Ep 37: Scaling from $5M to $38M: The Unreasonable Path to Startup Success

 Timestamps:

00:51 Why Russell Left the Corporate Giants for a Startup Rollercoaster

03:20 Scaling from $5M to $38M ARR in Five Years

06:02 Partner-Centric Models are Not for the Faint-Hearted

08:02 Building a Global Team is Harder Than You Think

10:14 The Importance of Repeating Yourself—Endlessly

12:04 Why Hiring for Attitude is the Key to Success

14:31 The Secret Sauce to Partner Success

19:12 The FOLAD Factor: Fear of Looking Like a Dick

23:56 Building a Culture of Trust and Accountability

25:25 The Unreasonable Person Drives Change

25:56 Unreasonable Expectations are Key to Growth

29:38 Managing Investor Expectations is a Delicate Balancing Act

Why I Left the Corporate Giants for a Startup Rollercoaster

I’ve been in the corporate game for decades, working with companies like Xerox, IBM, Hyperion and Wolters Kluwer. After years in senior roles, I took a leap into startup life with Dubber. It wasn't a traditional move, and I can’t count how many times people have asked, "Why would you leave the safety of a corporate behemoth for the uncertainty of a startup?" The truth is, after years of 24/7 work in large corporations, I was burned out. I needed something to test me in new ways, and nothing does that like a scale-up business. So, I made the jump, and it’s been a ride ever since.

What They Don’t Tell You About Startup Life

I went from working for a 185-year-old Dutch publishing business to a company with 35 people and three salespeople. Sounds like a nightmare to some, right? But the reality is, the fundamentals of scaling a business are the same whether you’re in a centuries-old company or a fast-paced startup. What really threw me off wasn’t the transition itself, but the intensity. The levers you pull in a startup are more sensitive. Every decision feels like life or death—because, quite literally, it can be.

Scaling from $5M to $38M ARR in Five Years

Scaling Dubber was no walk in the park. We went from $5 million to $38 million in ARR in just five years. So, how did we do it? We didn’t try to do everything ourselves. Partnering with industry giants like Cisco and Microsoft was key. Their market leadership in cloud telephony gave us the credibility we needed to scale quickly. It’s like grabbing onto a rocket when it’s just about to take off. But here’s the catch: these partnerships weren’t just handed to us; they were carefully cultivated.

 Partner-Centric Models are Not for the Faint-Hearted

Dubber’s strategy was to be a partner-centric business. I’ll be honest—this wasn’t always easy. There were countless times when I wanted to just go after deals myself. When AT&T dangles a Bank of America opportunity in front of you, it’s hard not to bite. But we had to stay true to our core: we weren’t an enterprise sales organization; we were partner-centric. That discipline paid off in the long run, but trust me, it came with a lot of heated “debates” (let’s call them that) internally.

 Building a Global Team is Harder Than You Think

One of the toughest challenges in scaling Dubber was building a cohesive, global team. You’ve got time zones, cultural differences, and communication issues to deal with. I learned the hard way that you can’t just throw people into roles and expect them to swim. Jeff Weiner’s words, “just as you’re sick of telling the message, your team is just starting to listen,” hit home for me. I had to slow down the hiring process and really focus on over-communicating our mission, our values, and what we stood for.

 The Importance of Repeating Yourself—Endlessly

One of the mistakes I made early on was assuming that everyone on the team just "got it." I can’t count the number of times I’ve had to repeat our vision and goals. But here’s the thing: when your company is scaling, you need to keep hammering the message home until everyone, from your top salesperson to your newest hire, understands it. And guess what? Just when you’re tired of saying it, that’s when they’re actually starting to listen.

Why Hiring for Attitude is the Key to Success

One of the most painful lessons I learned was the importance of hiring for attitude, not just skill. We were too quick to hire people who looked great on paper but didn’t have the resilience to survive in a startup. People from big telcos like Cisco or Verizon often struggled in our fast-paced environment because they weren’t used to doing things on their own. They expected everything to be handed to them. What we needed were people who had a hunger to win—people who were scrappy and resourceful. And when we found them, it made all the difference.

The Secret Sauce to Partner Success

We learned pretty quickly that not all partners are created equal. We spread ourselves too thin initially, trying to work with every Cisco and Microsoft partner we could find. Enter Sarah Appleby and her “Secret Sauce Calculator.” This tool helped us assess whether a partner was really worth our time and effort. And let me tell you, one of the best feelings is when a partner admits upfront, “We’re just not that into you.” It’s like dating—better to know early and save yourself the heartbreak (and wasted resources).

The FOLAD Factor: Fear of Looking Like a Dick

We ran into a funny (and frustrating) phenomenon with some of our partners’ sales reps. We called it the FOLAD factor—Fear of Looking Like a Dick. No one wants to get in front of a customer and not know what they’re talking about, especially with a complex product like ours. To overcome this, we focused on building confidence and competence in our partners. The more they knew, the more they sold. It was a virtuous cycle, but getting there took time and patience.

 Building a Culture of Trust and Accountability

You can’t just inject culture into a company—it’s something that grows organically, especially in a startup. At Dubber, we were intent on being a high-energy, low-pretense organization. We wanted people who were hungry to win but also willing to share knowledge. Balancing that was tough, especially when high-performing salespeople tend to be lone wolves. But we managed to build a team that was driven, data-rich, and, most importantly, transparent. Trust was the foundation of everything we did.

Unreasonable Expectations are Key to Growth

Here’s a controversial take: sometimes you need to be unreasonable to succeed. I learned that from reading about Don Valentine and Sequoia Capital. The world doesn’t change because of reasonable people—it changes because of those who push the boundaries. I had to find a balance between building trust with my team and pushing them to achieve more than they thought possible. Sometimes they thought I wasn’t listening, but the truth is, I believed we could always do better, and I wasn’t going to settle.

Managing Investor Expectations is a Delicate Balancing Act

As Dubber scaled, managing the expectations of investors became one of the toughest challenges. At one point, we were growing ARR by 60-70% year-on-year. But then, shareholders started asking, “Where’s the path to profitability?” It’s a classic startup dilemma: grow fast or grow profitably. We were stubborn about continuing our rapid growth, but eventually, we had to shift focus and start showing a path to profitability. It wasn’t easy, but simplifying the message for our shareholders and reiterating it constantly helped.

 Why Authenticity is the Best Leadership Style

Over the years, I’ve learned that being authentic is the best way to lead a team. You can’t fake it in a startup environment—people will see right through you. I’ve always been an open, transparent leader, and that’s helped me build trust with my team. But being authentic doesn’t mean you have to be soft. In fact, I believe that you can be both trustworthy and have unreasonable expectations. It’s a fine line, but when you get it right, the results speak for themselves.

Data-Driven Culture is a Must in a Scale-Up

At Dubber, we were laser-focused on being data-driven. You can’t scale a global company without having a clear understanding of where you are and where you need to go. We used data to align our team, set accountability, and drive performance. The best part? Data doesn’t lie. It gave our high-performing salespeople the direction they needed to succeed, and it kept us all on the same page, whether we were in Melbourne, Sydney, or halfway across the world.

 The Unreasonable Person Drives Change

I’ll end with this: unreasonable expectations are the key to change. The world doesn’t grow because of people who accept things as they are. It grows because of people who push for more. At Dubber, we pushed ourselves every day to be bigger, better, and bolder. And while it wasn’t always easy, it’s the reason we scaled as fast as we did.

Summary

Reflecting on my journey from corporate giants to scaling a startup, I’ve learned that success in a startup requires resilience, focus, and a willingness to be unreasonable. Whether it’s building a global team, cultivating the right partners, or managing investor expectations, every challenge is an opportunity for growth. And through it all, being authentic, data-driven, and relentless in your pursuit of success will make all the difference.

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