From “Wolf of the Wall Street” to “The Social Network” with Adam Robinson

In the latest episode of Smooth Operators Guide by LiveDocs, Ani sits down with Adam Robinson, CEO of Retention.com and RB2B. Adam's career trajectory from the finance world to the tech industry is both fascinating and inspirational.

He is the mastermind behind RB2B and Retention.com, who uncovered some major strategies that propelled his business to extraordinary heights. Adam has previously held roles at companies such as Pavilion and Nostra AI.

He shares how he’s helping eCommerce brands unlock new revenue streams by tackling cart abandonment, boosting ad efficiency, and building first-party audiences, all in a world where third-party cookies are fading fast. He builds capital-efficient, lean, high-growth, highly profitable, bootstrapped SaaS businesses. 

Let's get into it:

Ani: Welcome to the show, Adam! Could you start by introducing yourself?

Adam: Thanks for having me. I’m the CEO of Retention.com and RB2B, and I’m excited to get into today’s discussion.

Ani: Your career shift from finance to tech is quite intriguing. You began at Lehman Brothers and Barclays before transitioning into tech and marketing. What motivated this change, and what have you learned from it?

Adam: I’ve always had a passion for entrepreneurship. Back in 2003, when I graduated, the startup scene was very different. It wasn’t common for young entrepreneurs to raise funds like it is today. Most ambitious students would aim for high-paying roles at top investment banks, which were seen as lucrative and a solid foundation for future opportunities.

I ended up in Lehman Brothers' credit default swap trading department. During the financial crash of 2008, this sector was heavily impacted, but I managed to make a significant amount of money. This financial cushion allowed me to take a riskier path and pursue my dream of becoming a tech entrepreneur. 

The transition wasn’t easy, startup life is tough, and I didn’t pay myself for five years. It’s a challenging journey, especially for first-time founders, as startups often consume all available cash.

Scaling Retention.com and Lessons from a Serial Entrepreneur

Ani: So, Adam, you've managed to scale Retention.com to $22 million in ARR in just four years. That's quite impressive! How did that journey unfold?

Adam: Thanks! Actually, Retention.com is my second startup. My first one reached $3 million ARR but got stuck there for four years. Retention.com started as a feature within that first business. People loved the feature but didn’t care for the rest, so we spun it out, sold the original product, and Retention.com took off.

Now, we're seeing something similar with RB2B. It’s an extension of Retention.com but targets B2B instead of e-commerce, and it’s growing even faster. I wouldn't be surprised if, in a couple of years, RB2B becomes our main focus.

Ani: It's amazing how you've evolved. With over a decade of experience, what are some key lessons you'd share with new entrepreneurs, especially those bootstrapping their startups?

Adam: Bootstrapping is tough. In the early stages, everything works against you, and the grind doesn’t ease up until you hit around $10 million ARR. But once you reach that point, you have options, whether it's hiring a CEO, selling your business, or continuing to grow without outside investment.

“A big mistake I made early on was spending money on things I didn’t need, like renting an office for the sake of ego.”

In the early days, every dollar counts, so it's critical to focus on what truly drives growth rather than vanity expenses.

The Discipline of Bootstrapping

Adam: When I first started, I made classic mistakes, buying a phone system, expensive cameras, even renting an office, without having achieved product-market fit. These were ego-driven decisions that turned out to be pointless.

If you're bootstrapping a business, remember this: reaching product-market fit will take longer than you expect. Cash flow will tighten, so avoid unnecessary spending.

One key lesson is to maintain incredibly high standards. 

“Cracking product-market fit is crucial; without it, everything becomes a grind. Strong word of mouth is vital, it's a sign that you're delivering a great product to a targeted audience who love it enough to spread the word.” 

Initially, focus on doing things that don’t scale: talk to customers, understand what they love and hate about your product, and make adjustments based on their feedback.

Ani: Everything else seems shiny and attractive, like being featured on Product Hunt or TechCrunch.

Adam: Exactly. PR and media hits might feel good momentarily, but they don’t contribute to long-term success. Product-market fit is the only thing that truly matters. Spend as little as possible until you achieve it, and then grow efficiently. Once you hit $10 million ARR, you can decide whether to raise capital and scale massively. By then, you'll have invaluable lessons about capital efficiency and resourcefulness.

Ani: Right, it sounds like bootstrapping really forces you to grow as a business leader and as a person.

Adam: Absolutely. Bootstrapping teaches you to be highly resourceful, and that discipline carries over into all aspects of life. Raising capital too early can lead to wasting money and focusing on the wrong things.

Future of Retention.com and RB2B

Ani: What are your thoughts on the future of Retention.com and RB2B? How do you see them evolving, and what key strategies are you focusing on?

Adam: Retention.com and RB2B are distinct ventures, each with its own trajectory:

1. Retention.com: Originally a feature in my email marketing app Robly, it’s now focused on eCommerce stores. We rely on high-impact methods like owned events and trade show activations due to the smaller, more specific market. Our goal is to continue leveraging these high-touch strategies as they yield better results than digital channels for our niche.
2. RB2B: This is separate from Retention.com, targeting B2B clients with a focus on LinkedIn URLs and business emails. Our approach here is heavily reliant on founder-led brand building through LinkedIn, podcasts, and storytelling. The shift from traditional sales methods to high-quality organic content is central to our strategy. For RB2B, we’re aiming to build a freemium, influencer-led model that aligns with current trends in software purchasing.

A notable example of leveraging organic social content is Ryan Babenzian’s company, Jolie, which grew rapidly through TikTok influencers and UGC. This model of combining organic reach with influencer partnerships is something we're adopting to future-proof RB2B and align with evolving sales dynamics.

‍The Journey of Founder-Led Growth and Content Creation

Ani: Founder-led growth is clearly here to stay, especially on platforms like LinkedIn, TikTok, and Instagram. You’ve been a huge inspiration for us, and we’re curious, how do you consistently produce high-quality content while growing so fast?

‍Adam: Great question! There’s a big difference between how I grew and how I manage things now. Today, I’m almost a full-time content creator. Mondays are for internal meetings with Retention.com and RB2B, but the rest of the week is spent on podcasts, creating content, and live shows. We’re even considering one-to-many coaching for startups as part of RB2B’s premium package.

Three months ago, it was different. I was still acting as CEO of Retention.com, managing 55 employees and balancing Zoom calls while figuring out the go-to-market strategy for RB2B. Juggling content creation and CEO duties was tough.

What really helped was working with Alec Paul, a consultant who’s been a game-changer. He’s not a writer but more of a creative director. We do weekly idea sessions and plan content aimed at our key audiences, founders, salespeople, and marketers. Alec manages the content calendar and strategy, while I used to write about three posts per week, batching them in 1-2 hours each.

So while I’m now focused more on content creation, the growth came from balancing multiple roles and responsibilities early on.

Building Growth Through Content Creation

Ani: So, do you knock out all three posts in one sitting?

Adam: Yeah, I try to batch it, but back then, I was doing two jobs. I was still CEO of Retention.com, managing 55 employees, completely different from content creation. I was on Zoom all day, doing internal calls and external discovery for RB2B’s product and go-to-market strategy. Now, things are more dialed in.

On the content side, growth really started this year. To stand out on social media, you’ve got to be different. Say things others won’t and offer a perspective people trust. That mix? It’s deadly.

Ani: That makes sense. So, how did you experience the growth?

Adam: It clicked when I figured out why I was writing what I was writing. For a year, I was throwing darts with my eyes closed, nothing stuck. Then, 12 months in, boom! One post hit. I wrote three more and thought, 

“If these work, I’ve cracked LinkedIn. If not, I’m still lost.” 

Bam, bam, bam, 2 million impressions across three posts. I doubled my followers from 20,000 to 40,000 in a week after struggling for a year to reach 20,000.

Now, I know the purpose behind every word. It’s about finding your voice. Once you do, you unlock content-market fit, and the magic inbound machine starts. Before that, it’s not about engagement or business, it’s about discovering your voice.

Ani: I love that, finding your voice first.

Adam: Exactly. Once you find it, you create real awareness. Look at Notion or the Clay guys, they’ve built communities around user-generated content. But the founder-led approach is more straightforward. You put in consistent, small efforts over time, and they compound. If you don’t start, you’ll never unlock that ability, and I believe it will become the only way to grow.

In B2B, it’s still behind, but in DTC, influencer-led growth is already huge. RB2B wouldn’t be growing like it is without my LinkedIn presence. Both my personal brand and the product fuel each other’s growth.

Lessons from Robly's Eight-Figure Exit

Ani: You got an eight-figure exit with Robly, an email marketing platform. What were the challenges and key learnings from selling a startup? Many of us aim for an exit or IPO, but most startups don’t get there.

Adam: For first-time entrepreneurs, aim for a smaller outcome like 3-4M ARR. It allows you to run the company with less risk, creating a cashflow vehicle for future experiments. With Robly, we were lucky. We sold to one of our customers during a hot time for acquisitions in 2021, and they were a private equity firm looking to do a roll-up. Timing and connections made all the difference.

Customer Success in SaaS

Ani: Customer success seems undervalued in SaaS. With your success at Robly and Retention.com, how do you handle it, and what metrics do you track?

Adam: It's tricky. At Robly, we did one-on-one onboarding but found one-to-many worked just as well, maybe even better. RB2B is self-serve, so no customer success there. At Retention.com, we added customer success for a complex second product.

We gauge success through feedback, if customers complain or wait too long for help, that’s a problem. We track outreach frequency and ensure issues are resolved quickly. But for us, customer success is more about high-touch support, not upsells or cross-sells. If I can automate it, I will, but some products just need human support.

Activating Users for RB2B

Ani: How do you activate users for RB2B, especially given that your main acquisition channel is organic social? What metrics or KPIs do you track for activation?

Adam: We track the percentage of free signups that collect at least one contact, which indicates they've started using the script. Surprisingly, this number is very high, around 9% conversion from free to paid, while the norm is 1-3%. Even with a basic onboarding flow, this metric has remained strong, showing we're activating users effectively. We’ve adjusted our pricing model to achieve this, and it’s working well. Activation is our strong suit right now, although we have other challenges to tackle.

Investing Insights

Ani: You’ve invested in various startups and funds. What do you look for in potential investments, and how do you support their growth?

Adam: I’ve mostly moved away from investing because I prefer building startups. When I did invest, I looked for experienced founders with strong organic traction leading to revenue growth. 

“I avoid startups with vague metrics and focus on those demonstrating clear, organic growth and a path to actual value.” 

My advisory roles are limited to specific cases where my experience can provide significant value, but I don’t engage in broader investing or company support.

AI's Impact on Marketing and Content Creation

Ani: With AI being a buzzword, how do you think it will change the marketing landscape, and are you exploring AI in your work?

Adam: I believe AI won't replace the personal touch in content creation. While AI can assist with editing and generating ideas, the most compelling content often comes from a personal perspective that AI lacks. For instance, I’ll continue writing my LinkedIn posts because authentic, high-quality content has a significant impact.

We use AI in customer support, where it handles repetitive queries efficiently before escalating more complex issues to human agents. This integration enhances support by leveraging AI’s extensive knowledge base. However, for personalized one-to-one sales, AI's current capabilities don't fully match the nuanced, thoughtful interactions of a skilled salesperson. AI serves as a tool, but human creativity and intuition remain crucial.

Epilogue

Key Takeaway #1: Bootstrapping is a valuable approach that can lead to greater freedom and opportunities.

Key Takeaway #2: Achieving product market fit is crucial for long-term success in startups.

Key Takeaway #3: Acquisition and activation metrics are key to understanding business health.

Key Takeaway #4: Founder-led growth is becoming increasingly important in the current market.

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