% emotional, if not more,” says Guild. “Customers want to feel smart and ahead of the curve with software, and that’s especially true for small business owners who are outside of the tech world.”
It wasn’t just the product itself that made Owner’s customers feel like they were on the cutting edge — Guild served as a dual founder-customer success manager that first year. “I’d do monthly progress calls with the restaurant’s entire team, which made them feel like they were getting state-of-the-art technology and service. And they felt smart for making the decision to trust us and use our product.”
Drumming up inbound demand through content
Eventually, Guild had hit his breaking point with his cold selling. “I didn’t want to scale a business through outbound because it was so brutally hard. I basically had to spam people to get them to take my meeting. So I wanted to develop a model where they would instead come to me,” he says.
He began to think about what a content marketing strategy might look like for Owner, starting by writing blog posts about how to grow a restaurant online. But he soon realized he needed to work on building his authority as someone who had no credentials in the industry. He had an idea to contribute to restaurant-specific publications.
Leaning on his cold outreach approach once again, Guild emailed editors of all the top restaurant trade magazines. He heard nothing back until the editor of Modern Restaurant Magazine offered him a guest post opportunity — as long as it was good. Guild researched extensively to draft an article about online marketing best practices for restaurants, which made it into both the print and online edition. The online version went viral, becoming the magazine’s number one story of that year.
Guild’s viral guest post helped him secure recurring contributor positions at several other publications, in addition to writing for his blog, which created a content flywheel. He says this process of content creation had a knock-on benefit: He’d become even more knowledgeable about his industry. “The work I was doing to research these articles improved my ability to communicate with the restaurant community, and gave me a much deeper understanding of the broader landscape,” he says.
By late 2019, the gears of the distribution engine were turning. Owner had a roster of a few dozen paying customers, and several strong leads had come directly from the article Guild had written. He had successfully bootstrapped the company to six figures in ARR. And the company had just landed its biggest fish yet: P.F. Chang’s. They closed a contract that had the potential to bring in $1M per year if the restaurant chain rolled the product out to its hundreds of locations. Then March 2020 hit.
The pandemic pivot
Owner’s progress ground to a halt. The whole product had been optimized around dining in. “We lost product-market fit overnight,” says Guild. “And we lost all the customers that we’d just spent two and a half years grinding like crazy to acquire. As a bootstrapped company, that was our funding, so we had to go back down to a skeleton crew of just me and one other person. We had four months of cash left to figure something out. I even thought I’d have to move back in with my mom.”
So he got on the phone with customers. “I asked them, ‘What do you need to be successful in this time?’ And they practically screamed into the phone telling me what they’d told me before: Online ordering was killing them. GrubHub and the others take 30% of every order. Profit margins were just 5%. So if that continued, they’d lose everything,” he says.
Guild knew he had to quickly pivot. By the last week of March, he committed to redesigning the website builder to optimize for online ordering. The V2 product was ready to launch by May.
It was an overhaul born out of existential threat, but it proved to be a blessing in disguise. “I wouldn't truly know what it would feel like to have ‘people lining up out the door’ until we pivoted. That's when growth became hyperbolic,” he says. “The pandemic was ultimately a forcing function that accelerated us toward the product our customers actually needed.”
Early signs of product-market fit
Guild says pivoting the product from a “nice-to-have” tool to a lifeline for restaurants to survive the pandemic is what ultimately bent Owner’s growth curve. He knew he’d struck gold when demo requests got out of control.
“We had hundreds of demo requests every week. I had to create group demos to fit in all the restaurant owners who’d requested one,” he says. “From 7 AM to 7 PM, every day, I was in demos. And they’d all been booked inbound.”
The pivot to online ordering prompted Guild to rethink the premium pricing strategy to better align Owner’s growth incentives with customers’. ”I'd long had this suspicion that it was hard to acquire customers in the beginning because we were the most expensive software for small business owners by a wide margin,” he says. “So I thought, ‘What if we just charge the restaurant guest a $1.50 fee for every order?’ That way, we’re incentivized to drive as many orders as humanly possible.”
He credits that pricing change as a key ingredient in Owner’s rapid growth during the pandemic. “That combination of the product being essentially free and extremely needed is what led to that explosive traction.”
Scaling up
With demand soaring in summer 2020, investors eventually came knocking. Guild had successfully bootstrapped the company up until that point, but he says raising a Seed Round allowed him to scale the team to start supporting Owner’s breakout growth.
With that fresh cash, he was able to add engineers, a sales team and a support team. And in early 2021, he brought on Dean Bloembergen as co-founder and CTO.
While he’s deeply grateful for venture funding to build out the Owner team, he doesn’t regret starting on the bootstrap route. “The biggest benefit of not raising money until that point was the mindset it instilled,” he says. “I spent two and a half years as a product builder, support rep, salesperson and BDR. That taught me a ton about how those functions work, and got to learn from our customers on the ground. I was the first point of contact.”
Soon after, Guild started to feel pressure to deliver even more value for Owner’s customers. “At this point, I started hearing, ‘Adam, this online ordering thing is awesome, but it's so expensive and time-consuming to use 15 other tools to power every other piece of our restaurant online. Can you do those things for us too?’ So we said, ‘Yes, we can,’” he says.
He took that direct product feedback as an affirmation of the strong relationships he’d built with customers. “With the other solutions our customers used, they had to speak to support reps or account execs who couldn’t give the same level of feedback, business owner to business owner,” he says. “And I felt like I’d earned their trust by making a promise to continue to help them drive their sales. For me, keeping that promise meant customers could be a proactive thought partner in our product roadmap.”
So one by one over the next year, Guild and the expanded team began building out different point solutions into the platform to consolidate customers’ tech stacks, including:
- Reviving the website builder to pair with online ordering
- CRM
- Email and text messaging
Guild says these additional products made the core online ordering product stronger. “The online ordering product drives more sales if it pairs with a high-converting website. And the website drives more opt-ins to email marketing and CRM, both as a function of the lead capture forms on the website and through the online ordering product. So there's this beautiful synergy to having all of these products work together,” he says.
He was firm about bundling all of these products into one standalone offering — and reintroduced the subscription pricing model. “We said, ‘You can't buy one without the other because they work so well together,’ which we still do today,” he says. “After seeing what happens when all of these different solutions work in conjunction versus independently, I explained to customers that it wouldn’t be in their best interest to use one of the products as a standalone.”
On the decision to go multi-product a bit sooner than is typical, Guild says he wrestled with it, but ultimately went with his gut. “This was before the ‘compound startup’ was coined by Parker Conrad. It was pretty contrarian to go multi-product so early. And this was at a time where our point solution had just started to work,” he says. “Going multi-product earlier ended up being one of the best decisions we ever made because it improved everything. It improved the customer's results. It improved our retention rates. It created a higher perceived value and willingness to pay.”
As Owner has grown and eaten up more of the market share, Guild has picked up these two lessons about building for SMBs:
- Learn from — don’t fear — your competitors. “I believe competitors should be viewed as resources to learn from,” he says. “You can think of them as free research and development factories that are constantly running a bunch of experiments on the same group of customers. And when some of those experiments work well, it makes a ton of sense to just shamelessly copy that approach to that specific product to bring that benefit into our platform. We’ve done that a ton over the years — we’ll distill down what worked for a competitor and build it into our own product.”
- Get the LTV to CAC ratio to work in your favor. “To make the very brutally difficult economics of serving local business owners work, make sure that the lifetime value (LTV) to customer acquisition cost (CAC) ends up being well over three to one. And the way you do that is by both dropping CAC through finding resourceful and creative ways to distribute the product, and maximizing LTV through delivering so much value in the product that you're able to charge a high price for it.”
Looking forward
With the multi-product business humming along, Owner’s revenue soared past $1M in 2021, and eventually closed Series A and B funding rounds. With its recent $120M Series C earlier this year, Owner entered the $1B valuation club.
As Guild looks ahead to Owner’s future, he’d like to widen the product's impact to serve all kinds of business owners. To do that, as CEO of a scaling company, he’s focused on being the Nick Fury for his team. That means doubling as chief recruiting officer.
“In the Avengers, there's this character, Nick Fury, who doesn't have any superpowers of his own, and he humbly acknowledges that. But his superpower is constantly scouring the world for people who do have superpowers and can be a part of this bigger team and mission. So that's how I view my role as CEO now. More than 30% of my waking hours go toward recruiting,” he says.
He’s also keeping that chip on his shoulder from his days as a teenage upstart entrepreneur. “When I dropped out of high school, I had this fear that I was going to fall behind everybody who went to fancy colleges and was on the traditional track. So I promised myself that while my traditional education was ending, my self-guided education would ramp up,” he says. “That has manifested in having the humility and self-awareness to be a life-long learner.”