Should you start a side hustle? Should you quit your day job and go all-in? Or is it time to sell? Here’s your chance to ask two bootstrapped Founders who’ve been through it already.  

It’s the norm for bootstrapped Founders to flux between working on their products as a side hustle, and working on them full-time over the lifecycle of the product.

Bootstrapped businesses often start as side projects out of necessity. Once a project hits a certain level of profitability, maybe you decide to go all-in to focus on maximizing growth. Down the road, maybe you want (or need) to work full-time on a different project of your own, or an opportunity comes up with someone else that you’re really excited about.

These are all phases in the Founder journey. Wherever you happen to be in yours, we think you’ll want to hear from Wingman Co-Founders, Ben Latz and Piyush Puri

The pair started Wingman — a SaaS that helps options traders track their trades automatically — shortly before graduating from Carnegie Mellon in 2017. After graduating, they both got full-time jobs but kept working on the business together on evenings and weekends. In 2018 Ben left his day job and went full-time on Wingman, but then another entrepreneurial opportunity with a friend came up that seemed like it had a bigger potential upside, and Wingman was in hustle-mode again the following year. 

Eventually in 2021, even though they had built the business to be easy to run, they were ready to sell, book the win, and move their time and energy to other endeavors. 

If you love a good bootstrapped story as much as we do, we’re hosting a free, live AMA (“Ask Me Anything”) style webinar with Ben and Piyush on October 13 at 3 pm CST to talk about their experience building, maintaining, and selling a side hustle. So bring your questions and save your seat! 

Join us for a free, live AMA (“Ask Me Anything”) on side hustles with bootstrapped Founders Ben Latz and Piyush Puri of Wingman hosted by Chris Reedy, VP of Acquisitions at SureSwift.

October 13, 3 pm CST

We’ll talk about: 

  • How to optimize a side hustle if you have a full-time job or other projects
  • Tips for finding a technical Co-Founder for your side hustle
  • Advice for listing a side hustle on a marketplace to sell it
  • Navigating a sale as Co-Founders
  • And more! 



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