Wingman Tracker

Founders Ben and Piyush sold Wingman in 2021 to focus on other projects — it's now part of the SureSwift Capital portfolio. You can read more about their exit story in our interview with Ben here: https://www.sureswiftcapital.com/interview-with-wingman-founder-ben-latz/

Not much more to report here - just time and patience. Continuing to provide good customer support and letting the word spread. Operating as a side business for about 30 minutes a day.

We're almost 3 years in since launch, so it hasn't been the fastest growth but nonetheless here we are! Organic growth at 10% a month does start to add up in this MRR territory.

Extended free trial to 30 days instead of 14 days, which seems to be a much better fit for the product. Just like before, it's only been word of mouth in combination with good conversion rates, manageable churn, and very responsive customer support.

Started collecting some more data on feature usage and such, so the next stage of effort will be a combination of improvements via analysis-based decisions and marketing with partnerships and advertising campaigns.

Seems to make sense to consider each $1k kind of a milestone up to $5k, but the next one I have my eyes set on is $10k, so I won't report an MRR milestone until then.

The product is definitely solid enough to increase the flow of people in without me being a bottleneck. So it's been an interesting transition to wrestle with to start focusing more on the business side instead of only refining/tinkering with product (which doesn't impact revenue directly).

As the inflow of word of mouth from some online options trading communities continues, MRR keeps climbing (at about 15% MoM). Half of the trials convert to paid subscriptions.

I've now been adding in some automation software to make things easier, such as Baremetrics (recover, cancellation insights, etc), upgraded Zapier to add on a trial expiration notice email, Honeybadger for error tracking/monitoring, and created a Slack group for subscribers for both social and customer support use.

And for the first time, I started working with a freelance developer to help improve the codebase and integrate a new solution that would improve the product - reinvesting a lot of the revenue at this point.

Up next is paying more attention to marketing, landing page, customer flow/journey, and distribution partners, etc.

We started getting picked up more in option trading communities online because our customers were sharing the link in forums and such. A major help was when a community leader latched onto our product and started sharing it subtly in her content (had to be careful not to cause too much traffic flow, since customer support is still a bottleneck).

And same ol' (no paid traffic, no referral partners, no content). Our focus/efforts are still on other full-time commitments (job or another startup), so effort outside of customer support and product maintenance is minimal.

Wingman up until this point was $25/mo or $250/year, which was really an introductory price, but this was a no-brainer for customers who experience the problem it solves, and it was too low to be sustainable for us to keep working on it given the limited traffic flow.

So, we raised prices to $49/mo and $490/year for new customers, grandfathering in everyone who was already subscribed. This was a very positive change and we receive very little pushback on this price. It also now is a pricepoint that could be viable for referral partners to share revenue.

Just more word of mouth and reduced churn, likely because of our big v2 improvement, which also enabled easier feature development and maintenance.

Over a year in, and still only making $2k/mo for the 1,000+ hours put in so far was underwhelming, but after being much more informed about the SaaS process and others' experiences, it seemed par for the course.

Just hanging in there, keeping things smooth with great customer support, hoping word of mouth keeps doing its thing.

By this time we've still done no paid marketing/advertising, no content marketing, nothing - which is not a recommendation or proud achievement, instead a point to highlight to give some context.

We essentially rebuilt the application to accomplish the following:

1. Rails 4 --> Rails 5 (Rough!)
2. Vue.js frontend, pushed calculations to Vue, and refactored Rails controllers/dataflow to drastically improve performance and user experience.
3. Bootstrap --> TailwindCSS for better custom design and maintainability. This was so tedious, as it was the first time using Tailwind, but so worth it!
4. Yearly Plan and Stripe management panel in Settings to improve cash flow, reduce churn, and reduce customer support touch for billing (reactivations and cancellations mainly).

This really matured the product, as the first version was pretty clunky being full Rails with page refreshes, etc., so it noticeably kicked up word of mouth.

This was driven just by word of mouth and me posting on Twitter. No launch on ProductHunt, Reddit, or the like, given the extremely niche nature of it. No paid traffic either. Just making customers happy with feature improvements and acting on suggestions that we thought were a good addition.

While I don't remember exactly what this felt like, since I'm adding this milestone retroactively in Jan 2020, it was likely a time when we started appreciating how long and slow the SaaS ramp can take. It was discouraging, but as long as we kept things humming along, we assumed word of mouth would continue, and if it didn't, that just meant we weren't doing a good enough job on the product.

Over a year or two, Ben built up a small Twitter following in the retail options trading community and released free spreadsheets to gauge interest in a trade tracking solution, since everyone seemed to struggle with the tedious process of tracking and analyzing their trading.

We (Ben and Piyush) dabbled in the initial creation of Wingman in the latter half of 2017, but started going full nights and weekends in January 2018 when we moved to Chicago after graduating college for our first jobs. We did 100% of the work in-house, which is still true through January 2020 when writing this milestone.

We then launched a landing page to explain the concept and accept early access waitlist sign ups in April 2018. It built up to around 250 people (just from Ben's Twitter) before we opened real signups on June 1, 2018.

We charged from Day 1, offering a 14-day trial and then $25/mo single tier, credit card required.