Alex Turnbull exited his first company, then bootstrapped Groove to $5M ARR.
Now, he's taking an add-on product for Groove and turning it into a standalone, platform-agnostic product — a product that he audaciously plans to grow to double what Groove is making.
I caught up with him to understand how he did it with Groove, and how he plans to hit that goal with Helply. Here's what he had to say. 👇
I was working on another startup — a social, industry-agnostic CRM — as a cofounder when I thought of Groove.
This was back in 2009 and I was wearing multiple hats, including product management and customer service. We had just started using Zendesk instead of managing support via email, and I thought there was a better way to do it.
On the agent side, I wanted a more user-friendly application. On the customer side, I didn't think they should have to see "reply above the line" or even know there's an actual ticket.
So, right around the time that we sold that startup for $15M, I put on my PM hat, spinning up wireframes and mapping user journeys. I had no technical skills. To this day, I still don't. So, I used $350k from my exit to fund the alpha and beta versions of Groove.
It wasn't even validated, but I knew from my experience in customer service that it was needed. It was a bit of a risky play.
Groove is a SaaS customer support helpdesk. It has been around for 12 years and has $5M ARR.
And now, I'm bootstrapping Helply, a platform-agnostic AI customer service agent. It hasn't launched yet, as we're in the process of validating it. I'm 150 customer demo calls in, with a goal of 500.
Helply started with Groove, so there's a big question mark around whether the agnostic chatbot can gain steam and traction outside of the Groove customer base. But we know it's a very needed process because the idea was born from the needs and requests of both Groove and non-Groove customers.
As you might imagine, I don't have a ton of spare time to build Helply while scaling a $5M ARR company. There are three reasons I'm doing it.
First, the AI revolution is here and it’s shaking up customer support for better or worse. We have AI functionality at Groove. But, having a product with AI at its core in Helply will help us meet the AI evolution head on, and hedge our bets (while staying agile) as AI continues to impact the support role.
Second, it's what the market needs. We’re not building Helply on a whim. Helply originally started as an AI chatbot just for Groove. But as we conducted hundreds of interviews with existing Groove customers and potential customers, something became apparent. — the customers who used our competitors' solutions also needed our solution.
This gave us the evidence that this is needed in the market. We are building the solution they need.
And third, I miss early stage startups. Somewhat selfishly, I miss the buzz. Groove is still at an early stage in terms of revenue, but I love getting in at the ground level, and building brand new products.
This is what I’m most passionate about doing.
I don’t raise outside funding. I'm completely bootstrapped.
Being bootstrapped allows me to do the following without the pressure of VC funding:
Be profit-driven, focusing on EBITDA instead of just growth.
Challenge the company and myself to be EBITDA-focused, with a sustainable, profitable business model.
Be customer-driven and customer-led in our growth and profit strategies.
Even now that Groove is making seven figures per year, we're staying scrappy. Being lean and capital efficient needs to be in your blood if you are a bootstrapper or indie hacker. It is a core requirement.
Never transition away from being scrappy.
With that said, the problem with being bootstrapped is that we aren't able to move as fast as the competition in engineering and product. This has always been a challenge for us.
In Groove's market, you have companies like Zendesk and others that are institutionally backed with hundreds of millions in capital. Some are even publicly traded. That's hard to compete with on an engineering and product level.
The solution is to stay nimble, but have processes in place that allow you to execute your quarterly goals in a very aligned and efficient way.
Don't just have the entire company or team go off into a corner and come back after a quarter. Consistently follow the Entrepreneurial Operating System (EOS) of rocks, pitches, and weekly L10 meetings. This automatically puts checks and balances in place so you don't make any irrational decisions.
The pitches, which are designed to help you achieve buy-in from stakeholders around that quarter's goals, are themselves one of the biggest pieces to making rational decisions. You put so much time up front into the hypotheses, research, and planning for what will contribute to that rock (our name for goals) that by the end, you have crystal clear clarity and alignment.
Whether or not you use EOS, processes are the answer to funded competition. When you stick to some level of process, you can work pretty damn efficiently and do a lot with less.
Groove grew almost entirely through founder-led marketing via my "Journey to $100K" blog and SEO-driven customer service content.
We were featured in over 100 publications, all from organic founder-led marketing efforts, and that fueled word-of-mouth and powered our growth.
All we had to do was publish and document everything with full transparency. The community grew organically and, therefore, so did the outside press. The only strategic move we made was using the blog and the posts as an opportunity to layer in SEO.
After seeing its success with Groove, I'm using founder-led marketing for Helply as well, albeit on LinkedIn instead of via blog. Blogging has become an “old school” and less effective medium. Plus, LinkedIn is where our ICP — CEOs and operational leaders — are active. So I'm posting 365 days a year on LinkedIn and building in public with full transparency.
My advice: If you're a founder, forget about the vanity metrics. Focus on the unquantifiable power of building in public, which has this insane power that opens doors you never knew existed.
It all comes down to the community, the energy, and the growth that comes from being open and transparent. It's all about creating a continuous stream of engaging, authentic narratives.
We want to grow Helply in a way that's led by education and community while leveraging affiliates, partnerships, modern inbound/outbound, and founder-led marketing playbooks.
When I was blogging about Groove's Journey to $100k MRR, I NEVER looked at a metric for 3 years. I just knew that as I shared more, trials started to come in, and the community FELT like it was starting to buzz.
Here’s the thing about building in public: Every new startup is constantly fighting for its life. This inherent conflict is captivating. The drama is high.
Every meeting, every hire, every experiment, and every mistake is an event in the story arc.
Your job with founder-led, B2B marketing is to take this continuous stream of engaging, authentic narratives, and report on it. Just tell your story every day from the frontlines. That’s it:
Share your journey and insights: Attract followers and generate interest.
Engage actively: Connect and comment on others' posts to build a community and leverage their audiences.
Ask for feedback: Proactively seek input on your product to generate connections and open opportunities for demos.
There is no risk other than the discomfort that arises from being vulnerable.
There's a fascinating playbook with inbound and outbound paired with founder-led marketing.
With tools available today, like Clay and Instantly, you can do a lot of outbound alongside inbound. The goal is to have it be additive with your personal brand so you can consistently create content that you can repurpose and leverage in newsletters, courses, and other opt-ins that lead to your email list.
This is where you'll develop your lead and pipeline generation.
It doesn't happen overnight; you need to do it for a solid year to test and systematically leverage the playbooks that allow you to automate outbound while using founder-led marketing to generate conversations with intent-based signals.
On a basic level, what you're trying to do is get people to your site (inbound) — the homepage, newsletter, or wherever. From there, you're doing the traditional approach: Capturing their email through opt-ins.
The non-traditional way involves the new RevOps stack with companies like RB2B, which anonymizes visitors.
So when people come to Helply, it identifies who they are on LinkedIn. You then use a program like Clay to automatically route that contact and potential lead into Clay, which enriches the contact with their info and other details needed to effectively reach out. Next, you use Smartlead or Instantly to do the outreach, and a traditional CRM to manage the actual deals that are flowing in.
The RevOps stack is a way to streamline this entire process because it can be largely automated and run on autopilot, which is fascinating. So now, you're combining the two approaches — traditional and non-traditional — in a systematic way to really drive demos and leads. This is the stack of tools that all lead engines are using.
And here's a cautionary tale. My "$100K journey" blog was my unfair advantage, but I stopped doing it four years in when a rebuild went south. In short, I let imposter syndrome pull me out of the public eye as I was questioning my worth and decisions.
Don’t give in to imposter syndrome. It's debilitating. And it can hinder your progress even if your decisions are based on rational thinking. I had to learn to push through those toxic thoughts and keep going.
The cure to imposter syndrome is what I call "proof of work":
Take the time to research your position, comb through the data, talk to customers ad nauseam, steel man counter arguments, pitch your shareholders to achieve their buy in. If you take time to do proof of work, it makes it harder and harder for imposter syndrome to creep in. And if it doesn't "prove" itself, then that's where you learn the most.
And beyond that:
Remind yourself of past successes and the rational basis for your actions.
Focus on a mindset of iteration and incremental improvement.
When doubt creeps in, focus on evidence and data to validate your decisions.
Seek support from mentors or peers and practice self-compassion to combat negative thoughts. Keep pushing forward despite doubts.
At the end of the day, you just have to do it. Stop talking. Get your hands dirty.
Even if you don't have a product, go out and find 100 people in your ICP, talk to them, do research, and validate the product. Share your ideas.
Then, once you have that validation and data move to the next stage. Make your prototype. Then do your beta. And just keep on doing shit.
In the early days of my entrepreneurial career, I was a bit naive, thinking about being rich and famous versus being very happy and living a great life. Now, my goal in entrepreneurship is to crack the code on feeling peaceful while still building something sustainable. Less stress, but just as much hustle.
The truth is that I’m hustling now harder than ever, but I stop Friday afternoon. I'm hustling 4.5 days a week. I don't bring it into the weekend.
So, with that in mind, I plan to maintain a highly profitable, sustainable company. It doesn't need to be a unicorn. If Groove grows 12% year-over-year, I'm very happy.
Helply, however, has an audacious goal to go from $0 to $10M ARR, with a higher TAM and lower barrier to entry. Follow along on the journey; we’re going to be sharing it all — the founder-led playbook, the affiliate playbook, the RevOps GTM playbook, and the content SEO playbook.
You can find me on LinkedIn. And check out Helply.com and Groovehq.com.
Leave a Comment
Love your thoughts. Great and well researched article as well.
Keep up the good work man! :)
Very insightful post, especially the bit about doing founder-led marketing. I typically tend to lean on social media for my strategy.
A great read. It's refreshing to see examples of bootstrapped companies thriving in markets typically dominated by venture capital-backed enterprises.
BTW, the LinkedIn link at the end of the article is broken.
thats amazig
Spending $350k on an MVP without technical skills shows boldness and deep industry insight. Your transition to Helply and commitment to bootstrapping against giants like Zendesk is truly impressive—kudos for staying agile and focused on sustainable growth!
One thing true is combing inbound and outbound becomes a monster combo
This is a good interview format.