Introduction
Sreenath: Building an Amazon agency business or retail media agency business, running it for several years and exiting successfully is no small feat. And today I have someone who has done exactly that. Kiri Masters was the founder and CEO of Bobsled Marketing. Kiri, thank you for joining me.
Kiri Master: Thank you so much. Great to be here, Sreenath.
Sreenath: I have to add that besides running a successful business during that time, she has accumulated some impressive credentials. If you don't mind, Kiri, I'm going to just share a few.
Kiri Master: Go on.
Sreenath: AdAge named you as an Advertising Changemaker, 40 Under 40. I think that was back in 2022. You've been named one of the top 100 retail experts by Rethink Retail for the past three years. You've also co-authored and published multiple books. I actually bought Amazon for CMOs and read it a while back.
Kiri Master: Cool. Thank you.
Sreenath: That's just a small list. I'm sure I've missed a bunch, but your journey is both inspiring and impressive. I've been meaning to do this for a while. I'm so happy you joined us and hopefully we can get a little bit deeper into your entrepreneurial journey.
Kiri Master: Yeah, sounds great. Happy to share. I always love talking about this stuff.
Sreenath: Where are you, by the way? You're clearly a world traveler. Where are you?
Kiri Master: Right now, I'm in Perth, Western Australia, where I'm originally from. But you're right, I have been doing a lot of travel over the last year. I'm looking forward to getting back to Atlanta, where we had a home base for a couple of years, and settling down and not flying around too much for a little while.
How It All Started
Sreenath: I want to talk about your new gig or gigs later in our conversation. But let’s start with your entrepreneurial journey. What was the moment you decided, “I'm going to start a business”?
Kiri Master: Bobsled was my second business, but it quickly became the more successful one. I started a little e-commerce business on the side of my corporate banking job at JPMorgan Chase in New York City.
Sreenath: JPMorgan Chase? That’s where you were?
Kiri Master: Yeah, I was working in corporate strategy, and I started this little business on the side selling lamp-making supplies. I started on Etsy and WooCommerce, and then eventually got into Amazon. It was a very small business, never got that exciting, but it gave me a front-row seat to marketplaces, especially Amazon. I later moved into a business banker role, working with small business clients. After talking with a few of them who sold on Amazon, I realized I knew more than they did. I found myself giving them advice. That’s when I thought, “Maybe I could be an Amazon consultant.” I left the corporate job, and I was thrilled. I still remember leaping out of bed every day. I made no money the first year, but it was terrific.
Early Days at Bobsled
Sreenath: You started helping the people you were talking to. What were you doing for them—strategy, operations?
Kiri Master: This was 2015, so it was a lot simpler back then. We helped brands launch new products. The ad capabilities were limited—just auto or manual campaigns for Sponsored Products. We helped small brands set up their catalogs and launch on Amazon.
Sreenath: Was Bobsled always just you as the founder?
Kiri Master: Yes.
Sreenath: Did you raise capital?
Kiri Master: No, it was bootstrapped.
Reflections on Growth
Sreenath: Walk me through a time where you thought, “What am I doing?” Or was it always clear this is what you wanted?
Kiri Master: That’s the thing about being an entrepreneur—it's clarifying. You just take the next step. It might be something exciting or it might be putting out a fire with employees or clients. But there’s always a clear “next.” After I exited, I realized how simple that clarity was. It wasn’t easy, but it was simple.
Sreenath: How big was the team by the time you exited?
Kiri Master: I think 30 or 40 people when we sold in 2022.
Sreenath: That kind of growth, while running day-to-day operations, is hard. How did you balance working in the business vs. on the business?
Kiri Master: Three things: timing, content, and team. I got into Amazon in 2015, which ended up being the perfect time. I didn’t know it then. Content was our growth engine. I had no money, no network. But I had time and fingers. I wrote blog posts, made tutorials, courses—just hustled with educational content. And the third thing was the team. I lucked into finding Julie Spear, who became my integrator. She was our first hire and ended up running the whole company. EOS helped us structure the org effectively.
Content as the Engine
Sreenath: I want to talk more about content. Would you say content was your founder edge?
Kiri Master: Yes, 100%. That was the edge.
Sreenath: For other agency founders, what’s the secret to making content work over time?
Kiri Master: Cadence is important. A lot of people start podcasts—most stop after 7 episodes. No one listens at first, and it’s hard psychologically. The other big challenge is fear—fear that you’ll say something dumb, get judged, get canceled. I still feel that way, but I push through it.
Sreenath: I relate to that. You don’t need a million followers. Even 10 or 20 is enough to start. It builds. What helped me was realizing no one’s watching at first, which gave me freedom to experiment.
Kiri Master: Exactly. And honestly, most content is boring. People play it safe. There’s no point of view. They don’t share proprietary knowledge or real takes. It just doesn’t land. If you’re going to do it, do it with passion.
From Startups to Mid-Market
Sreenath: Let’s talk about inflection points. What were some of the step-function moments in Bobsled’s growth?
Kiri Master: A big one was shifting from startups to mid-market brands. We moved from performance-based to retainer pricing. That required more confidence. Another shift was toward enterprise brands later in the journey, which brought new sales processes and expectations.
The Exit
Sreenath: Let’s talk about the acquisition. Was it planned or serendipitous?
Kiri Master: I spent 18 months agonizing over it. My husband finally said, “Just decide.” I had two paths: hire a CEO or sell. Hiring a CEO would take time and I'd still have to be involved. I chose to sell. I hired an M&A advisor in mid-2021—great timing. We closed in 8 months.
Sreenath: How did you choose the banker?
Kiri Master: My fractional CFO urged me to find someone who understood the agency world. I was about to hire someone with a generic “spray and pray” buyer list, but I ended up hiring two guys who had bought agencies for decades. It made all the difference.
Sreenath: What influenced the valuation beyond the obvious?
Kiri Master: Our brand. A lot of acquirers knew us. Our content, visibility, and relationships played a big role. I always say—be friendly with your competition. You never know where opportunities come from.
What’s Next & Looking Forward
Sreenath: Would you start the same business again today?
Kiri Master: Absolutely not. It’s way too competitive. Timing matters. If I started now, it would be something around TikTok or retail AI infrastructure.
Sreenath: Looking ahead five years, what big changes do you see?
Kiri Master: AI agents will do our shopping. They’ll price-shop, generate baskets, render visuals. You’ll interact with them visually—try on clothes, preview haircuts. Retailers will need to plug into these agents. That’s a massive opportunity and challenge.
Closing
Sreenath: What are you working on now?
Kiri Master: I run a daily podcast and newsletter called Retail Media Breakfast Club. It’s a 10-minute download of what’s happening in the space.
Sreenath: Final advice for agency founders?
Kiri Master: Get out of your bubble. Competitors can be collaborators. Relationships matter more than most people realize—especially when it comes to M&A.
Sreenath: This has been incredible. Thanks for joining me, Kiri.
Kiri Master: Thank you so much. Great to be here.