At 37, you're actually at a prime age for entrepreneurship. Research from the Harvard Business Review found the average age of successful startup founders is 45, with the highest-growth startups founded by entrepreneurs with an average age of 45-50. Your accumulated experience is an asset, not a liability.
Rather than seeing this as a binary choice between continuing or quitting, consider a third path: being more selective and focused. What if you committed fully to Tillit for 18-24 months with clear milestones and decision points?
Thanks a lot.
I’m going to sit down and define what success looks like for Tillit over the next 18–24 months — in terms of traction, funding, and team growth. But still with the current situations, I don't know, how long can I move.
Would love to know: What kind of milestones or decision points would you recommend for an early-stage marketplace like Tillit that’s solving cash flow and delivery problems for retailers?
Onboard 20-30 retailers consistently ordering through your platform
Establish 3-5 functioning mini-warehouses in one focused neighborhood or district
Achieve 70%+ retention rate (retailers placing second and third orders)
Demonstrate consistent 1-2 day delivery timeframes vs. industry standard
6-Month Milestones:
Develop a simple but scalable credit scoring system for your retailers
Implement a minimal credit offering for your best customers (even if limited)
Create streamlined logistics model that can handle 3-5x your current volume
Document 3-5 case studies showing measurable retailer benefits (time/cost savings)
12-Month Decision Points:
Revenue covering operational costs (excluding your time)
10-15% month-over-month growth in transaction volume
Clear unit economics showing profitability per delivery
At least one key metric where you're 2-3x better than
traditional wholesalers
Rather than trying to fund everything from your agency, consider a "minimum viable credit" approach - perhaps starting with net-15 payment terms for your most reliable retailers, then gradually extending as you validate repayment behavior.
Could you saturate just one neighborhood or product category first to demonstrate density advantages?
The key now is focused execution rather than trying to solve every problem at once. What's the absolute minimum version of Tillit that delivers real value and can grow without significant outside capital?
Thank you, this is something similar to what we have in mind.
And currently, as you told, we are focusing just on perishable bakery snacks, which only have 1 day life. And the credit period for that product is just 1 day. So with that, we are trying to capture 10 shops with in a month, who orders daily.
Just to add — I’m not looking for sympathy or praise. I genuinely want honest advice from fellow builders and thinkers here. If you’ve been in a similar place — hitting walls, pivoting endlessly, with family pressure mounting — what helped you decide to keep going or step away?
Also, if you think there’s a smarter way I should be leveraging my skills or experience, I’m all ears. I’m not married to any single idea — I just want to build something that works and helps people.
Your wife is a gem, putting up with your chasing opportunities with poor market fit.
The essence of business is delivering something that people want so much that they are willing to pay for it.
It appears that with Quadregal (I assume it is the consulting biz you mentioned) you have over 500 successes. Based on the information you have shared it appears to be a successful business.
If you were to stop thinking the grass is greener elsewhere, you might realize that the grass under your feet is already green and with more watering and care it would be the greenest.
Wouldn't you be making even more money than by taking a job if you were to focus your talents and energies upon the business that is already supporting you and your family? Taking agency income to prop-up a capital intensive idea is not honoring your responsibility to your family and your patient wife.
You only need to quit doing what doesn't work and do more of what does.
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.
Working on my first company right now. I would keep pushing. You're doing a great job of a post mortem, but what other aspects do you think you could improve on a day to day.
The "Well I could just work harder" is valid to a point; if you're not putting in enough time it will show. But I think you are since many of these failures are not you "just giving up" which YC tells us is about 60% of startups. So as long as you're constantly improving I think you're heading in the right direction.
Its possible that you never make it, and that is a reality we all must face when starting businesses. But if you have the energy, and you find fulfillment in the work. I would continue.
I don't see any need to "finally" anything. I have done a number of start-ups, enough to retire on though none spectacular, and probably fewer than you depending on how one counts them.
I am doing a PhD part time, and running a few local groups (including the local inventors' club), and keeping some powder dry, ie time and cash on hand and networking, so that if another opportunity arises then I can follow it.
I love the idea of keeping some powder dry — I think that’s a mindset I need to internalize more: pacing myself, staying sharp, and being ready when the right opportunity comes. But at the same time, I'm getting tired, failure after failure and words from my relatives and even from my wife. It's getting super hard. Still I want to move forward.
Nobody can answer these questions for you friend ;-( We are all tragically, inevitably free.
Sine you have to answer them, you need to find out who you are. Good news is that you create who you are every moment, with the decisions you make, the actions you do, the promises you keep--and the promises you break.
In other words, you can find out by just kind of feeling your way.
I will add, listen to these with your wife so you can share a similar vision for your future.
Also, check out the podcast How I Built This podcast with Guy Raz. Hearing the stories of other founders really is inspiring, and my wife and I have found listening to these really helpful thinking about our business.
He talks about exactly this. Has a great line something like "you just want to be able to say I gave it my all and mean it."
If you stop now do you mean it?
I'm a little order, 49 and I recently "gave up" and took a W2 job. But I was definitely done. Could not go on with my make it big ideas one day longer.
At 37, you're actually at a prime age for entrepreneurship. Research from the Harvard Business Review found the average age of successful startup founders is 45, with the highest-growth startups founded by entrepreneurs with an average age of 45-50. Your accumulated experience is an asset, not a liability.
Rather than seeing this as a binary choice between continuing or quitting, consider a third path: being more selective and focused. What if you committed fully to Tillit for 18-24 months with clear milestones and decision points?
Thanks a lot. I’m going to sit down and define what success looks like for Tillit over the next 18–24 months — in terms of traction, funding, and team growth. But still with the current situations, I don't know, how long can I move.
Would love to know: What kind of milestones or decision points would you recommend for an early-stage marketplace like Tillit that’s solving cash flow and delivery problems for retailers?
3-Month Milestones:
Onboard 20-30 retailers consistently ordering through your platform
Establish 3-5 functioning mini-warehouses in one focused neighborhood or district
Achieve 70%+ retention rate (retailers placing second and third orders)
Demonstrate consistent 1-2 day delivery timeframes vs. industry standard
6-Month Milestones:
Develop a simple but scalable credit scoring system for your retailers
Implement a minimal credit offering for your best customers (even if limited)
Create streamlined logistics model that can handle 3-5x your current volume
Document 3-5 case studies showing measurable retailer benefits (time/cost savings)
12-Month Decision Points:
Revenue covering operational costs (excluding your time) 10-15% month-over-month growth in transaction volume
Clear unit economics showing profitability per delivery At least one key metric where you're 2-3x better than traditional wholesalers
Rather than trying to fund everything from your agency, consider a "minimum viable credit" approach - perhaps starting with net-15 payment terms for your most reliable retailers, then gradually extending as you validate repayment behavior.
Could you saturate just one neighborhood or product category first to demonstrate density advantages?
The key now is focused execution rather than trying to solve every problem at once. What's the absolute minimum version of Tillit that delivers real value and can grow without significant outside capital?
Thank you, this is something similar to what we have in mind.
And currently, as you told, we are focusing just on perishable bakery snacks, which only have 1 day life. And the credit period for that product is just 1 day. So with that, we are trying to capture 10 shops with in a month, who orders daily.
Thanks for reading this long post!!
Just to add — I’m not looking for sympathy or praise. I genuinely want honest advice from fellow builders and thinkers here. If you’ve been in a similar place — hitting walls, pivoting endlessly, with family pressure mounting — what helped you decide to keep going or step away?
Also, if you think there’s a smarter way I should be leveraging my skills or experience, I’m all ears. I’m not married to any single idea — I just want to build something that works and helps people.
Thanks again.
Your wife is a gem, putting up with your chasing opportunities with poor market fit.
The essence of business is delivering something that people want so much that they are willing to pay for it.
It appears that with Quadregal (I assume it is the consulting biz you mentioned) you have over 500 successes. Based on the information you have shared it appears to be a successful business.
If you were to stop thinking the grass is greener elsewhere, you might realize that the grass under your feet is already green and with more watering and care it would be the greenest.
Wouldn't you be making even more money than by taking a job if you were to focus your talents and energies upon the business that is already supporting you and your family? Taking agency income to prop-up a capital intensive idea is not honoring your responsibility to your family and your patient wife.
You only need to quit doing what doesn't work and do more of what does.
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.
Working on my first company right now. I would keep pushing. You're doing a great job of a post mortem, but what other aspects do you think you could improve on a day to day.
The "Well I could just work harder" is valid to a point; if you're not putting in enough time it will show. But I think you are since many of these failures are not you "just giving up" which YC tells us is about 60% of startups. So as long as you're constantly improving I think you're heading in the right direction.
Its possible that you never make it, and that is a reality we all must face when starting businesses. But if you have the energy, and you find fulfillment in the work. I would continue.
Appreciate the encouragement — and wishing you the best on your first one! Keep building.
I don't see any need to "finally" anything. I have done a number of start-ups, enough to retire on though none spectacular, and probably fewer than you depending on how one counts them.
I am doing a PhD part time, and running a few local groups (including the local inventors' club), and keeping some powder dry, ie time and cash on hand and networking, so that if another opportunity arises then I can follow it.
I love the idea of keeping some powder dry — I think that’s a mindset I need to internalize more: pacing myself, staying sharp, and being ready when the right opportunity comes. But at the same time, I'm getting tired, failure after failure and words from my relatives and even from my wife. It's getting super hard. Still I want to move forward.
Nobody can answer these questions for you friend ;-( We are all tragically, inevitably free.
Sine you have to answer them, you need to find out who you are. Good news is that you create who you are every moment, with the decisions you make, the actions you do, the promises you keep--and the promises you break.
In other words, you can find out by just kind of feeling your way.
Never stop.
Go listen to all this... https://www.founderspodcast.com/
I will add, listen to these with your wife so you can share a similar vision for your future.
Also, check out the podcast How I Built This podcast with Guy Raz. Hearing the stories of other founders really is inspiring, and my wife and I have found listening to these really helpful thinking about our business.
oh this video is for you:
https://www.youtube.com/watch?v=ZeuRKAsW__E
"How To Know If You Should Work Harder"
He talks about exactly this. Has a great line something like "you just want to be able to say I gave it my all and mean it."
If you stop now do you mean it?
I'm a little order, 49 and I recently "gave up" and took a W2 job. But I was definitely done. Could not go on with my make it big ideas one day longer.
Thank you, I will check.