⚡️ Founder Diaries Vol 1 Ch 6: Macgill Davis, Founder of Rize - From Raising 3M to Building a Bootstrapped Profitable Business
We celebrate the unfiltered BTS stories of today’s founders - from their highest highs to the lowest lows and how they powered through it all… or didn’t.
😊 Welcome to Volume 1 Chapter 6 of Founder Diaries. Now, Why Founder Diaries?
In an era where founders’ lives are glamorized and their stories are romanticized narratives of seemingly endless success, the behind-the-scenes reality of the highs and lows of being a founder often don’t come to light.
Alongside the startup with a high valuation is the string of risky decisions, maxed-out credit cards, and grueling late-night chats.
Alongside each polished story, there are real challenges, unsung heroes, and unique highs & lows that make every second of the founder's journey worth it. Or maybe not? We will let you decide.
These are the true, unfiltered short stories behind the founders of today. Enjoy :)
👋 Introducing Macgill Davis, Founder of Rize: From Raising 3M to Building a Bootstrapped Profitable Business
Rize is an AI productivity coach that uses time tracking to improve your focus and build better work habits.
For my co-founder Will and I, the path to creating a profitable startup was one filled with emotional highs and lows, multiple pivots, and unwavering determination.
It started at a company called Peer, where I met Will and other talented engineers like John Li of Vimcal.
We had an idea around how we could improve on a really successful feature we had built at Peer, a tool that builds efficient and high-quality communication without endless meetings. So we left Peer to start our first company called Humble Dot. We were getting strong organic growth initially with Humble Dot among tech companies in SF.
Those beginning days felt full of potential and opportunity. We quickly raised a $500k pre-seed in 2017 then $2.6M seed from excited investors and grew our team to 10 people.
I remember feeling like the sky was the limit.
But over the next couple years, we struggled desperately to gain traction and convert users into paid customers. We tried everything to spur growth—enterprise sales, self-serve models, different marketing channels—but nothing seemed to work. As technical founders with no prior experience, that year was like a crash-course MBA in growth. We gave it our all, but couldn't find the one breakthrough we needed.
By early 2020, it was painfully clear we weren’t hitting the metrics needed for our Series A. With little runway left, we made the difficult decision to shut down Humble Dot. Letting everyone go was probably the lowest, lowest point. You're recruiting talented people to take a bet on you, and you care about them.
Having to tell our amazing team that we were winding down the company was absolutely the lowest emotional point for me.
For 6 months, I dealt with the emotional fallout and lack of identity that comes after pouring years into a failed startup. As founders, your work becomes so tied to your identity. After shutting down, Will and I had no money, no team, and no sense of purpose. We had spent years pouring our blood, sweat, and tears into this dream that ultimately failed.
Seeing our friends at Twitter get extremely wealthy from the tech boom while we were broke and defeated - yep, that was hard. We were truly genuinely happy for them, but we couldn't help feeling like we had missed out on that opportunity.
I remember feeling embarrassed to tell people that Humble Dot was done.
The light at the end of the tunnel? During that time, Will and I started testing the idea for Rize - a time-tracking and productivity tool. Despite pushback initially from investors about it being a consumer app, we were determined to bootstrap it ourselves starting in September 2020.
There were many moments of doubt, wondering if this was the right decision or if we were just building something that would only make $60K in revenue. But we persisted through the lean times, pushing forward, one step at a time, each moment we got positive feedback and metrics.
We believed in the vision for Rize and kept seeing glimmers that it could work, even if growth was slower without venture capital.
We started working on the product in September 2020 and launched publicly on Product Hunt in May 2021. In January 2022 we started to really see growth, then we hit profitability in May 2022. We’ve been growing pretty comfortably since then. It’s been a sliding scale of profitability because we have been lucky enough to be able to increase our salaries and we were the only two working on the company until recently.
That was definitely the highest high for us as founders - having a fast-growing, successful true business that we basically bootstrapped.
The profit gave us a new sense of freedom. Now we no longer have this ticking time bomb of needing to raise in 6 months or the company is done. We can build the right way and think long-term.
Will and I have this joke that we actually don't celebrate anything until 6 months later because we've experienced so many things that we thought were going to go through that didn’t work out.
For example when we celebrated too early on how fast we were going to grow. That “great new go-to-market channel” that was working so well ended up drying out a lot quicker than we thought. I feel like I haven't had the high with Rize yet. There's highs that I haven't fully celebrated because I’m still traumatized thinking something isn’t going to happen yet so I can’t celebrate.
Rize is the third company I have started in my life, and I'm very proud we have a fast-growing, successful, true business now, which is a new experience for me.
-Macgill Davis
Learn more about Macgill Davis and Rize below:
If you know someone with a unique founder story who would like to share their BTS journey of founder life - the highest highs and the lowest lows - please feel free to refer them at diariesfounder@gmail.com.
— Michelle Kwok & Christine Lu Hong (The Founder Diaries Team)