How Alex Exited his First Company, then Bootstrapped Groove to $5M ARR.

Table of Contents

• 🚀 Founder Journey: Alex Turnbull on Building Groo …

  • 💸 Investing $350K in an MVP

  • ✅ How Alex Is Validating Helply

  • 🎯 Three Reasons Alex Is Building Helply

  • 💡 Why Bootstrapping Helply Is the Right Move

  • 🔧 Solving the Challenges of Bootstrapping

  • 🚀 Founder-Led Growth: The Groove Playbook

  • 📈 How to Nail Founder-Led Marketing

  • 🔄 Blending Inbound/Outbound with Founder-Led Grow …

  • 🧠 Overcoming Imposter Syndrome with Data

  • 🛠 "Just Start" — The Most Important Step

  • 🌱 Less Stress, Bigger Goals

  • 📝 Editor's Commentary

🚀 Founder Journey: Alex Turnbull on Building Groove and Helply

Alex Turnbull exited his first company and bootstrapped Groove to $5M ARR. Now, he's turning an add-on product for Groove into a standalone, platform-agnostic solution — Helply. Audaciously, Alex aims to grow Helply to double Groove's revenue!

We caught up with him to learn how he grew Groove and how he plans to scale Helply. Here's what Alex had to say about his entrepreneurial journey and future goals.👇

💸 Investing $350K in an MVP

Back in 2009, while managing customer service for a previous startup, Alex spotted a gap in the market: the need for a user-friendly, seamless customer support tool. With $350K from his exit, he funded the alpha and beta versions of Groove, even without technical skills or validation.

It was a risky bet, but Alex trusted his experience in customer service to guide the way. If you're building an MVP today, this underscores the importance of investing in your vision, even without a perfect prototype.

✅ How Alex Is Validating Helply

Helply started as a chatbot add-on for Groove. But as Alex conducted over 150 demo calls with a goal of 500, he discovered that many non-Groove users also needed an agnostic AI customer service agent. Now, the team is validating Helply for broader markets beyond Groove’s customer base.

Helply could be an even bigger hit because it's born out of real customer feedback and market needs. That’s a key takeaway for any startup founder: validation is crucial, and understanding customer pain points can guide product decisions.

🎯 Three Reasons Alex Is Building Helply

Why build Helply while running a $5M ARR business like Groove? Alex gives three reasons:

1. AI Evolution: The AI revolution is here, and Helply’s AI-first approach ensures they stay agile as customer support evolves.

2. Market Need: Extensive customer interviews show Helply can serve a much broader audience than Groove.

3. Startup Buzz: Alex admits he misses the excitement of building something from the ground up.

If you're eyeing new ventures, passion and market demand are key motivators to pursue new challenges, even with an existing successful business.

💡 Why Bootstrapping Helply Is the Right Move

Alex remains committed to bootstrapping. By staying independent, he's able to keep Groove and Helply customer-driven and profitable, without the pressures of venture capitalists.

He emphasizes the value of focusing on EBITDA, not just growth, and maintaining a scrappy, lean operation. According to Alex, being scrappy is essential for long-term sustainability and success, and he plans to apply the same bootstrapping principles to Helply.

Want to learn more about bootstrapping strategies? Check out this guide.

🔧 Solving the Challenges of Bootstrapping

Of course, bootstrapping comes with challenges. Competing against well-funded companies like Zendesk can be tough, but Alex uses systems like the Entrepreneurial Operating System (EOS) to stay aligned and efficient. This allows Groove to work smarter, not harder, and focus on executing quarterly goals.

If you're a bootstrapper, having a solid process in place is critical for competing against larger, funded competitors.

🚀 Founder-Led Growth: The Groove Playbook

Groove’s growth came from Alex’s founder-led marketing efforts, including his popular Journey to $100K MRR blog series, which was featured in over 100 publications. His advice for founders: be transparent, build in public, and leverage your community.

Now, Alex is applying this playbook to Helply via LinkedIn instead of blogging. He posts daily, focusing on transparency, community, and education.

Looking to build in public? Start by consistently sharing your journey and insights, just like Alex is doing on LinkedIn.

📈 How to Nail Founder-Led Marketing

Founder-led marketing is all about storytelling. For Groove, Alex never tracked metrics for three years — he just shared openly, and trials began rolling in. Authenticity is key, and each moment of a startup’s journey is a narrative that attracts an audience.

To do it right:

1. Share Your Journey: Be transparent about your wins and failures.

2. Engage with Others: Comment, share, and connect with your community.

3. Ask for Feedback: Validate your ideas and iterate.

Founder-led marketing is powerful, but it takes time to build momentum.

🔄 Blending Inbound/Outbound with Founder-Led Growth

Alex is leveraging tools like Clay and Smartlead to combine outbound strategies with founder-led inbound marketing. He’s automating the process of reaching out to potential customers while nurturing leads through personal branding and content creation.

By pairing inbound and outbound efforts, you can scale marketing and sales in parallel — a tactic Alex plans to use to fuel Helply’s growth.

🧠 Overcoming Imposter Syndrome with Data

When the Journey to $100K blog hit a bump, Alex let imposter syndrome pull him away from the public eye. But now, he’s learned that the key to overcoming self-doubt is focusing on proof of work — data-driven validation of your decisions.

Alex advises entrepreneurs to:

• Validate with Data: Research, customer feedback, and solid metrics help quiet doubts.

• Lean on Past Successes: Remember what you’ve achieved.

• Push Forward: Don’t let negativity hold you back.

🛠 "Just Start" — The Most Important Step

Whether it's launching a new product or starting your entrepreneurial journey, Alex’s advice is simple: just start. Don’t wait for perfection — gather data, talk to your audience, and keep iterating.

🌱 Less Stress, Bigger Goals

These days, Alex focuses on maintaining balance. Despite working harder than ever, he’s clear about boundaries — no work on weekends and a sharp focus on a sustainable, profitable future.

Helply’s goal? A bold one: $10M ARR. But with Alex’s disciplined approach, it seems well within reach.

📝 Editor's Commentary

It’s inspiring to see how Alex is applying the lessons learned from Groove to Helply. By embracing both the excitement of building something new and the scrappiness of bootstrapping, he's setting a course for long-term success. His story reinforces the importance of balancing audacious goals with a grounded, data-driven approach. Founders can learn a lot from Alex's transparency, his relentless focus on customers, and his ability to stay lean while scaling.

Are you a B2B founder or seller looking to generate more leads through LinkedIn? See how friendli can help automate lead generation using your LinkedIn network!

Cheers,

Matt