New Adventures

New Adventures
Photo by Jael Coon / Unsplash

It's been far too long since I wrote anything for my blog. Much of my writing efforts have gone into my substack, CardsFTW. My busy work life has also sapped much of my energy for writing here.

It's once again time for a blog post about starting something.

In 2018 I left Red Ventures (Bankrate/CreditCards), which had acquired my first venture-backed startup, Wallaby Financial. I took a few months off, which I did not really enjoy (it gets boring!), and started Vertical Finance.

At Vertical, we hoped to help smaller merchants with passionate customers build loyalty through rewards cards. Enter COVID-19, etc., etc.; things didn't go as planned. We were able to make a soft landing and preserve options for our investors by selling the company to Apto Payments in 2021.

Apto was a classic startup roller coaster. We were growing and hiring. We raised money. We derailed, had to shrink the company, and eventually, Apto itself was acquired. They haven't updated the website and all, but I am no longer on the leadership team.

After two venture-backed companies, I am returning to my entrepreneurial roots and doing some sole proprietor-style consulting. I recently started Totavi. Through Totavi, I am helping companies of all sizes with their product development, marketing, and general management needs as a consultant focusing on fintech. It is energizing to get to work with several different teams and leverage my 20+ years in technology to help companies move faster and make smarter decisions.

I love working in startups and growing companies. Operating is fun, and I know I have the skills and experience to help founders and leadership teams. I also have learned that I am a better product lead or coach than I am a CEO. I don't have the interest or patience for fundraising and playing the venture capital game myself.

I'm very grateful that I have had the experience of raising money from top-tier venture capital firms on my own and as part of a management team. Pitching Sequoia and the like was a goal of mine, and I can check that off. I'm not sure I had the audacity to believe Sequoia would write me a check (that, in it itself, might be part of my problem.)

With Totavi, I can help companies, participate in startup land, work on some of my own projects (like CardsFTW and more), and depend on my ability to sell services to grow instead of asking for investment dollars.

Will this last? I don't know. Who can say what the future will be? I know many people expect me to start another, more traditional startup. What I know is that for now, this is the best choice for my family and me.

If you need some assistance with building a fintech (or non-fintech product), marketing, or want a startup coach who has been through the wringer, send me a note. I'd love to help!