This is month 8 of my pursuit to bootstrap my own SaaS business. I’ve been full-time on this for the past 8 months. Inspired by mtlynch and others, I’m taking a stab at documenting this journey publically.

The first 7 months #

Retrospective for the Month 1-7 does not exist because I was uncertain if I’d be sticking to this for this long and honestly was embarrassed to fumble publicly. In summary, months 1-7 were more of a rollercoaster than anything else. Slacking off coupled with jumping between new products every so often and engaging with job opportunities occasionally. It was an uncertain period on the whole expedition itself with constant back-and-forth between whether to continue this or go to a job.

Would I say I’ve figured it out now? I think for the most part, yes. Even otherwise, I’ve grown out of the fear of being uncertain publicly, and, if anything I think this phase of the journey where one’s figuring out things or establishing the business is more important and is rarely talked about out there. Most of the “startup” or entrepreneur journey goes like this, “I started this x years ago and here I am making $y” followed by a high-level summary of their journey. It is useful, but then it comes with the survivorship bias and will be very hard to relate for the ones that are just getting started.

For me, when I set out to start this pursuit, there were a lot of unknowns, the most important of them was which product/business to even focus on. I just knew I wanted to make this my full-time work, but didn’t know how or with what. That led me on a loop that went more or less like this,

A new idea -> Start working on that idea -> Nah, more logical to focus on growing my existing products -> Not fast enough progress, maybe I should join a job -> No, Entrepreneurship FTW -> A new idea -> Start working on that idea -> Nah.. and so on

To give you an idea of the times I’ve gone through this cycle, in the last 6 months, I’ve started working on 4 new product ideas, launched 2, and engaged with 5 potential job opportunities (all of them inbound, which just made the uncertainty/figuring out even worse as that’s a potential lost opportunity). It’s not all for loss though, the 2 products I ended up launching are making very small revenues that they can pay for themselves. RosterBird has grown by 40% in revenue during this period as well. But, zooming out I’ve been more or less circling around with little progress forward. If you had read this journey month by month, you would be scratching your head as to why I’m jumping to new things every other month, tbh, I did/do as well.

The last month of this period is when I finally decided to zero in on one product idea and that is RosterBird. That said, if I back out of this again and go on that cycle, I’m hoping these posts here would either act as a deterrent or at the least, force me to deconstruct the decision than just winging it.

I’ll try to publish the month 1-7 when I get a chance or when the current course succeeds so that when I tell the story, that period will look like a “figuring out” phase rather than “slacking off and coasting around” one 😅 .

Enough talk about the yestermonths, let’s come to the present.

Feb 2024 Retro #

Summary #

Finalizing, for the last time, which path to take and the product with which to focus. It was a toss-up between the (yet another) new product (keenly) I’ve been building for the past 2 months or my existing product (RosterBird). Decided to go with RosterBird.

Highlights #

• Paused development of Keenly.
• Doubling down on RosterBird.
• Applied to TinySeed and got a callback.

Deciding between Keenly & RosterBird #

I started off the month with the decision still pending on whether it’s wise to start another product or to double down on the one that’s working. But, being afraid that I’d slack off again if I was not working on something actively, I defaulted to working on Keenly without much deliberation. The loops of the last 7 months with seemingly no progress forward made me anxious to pause things to revisit it. I just steamed ahead.

I was spending 20% of the time on marketing-related stuff and 80% on development. 2 weeks in, I applied to TinySeed for RosterBird on a whim. I’ve been a fan of their content for a long time, and they have a killer mentor list on their roster it was a no-brainer. I wasn’t expecting it to go any further, firstly because there’s usually a good demand for their program and the fact I myself haven’t been working on the product full-time.

But then, a week later I got a call back. It was a follow-up to the application, but it was a confidence boost for me to relook at RosterBird.

This coupled with the shrinking runway and the seemingly lost few months, served as a wake-up call for me to stop and really revisit it. It is suddenly imperative for me to spend my time on the correct product than just fucking around and about.

Once I had permission to look at things, RosterBird came out on top any which way I looked at it. There wasn’t much science to it, it’s a revenue-generating product and is approaching PMF, with good potential. The only path in which Keenly came out on top was “IT’S A SHINY NEW PRODUCT, WEE WEE”.

Jokes aside, it’s clearly the engineer in me that wants to focus on keenly. Because it’s a greenfield product and short-term, I get to code code code without regard for other stuff. Whereas for RosterBird, the immediate next several steps are not engineering, but stuff like marketing, ads, and growth which needs skills outside my expertise. So, naturally, the conservative part of the mind wants to do things that it’s comfortable doing. To my determinant, it’s the engineer side that has dominated decisions for me the last few months which resulted in me starting multiple new ideas without growing/focusing on one.

Just for a double measure, I’ve asked around with my mentors and posted on a couple of forums as well and the consensus of them all is that the smart bet is RosterBird.

I paused the development of Keenly and went all in on RosterBird. Granted, it’s only been a week and I’m still in the beginning of that uncomfortable phase where I’m learning things and charting a course. I’m hoping by next month, I’ll be at a cruising altitude where I’ll have a reliable and repeated process for the non-engineering stuff.

TinySeed #

As mentioned before I’ve been a big fan of them for many years. I applied with RosterBird about 2 years ago but didn’t get in as they had a revenue cut-off I couldn’t make. This time around, I applied on a whim and to my surprise I got a call back from their EMEA program director.

It’s mostly a follow-up from my application and other questions along the same lines and some legal stuff, that’s about it. I don’t think it is any indication of being closer to acceptance than before. That said, it was very exciting to get that acknowledgement.

Goals for March #

• Update the marketing pages to make language consistent and clear
• Pricing changes - Reduce the Trial period and make pricing less confusing
• Gather testimonials from my existing customers