Alex Turnbull once hired his sister to help him run his company, and she gave him an instruction that was surprisingly difficult to obey. “Go ahead. Just have fun.” She stared at him. “Having fun yet?” It was a small domestic intervention with a corporate target. Groove had made fun one of its core values. Elizabeth, an experienced business coach, wanted her brother to consider whether a command to enjoy yourself was a useful way to manage a software business.
He had already advertised those values to the world. There had been a process, a published explanation and even a Slack bot to help colleagues recognize one another for living them. Now he was publishing the correction. The company had let enjoyable projects displace tedious, necessary work. Clear specifications, difficult conversations and proper accountability had suffered. A cheerful word had become an expensive permission slip.
Turnbull’s career contains plenty of numbers. One earlier business sold for $15 million. Groove eventually reached roughly $5 million in annual recurring revenue, he says. But this encounter with his sister offers a more revealing introduction. He is a founder who will put his working assumptions on display, then return to explain why some of them were wrong. The homework is public. So are the red marks.
Before there was an audience, there was a customer
In 2006, Turnbull was doing freelance work for financial advisers. Their information was scattered across spreadsheets and notes; following up with clients was harder than it needed to be. He built Upswing CRM to address the mess. His account of those beginnings contains little ceremony. There was a recurring problem, someone willing to pay to solve it, and software that needed improving.
Upswing later became part of Bantam Live, where Turnbull was a co-founder and product manager. The proposition combined customer relationship management with the social web. Before building, he says, he cold-called and interviewed more than 100 prospective customers. Listening was becoming a repeatable part of his work, well before he had a readership to tell about it.
Constant Contact bought Bantam Live’s assets in February 2011 for $15 million in cash, subject to adjustments. The transaction gave Turnbull an exit and another irritation to investigate. At Bantam, customer support software had felt cumbersome. Small teams needed to answer people quickly; the available tools asked them to navigate more machinery than they wanted. Groove began with that very particular complaint.
A small company, with its sums showing
Groove’s beta arrived in July 2011. The public launch followed in November 2012. In his early account of the business, Turnbull also described raising a $1 million convertible note from angels after exploring venture capital. That detail matters when reading the later shorthand about bootstrapping. His preference for independence developed through actual financing choices, rather than appearing fully formed on a motivational poster.
He also discovered how easily a product sold on simplicity could become complicated. Looking at larger competitors’ websites made Groove’s own presentation seem inadequate. Inside the product, additional features created their own confusion. The team eventually stripped back the experience and moved secondary functionality into an app store. Turnbull made these misjudgments part of the company’s published history. Customers could read the explanation as well as use the result.
In 2013, he began documenting the journey toward $100,000 a month in recurring revenue. A revenue target supplied the plot. Product decisions, disappointing experiments and small improvements supplied the episodes. Readers had a reason to return that extended beyond a new feature announcement. They could follow a business while it was still trying to work things out.
Ten weeks into the experiment, Turnbull reported more than 100,000 unique blog visitors and a monthly revenue increase of more than 10 percent since the blog began. He thanked people for commenting as well as reading. The discussion, he wrote, could teach him as much as producing the post. A company trying to find customers had also assembled people willing to argue with its homework.
- 2011Groove beta opens
- 2012Public product launch
- 2013The $100K/month diary begins
Transparency still needs a distribution plan
A candid post does not circulate through moral force alone. Turnbull’s account of a 2013 conversion survey is pleasingly short on retrospective grandeur. Three days before launch, he realized the team was asking readers to spend several minutes finding and sharing business data, without having thought seriously enough about why they would bother. The survey needed promotion, incentives and partners. It needed rather more than a publish button.
The team assembled prizes, involved other companies and changed its editorial calendar. Instead of repeating the same request, it published useful material connected to the survey and placed a relevant guest article with KISSmetrics. More than 1,500 responses eventually came in. Here was the less photogenic half of building an audience: arranging reasons to participate, finding people who could help, and doing the follow-up.
His advice about mentors has the same practical character. Turnbull has described starting without a powerful network and building relationships with people who knew more than he did. The entrepreneur whose writing others consult was doing plenty of consulting himself. There is something reassuring about that arrangement. Expertise can accumulate through specific questions; it need not arrive as a complete personality.
By the time he sat down with Mixergy’s Andrew Warner, the blog had already created a long-running conversation between them. Warner recalled an email from September 2013 and repeated attempts to arrange an interview as Groove passed revenue milestones. The eventual conversation had a backstory because the company’s progress had been visible. Turnbull had given a stranger enough detail to become a persistent, interested reader.
“I’m not even remotely the only one responsible for Groove’s success.”Alex Turnbull, thanking the blog’s readers
The founder is also on ticket duty
Turnbull’s later account of reaching $5 million in annual recurring revenue with five people emphasizes the unglamorous details of running small. Everyone answered support tickets, including him. A bug went to someone who could fix it. A recurring question could become documentation. An awkward interaction could point toward a change in the product. Customer service supplied work and information at the same time.
The arithmetic is striking, but it is a reported snapshot, rather than a claim that Groove always had five employees. In that account, the business operated without a dedicated sales team, allowed customers to try the product themselves, and kept a close eye on recurring expenses. He reported profit margins around 50 percent. The ambition was to make a small organization productive enough to remain small.
He has also been willing to defend a plateau. In a later LinkedIn post, he compared a profitable $5 million software company with a pizza shop doing the same revenue. The pizza owner would have reason to celebrate; technology circles might ask why there were not already 100 locations. It is an effective comparison because the absurdity fits comfortably into a takeaway box. The owner still gets to decide how many ovens to buy.
There are limits to a celebratory reading, and Turnbull supplies them himself. Recent writing has described years of flat growth and renewed customer research. A profitable company can still need a different product. His interest in independence does not eliminate commercial pressure. It changes who gets to decide what to do about it, and how long they can spend finding out.
The surfer and the revised rulebook
Away from the revenue reports, Turnbull is based in Newport, Rhode Island, and likes surfing. His short personal bio pairs an affection for simple software with an affection for big waves. When Groove first developed its values, the team ended up with the acronym SURFS. He acknowledged that the surfing connection made the result especially appealing to him. A founder’s enthusiasms have a way of finding the stationery.
The later revision is therefore more interesting than a routine culture exercise. His sister Elizabeth helped him question a system he had personally liked and publicly endorsed. Replacing vague enjoyment with execution meant clearer processes and responsibilities. Even a social ritual changed: Fun Fridays became Friday Wins, with people discussing what they had achieved. Pleasure could follow completed work instead of serving as the selection criterion.
His description of his own morning routine was similarly free of executive theatre. Working from home, he put his commute at about 20 feet. Cereal, coffee and the desk figured in the account. Consistency mattered to him more than novelty. For someone whose professional life involves publishing lessons, it is a useful detail: breakfast did not have to become another lesson in exceptionalism.
These small admissions give the public business diary its texture. A surfer likes a surfing acronym. A brother needs his sister to challenge him. A remote chief executive walks a few feet to work. None requires an origin myth. They help explain why the writing has room for mistakes: the person making the decisions remains visible inside the business.
Another name on the door
The latest chapter returns to customer support with Helply. The company’s current announcement says Groove is now Helply, alongside a new helpdesk rebuilt around AI. Existing Groove accounts and workflows are to continue, with customers able to explore the new product separately. Turnbull is asking people who chose his software once to consider a second choice, without imposing a migration deadline.
“I would rather earn the move than schedule it,” he writes. That sentence carries more weight than a launch adjective. Software companies can change names instantly; customers have working days organized around the old product. The promise gives those customers a measure of control over a decision that could otherwise be made for them.
Turnbull is also extending the public diary. Zero to $10M packages his ongoing work and lessons for other founders, and his newsletter sets out an ambition to build another business toward $10 million in annual recurring revenue with substantial profit margins. He has recently announced a push into YouTube, using a production team so he can record while others handle editing and publication. The medium is changing; the willingness to narrate the attempt remains.
His story is still open. A sale did not end the urge to build. A successful blog did not settle the operating questions. Profits did not remove the need to reconsider a product, and a printed set of values did not survive contact with every stage of the company. Turnbull keeps returning with another draft. For the reader, the attraction is the chance to see the crossings-out before somebody tidies the page.