Thanks for this perspective — truly appreciate your honesty. You’re right in pointing out that my wife has been incredibly patient and supportive through all this. I’m lucky there.
And yes, Quadregal has indeed been my safety net all these years. I’ve always seen it as a fallback, not the main bet — but maybe I’ve been undervaluing the fact that it has delivered consistently. I guess I got caught up in chasing bigger “startup-style” wins and forgot that there’s real value (and freedom) in growing something that already works.
That said, I still feel there’s something powerful in Tillit’s core idea — but you’ve made me realize that I need to draw a line between ambition and recklessness. Maybe there’s a middle path: treat Tillit like a disciplined side venture (with clear boundaries), and double down on growing Quadregal with the same energy I pour into these “new” ideas.
Thanks again for the much-needed reminder Would love to hear how you’ve approached similar crossroads, if you’ve faced them.
I appreciate you responding to my comments. Rarely do I get any responses from the person originally posing the question.
I got involved in my first startup soon after I graduated with my undergrad degree and started on a part-time masters degree. I worked on a day job to pay my rent, food, etc. And I worked for the startup the rest of the time. Sometimes I would work all night and go to the day job without any sleep, just a quick shower. It didn't work out. The startup did a pivot and in so doing screwed me out of at least a million AUD. That was lesson #1. It was decades ago.
I have since been involved in many other startups, most on a full-time basis. Varying durations until runway got burnt up. I'm very much the tech guy. In hindsight I put too much faith in the business acumen co-founders and investors. Had to return to consulting work in between those startup attempts. That is how I kept myself afloat.
I'm in Australia and VCs are nothing like those in SV. In general risk aversion is high and the success dynamics in the USA don't translate well to local conditions, culture, etc. I think you may be in a comparable environment. So you need to temper your expectations for Tillit in light of your local environment. Read up on Steve Blank https://steveblank.com/books-for-startups/ The takeaway: find product market fit. If you don't you don't have a business.
I have gone on to get my PhD in software engineering and from time to time I teach at one Australia's best universities. I'm now retired courtesy of some good real-estate investments. I learnt a lot about the business world through consulting work. I now focus technical mentoring for startups on behalf of the investors rather than the founders.
And yes, Quadregal has indeed been my safety net all these years. I’ve always seen it as a fallback, not the main bet — but maybe I’ve been undervaluing the fact that it has delivered consistently. I guess I got caught up in chasing bigger “startup-style” wins and forgot that there’s real value (and freedom) in growing something that already works.
That said, I still feel there’s something powerful in Tillit’s core idea — but you’ve made me realize that I need to draw a line between ambition and recklessness. Maybe there’s a middle path: treat Tillit like a disciplined side venture (with clear boundaries), and double down on growing Quadregal with the same energy I pour into these “new” ideas.
Thanks again for the much-needed reminder Would love to hear how you’ve approached similar crossroads, if you’ve faced them.