Opening up about the past few years

Back in September 2014, I quit my job to start my first company. What ensued was an exhilarating and humbling roller coaster of an experience — more on the specifics of that later.
But first, about this blog: it began as a private journaling exercise that a fellow first time founder had recommended. It helped me reflect on how I felt, what I learned, and what I’ll do differently next time around. I have always enjoyed writing, but this was the first time it’s been this impactful for me, personally.
Since I wasn’t always forthcoming about my experiences during the journey, I’m going to share what I’ve journaled about in a series of forthcoming short posts — so if we’ve lost touch or grown apart over the past few years, my hope is that this can serve as a starting point for reconnecting and picking up where we left off.
Most of my focus will be on the mistakes that I’ve made and what I’ve learned from them — I won’t get into specifics about the company’s journey, though I’m happy to expand on that separately (TLDR: it was acquired, but it largely failed).
Since taking a break from the craziness of doing a startup about a year ago, I’ve been running the product team at Arena, where predictive analytics, Enterprise B2B SaaS, and healthcare have each been new areas of growth for me. In a future post, I’ll expand on my personal struggle with transitioning from founder back to employee. But looking back, I couldn’t have asked for a better 2018 — a year of reflection and personal growth for me.
Below is a preview of the topics that I’ll post about, each being short enough to read in a few minutes. Keep an eye out for my first post about emotional highs and lows and I hope to be in touch soon!
- Opening up about the past few years
- Emotional highs and lows
- Overrated work experience
- All “startup ideas” suck
- Persevere vs. Pivot?
- Mismanaging doubt
- Good Investor, Bad Investor
- How to lose a cofounder
- How to get schooled during an acquisition
- Gotta stop and smell the roses
- Desperation’s effect on decision making
- All startup ideas suck (Part II)
- “Second-time-founder syndrome”
- Transitioning from founder back to employee
- Every idea I’ve ever worked on
- 10 principles for new startup projects
- Gratitude

