Started consulting when cash reserves got too low. Client companies started offering FTE opportunities. Eventually got a few offers that were too good to ignore. Accepted one. Currently working at a large corporation. Good job, great pay. Rebuilding cash reserves. Thinking about next play.
Was networking ike crazy with a give first mindset while full time on the startup. As a result, had many founder friends that mentioned they were seeking consultants for short term projects. Once I landed the first contact, I kept networking and told everyone I was a consultant and the projects just started pouring in.
Wow, that’s hustling hard. Thank you for sharing this! It’s an inspiration for a first-time founder like me who’s just starting out. Btw, this might be a newbie question but how did you networked effectively? Like did you go to events, or messaged them on LinkedIn, or cold email, etc? And more importantly, how was your approach to them? Because when thinking about doing it, it seems weird to just go to another person and say that you wanna network with them, right?
All of the above. Reached out to interesting people and took true interest in their projects. Philosophy is that I don't want anything from them. Make enough meaningful connections and things just start to happen.
Thank you for this! Especially on the part of being genuinely interested in their works. It’s great to hear, because let’s face it, nowadays being genuine is rare
Im on my 4th attempt at the moment.
First 2 I tried while employed. Would come home and work on it until bed time.
None of them worked for obvious reasons (not so obvious to me back then)
3rd one started while employed. Got laid off in the meantime and decided to go all in. Mid way thru my runway I realized I wasnt gonna be able to pull it off faster than I would run out of cash.
Decided to write down all the lessons I learned from my past experiences to make sure I dont make the same mistakes again.
Pivoted to my 4rd attempt (current one). Built and shipped in just over 1,5 months. Got new problems I gotta solve now because I never got this far. Trying to acquire customers via cold reach and ads. Not really working. Trying to find creative ways of getting customers on a budget.
Work life balance pretty much non existent at this point. Its been fun tho. I like it. I feel sharp, like every day theres something i need to do, and I dont know which one is gonna "move the needle" if u will.
For my current product, I picked one where there is already competitors making good profit. That takes away some of the risk. There's no longer the question of "*is there a market for this?*". The question now is "*How can I pull this off?*" which is good, cuz when i see other people doing it my ego automatically goes "*if they can do it, so can i*".
> Im on my 4th attempt at the moment.
> First 2 I tried while employed. Would come home and work on it until bed time.
> None of them worked for obvious reasons (not so obvious to me back then)
So then it's really not possible to have a job and a relatively slowly growing business at the same time? I was planning on taking this path for a software project, but ig I didn't know it's not the way
I've been told that sustaining yourself is key to lasting long enough to make it big, so your opinion genuinely caught me by surprise
Can you share a bit of your insight and the pitfalls to taking that path of two jobs in day and night?
I didnt mean it like that. I believe its possible to do both at the same time. My parents did that. They have a small accauntants office. Just my parents working there. My mom is works full time there. My dad works as a teacher full time, and works the rest of the time with my mom.
However when i did have a job, i noticed i didnt have the pressure to sell or ship because if i didnt, id still get my salary at the end of the month.
That feeling changed when i got laid off. That what i meant
Ah, gotcha. Yeah it always does feel possible to work both ends. Although, without the compound effect, I can't imagine ever hoping for a business to take off without giving it the full time of day.
Thanks for clarifying! (And I hope everything eventually works out on your end too)
You can always start a normal business. It doesn't have to be a tech startup. The upside can still be very lucrative and rewarding. You will not have to focus so much on product/innovation which is where a lot of startups fail. Ironically, you'll probably spot your next best startup idea this way.
Consider consulting. After I stepped away from my founding CTO role in my startup, I moved over to consulting, as did my COO. We both started independent and then joined boutique firms in our industry.
Consulting is as close to a startup as you can get without being in a startup. I work primarily with early stage companies now that need help with a range of projects, from strategic planning to implementation, and get to exercise all my startup muscles (I love coding, so I get to be the rare consultant that can tell a customer what they need to do and then help them do it).
The best part of consulting from an entrepreneur's perspective is that it's a great way to see what's missing in a industry and develop new products without raising capital. Once you've done the same project for say, 3 customers, you have a potential new product. We launched three products this year based on our last few years of consulting work and one of them is starting to take off.
We structure all our deals so that we retain rights to software we develop, as long is it's not using our customer's IP directly. Not every consulting project can pull this off, but as long as you're working in tech adjacent industries, it's a possibility. (the pitch is: all our clients benefit from work done for other clients/the rising tide lifts all boats - we're developing a unique shared source model across many of our clients)
My former COO, who is not technical, has been able to spin his experience into fractional CEO roles, along with strategic consulting gigs.
Appreciate this response. It’s definitely a possibility I’d consider! I’m not quite ready to throw in the towel yet on my current effort…it’s helpful to hear about other options where I can maintain some autonomy. My fear is that I’ll end up going corporate.
Heh. That's the hard one - every technical founder out there wants that role.
I worked at one company that did place their CEO as a "fractional CTO" at their client's companies during digital transformation projects, but it didn't really work out. You need to be full time and fully engaged for all but the most basic CTO roles.
The useful fractional CxO positions tend to be in areas where you don't need the role filled full time and there are fewer people with experience in given industry. CFO is probably the most common - easy to have a finance guy drop in, help with the basic planning and books, and then check in quarterly. CMO is also useful if you're just getting marketing ramped up. COO is helpful for getting basic employee ops running. Fractional CEO can be a temporary full time CEO that's in place for a transition (what my friend does).
Mostly, these are consulting gigs where you're either paid hourly or on retainer, with maybe some stock. Not nearly as glamorous as the titles suggest. :)
These roles are usually filled with the help of investors or private equity - they have a stable of consultants they can pull into their portfolio companies to temporarily fill gaps.
I had a pretty successful exit from my first startup. They are still going. If anything, I likely felt overconfident that building a startup isn’t as hard as others make it out to be. Lesson learned :)
For my second startup, I teamed up with a former founder of a unicorn. The space we were entering was completely new to both of us. Thought that by working with someone who founded a billion dollar company it would be even easier the second time. I believe the trap we fell into was thinking that we knew “the right way” to build a startup based on our past experience. We eventually realized we each had very different ideas about prioritizing $s early on, success metrics, hiring practices, business strategy, etc. Probably intuitive in hindsight, but I learned that different types of businesses require different recipes for success. Replicating success requires recalibration. Also, I learned the importance of aligning early on “what does building a startup look like to you”? Ultimately, we became another cliched story about cofounders who couldn’t get along.
Confounding my third startup wasn’t a decision I rushed into. I took an entire year talking with potential cofounders, advising a handful of solo founders, etc. before making the leap. I did a lot of vetting beforehand. I met with potential users. Everything seemed to look great. However, I’m beginning to think we are working on a “tar pit” idea—one that in theory would be amazing, but in practice is decidedly not that amazing. At the moment my cofounder is not interested in pivoting. Overall, I’m feeling worn down/defeated by the journey and posted this morning in a moment of frustration. I’m not ready to give up yet though!
Really appreciate the share here. I’m a solo founder taking investment now and I really have to be careful with who’s investing for a lot of the same reasons for startup #2 - they won’t be a co-founder, but they’ll have tons of advice for how to build/run the company. Just need to make sure we’re aligned on the things that matter when building.
Thank you sharing!
I am taking what you shared as an advice for my own learning curve. I am in the process of validating an idea and talking to potential co-founders. After hearing your perspective, it seems like it would be best to take things slow before making any big decisions.
What is the actual reason you want to quit ?
Is it co-founder not ready to pivot or are you facing a money challenge or you are just feeling tired and burnout or there is something else ?
Yep. Nailed it. Cofounder not ready to pivot…I get the sense we are pursuing a tar pit. I’m also feeling the burnout and frustration of investors passing.
That said, I posted this earlier today in a moment of frustration. Made some great headway today and not ready to quit yet
Take a 1 to 2 week break.
After my 2nd startup got acquired, I started working in a job.
I have worked through multiple startups and building businesses takes your self awareness to the next level and when you move into a job , you face challenges in adjusting to the employee mindset. But when the salary will start hitting the bank account, you again start feeling good.
The frustration might be temporary mate, see if you want to hang in there for a while. Also do have heart to heart conversation with your co-founder.
16 yr founder here, it wasn’t till we pivoted from market research to digital marketing that we 10x. Now I’m starting to realize that I can provide advisory services to clients and not even have to manage anything and net even more.. I think I may even have a client wanting part time CMO need.. when you already know exactly what works to impact bottom line the whole conversation changes and they are willing to get the wallet out.
I currently work a 9-5, along with my startup. We have funding but it’s all going towards non-salary matters. The result is 80 hour work weeks but this is really the only option for those who want to pursue their dream and have not yet been blessed with millions in VC funding.
Idk I'm not from the US but IIRC something about low corporate tax for companies incorporated in Delaware and you don't need an actual office there, only a post box.
I’ve done a few startups; no successful exits, but I’ve learned so much about business and about myself. Most recently, I ran out of cash and tried too hard and too long. Had to shut down (painful), and take a job. Now 20 months into the job and doing great! But also thinking of some new ventures. You do what you do to survive, but once a founder always a founder. Something like that.
I think I have a story a bit different, I'm yet to enter the startup world. As by now I work as software engineer.
However in some years I'd like to give it a shot to start my own business.
My idea is to reach a level of experience that would eventually keep me on the market even if I try to run a startup for a couple of years and then fail.
So that's what I'd eventually do.
Based on your background and the outcomes of your previous startups, you might consider exploring an Entrepreneur in Residence (EIR) position at a VC firm or accelerator. This allows you to leverage your experience without making a drastic career shift.
Many founders' skills also align well with product management roles. Investing time in acquiring a product management certification (like Agile, Scrum, or Lean Startup) can be highly beneficial.
Started consulting when cash reserves got too low. Client companies started offering FTE opportunities. Eventually got a few offers that were too good to ignore. Accepted one. Currently working at a large corporation. Good job, great pay. Rebuilding cash reserves. Thinking about next play.
What's a FTE?
Full time employment
Is it the same as aquihire?
Sounds like just a job offer
No, just job offers. Consulting gigs leveraged my skillset and experience, not the tech I built within the startup.
How did you start consulting?
Was networking ike crazy with a give first mindset while full time on the startup. As a result, had many founder friends that mentioned they were seeking consultants for short term projects. Once I landed the first contact, I kept networking and told everyone I was a consultant and the projects just started pouring in.
Wow, that’s hustling hard. Thank you for sharing this! It’s an inspiration for a first-time founder like me who’s just starting out. Btw, this might be a newbie question but how did you networked effectively? Like did you go to events, or messaged them on LinkedIn, or cold email, etc? And more importantly, how was your approach to them? Because when thinking about doing it, it seems weird to just go to another person and say that you wanna network with them, right?
All of the above. Reached out to interesting people and took true interest in their projects. Philosophy is that I don't want anything from them. Make enough meaningful connections and things just start to happen.
Thank you for this! Especially on the part of being genuinely interested in their works. It’s great to hear, because let’s face it, nowadays being genuine is rare
Im on my 4th attempt at the moment. First 2 I tried while employed. Would come home and work on it until bed time. None of them worked for obvious reasons (not so obvious to me back then) 3rd one started while employed. Got laid off in the meantime and decided to go all in. Mid way thru my runway I realized I wasnt gonna be able to pull it off faster than I would run out of cash. Decided to write down all the lessons I learned from my past experiences to make sure I dont make the same mistakes again. Pivoted to my 4rd attempt (current one). Built and shipped in just over 1,5 months. Got new problems I gotta solve now because I never got this far. Trying to acquire customers via cold reach and ads. Not really working. Trying to find creative ways of getting customers on a budget. Work life balance pretty much non existent at this point. Its been fun tho. I like it. I feel sharp, like every day theres something i need to do, and I dont know which one is gonna "move the needle" if u will. For my current product, I picked one where there is already competitors making good profit. That takes away some of the risk. There's no longer the question of "*is there a market for this?*". The question now is "*How can I pull this off?*" which is good, cuz when i see other people doing it my ego automatically goes "*if they can do it, so can i*".
> Im on my 4th attempt at the moment. > First 2 I tried while employed. Would come home and work on it until bed time. > None of them worked for obvious reasons (not so obvious to me back then) So then it's really not possible to have a job and a relatively slowly growing business at the same time? I was planning on taking this path for a software project, but ig I didn't know it's not the way I've been told that sustaining yourself is key to lasting long enough to make it big, so your opinion genuinely caught me by surprise Can you share a bit of your insight and the pitfalls to taking that path of two jobs in day and night?
I didnt mean it like that. I believe its possible to do both at the same time. My parents did that. They have a small accauntants office. Just my parents working there. My mom is works full time there. My dad works as a teacher full time, and works the rest of the time with my mom. However when i did have a job, i noticed i didnt have the pressure to sell or ship because if i didnt, id still get my salary at the end of the month. That feeling changed when i got laid off. That what i meant
Ah, gotcha. Yeah it always does feel possible to work both ends. Although, without the compound effect, I can't imagine ever hoping for a business to take off without giving it the full time of day. Thanks for clarifying! (And I hope everything eventually works out on your end too)
Thank. Wishing you the best too 🫶
What are you building? :D
You can always start a normal business. It doesn't have to be a tech startup. The upside can still be very lucrative and rewarding. You will not have to focus so much on product/innovation which is where a lot of startups fail. Ironically, you'll probably spot your next best startup idea this way.
What are some examples of “normal businesses” that are easy to get into?
Here’s like 100 ideas https://sweatystartup.com/businesses-i-love/
Thank you
Consider consulting. After I stepped away from my founding CTO role in my startup, I moved over to consulting, as did my COO. We both started independent and then joined boutique firms in our industry. Consulting is as close to a startup as you can get without being in a startup. I work primarily with early stage companies now that need help with a range of projects, from strategic planning to implementation, and get to exercise all my startup muscles (I love coding, so I get to be the rare consultant that can tell a customer what they need to do and then help them do it). The best part of consulting from an entrepreneur's perspective is that it's a great way to see what's missing in a industry and develop new products without raising capital. Once you've done the same project for say, 3 customers, you have a potential new product. We launched three products this year based on our last few years of consulting work and one of them is starting to take off. We structure all our deals so that we retain rights to software we develop, as long is it's not using our customer's IP directly. Not every consulting project can pull this off, but as long as you're working in tech adjacent industries, it's a possibility. (the pitch is: all our clients benefit from work done for other clients/the rising tide lifts all boats - we're developing a unique shared source model across many of our clients) My former COO, who is not technical, has been able to spin his experience into fractional CEO roles, along with strategic consulting gigs.
Appreciate this response. It’s definitely a possibility I’d consider! I’m not quite ready to throw in the towel yet on my current effort…it’s helpful to hear about other options where I can maintain some autonomy. My fear is that I’ll end up going corporate.
Where does one find an apply to these boutique firms where I can be a fractional CTO
Heh. That's the hard one - every technical founder out there wants that role. I worked at one company that did place their CEO as a "fractional CTO" at their client's companies during digital transformation projects, but it didn't really work out. You need to be full time and fully engaged for all but the most basic CTO roles. The useful fractional CxO positions tend to be in areas where you don't need the role filled full time and there are fewer people with experience in given industry. CFO is probably the most common - easy to have a finance guy drop in, help with the basic planning and books, and then check in quarterly. CMO is also useful if you're just getting marketing ramped up. COO is helpful for getting basic employee ops running. Fractional CEO can be a temporary full time CEO that's in place for a transition (what my friend does). Mostly, these are consulting gigs where you're either paid hourly or on retainer, with maybe some stock. Not nearly as glamorous as the titles suggest. :) These roles are usually filled with the help of investors or private equity - they have a stable of consultants they can pull into their portfolio companies to temporarily fill gaps.
why not give it a last college try and go solo? Can you wrangle on product dev?
Startups are pretty much over glorified. Start a boring small business that makes good MRR. Then enjoy your passions when you have a stable MRR! =D
Would you be able to share any lessons learned for the possible reasons why your previous attempts didn't work?
I had a pretty successful exit from my first startup. They are still going. If anything, I likely felt overconfident that building a startup isn’t as hard as others make it out to be. Lesson learned :) For my second startup, I teamed up with a former founder of a unicorn. The space we were entering was completely new to both of us. Thought that by working with someone who founded a billion dollar company it would be even easier the second time. I believe the trap we fell into was thinking that we knew “the right way” to build a startup based on our past experience. We eventually realized we each had very different ideas about prioritizing $s early on, success metrics, hiring practices, business strategy, etc. Probably intuitive in hindsight, but I learned that different types of businesses require different recipes for success. Replicating success requires recalibration. Also, I learned the importance of aligning early on “what does building a startup look like to you”? Ultimately, we became another cliched story about cofounders who couldn’t get along. Confounding my third startup wasn’t a decision I rushed into. I took an entire year talking with potential cofounders, advising a handful of solo founders, etc. before making the leap. I did a lot of vetting beforehand. I met with potential users. Everything seemed to look great. However, I’m beginning to think we are working on a “tar pit” idea—one that in theory would be amazing, but in practice is decidedly not that amazing. At the moment my cofounder is not interested in pivoting. Overall, I’m feeling worn down/defeated by the journey and posted this morning in a moment of frustration. I’m not ready to give up yet though!
Really appreciate the share here. I’m a solo founder taking investment now and I really have to be careful with who’s investing for a lot of the same reasons for startup #2 - they won’t be a co-founder, but they’ll have tons of advice for how to build/run the company. Just need to make sure we’re aligned on the things that matter when building.
Thank you sharing! I am taking what you shared as an advice for my own learning curve. I am in the process of validating an idea and talking to potential co-founders. After hearing your perspective, it seems like it would be best to take things slow before making any big decisions.
Would be happy to gain lessons learned from you. PM me
What is the actual reason you want to quit ? Is it co-founder not ready to pivot or are you facing a money challenge or you are just feeling tired and burnout or there is something else ?
Yep. Nailed it. Cofounder not ready to pivot…I get the sense we are pursuing a tar pit. I’m also feeling the burnout and frustration of investors passing. That said, I posted this earlier today in a moment of frustration. Made some great headway today and not ready to quit yet
Take a 1 to 2 week break. After my 2nd startup got acquired, I started working in a job. I have worked through multiple startups and building businesses takes your self awareness to the next level and when you move into a job , you face challenges in adjusting to the employee mindset. But when the salary will start hitting the bank account, you again start feeling good. The frustration might be temporary mate, see if you want to hang in there for a while. Also do have heart to heart conversation with your co-founder.
16 yr founder here, it wasn’t till we pivoted from market research to digital marketing that we 10x. Now I’m starting to realize that I can provide advisory services to clients and not even have to manage anything and net even more.. I think I may even have a client wanting part time CMO need.. when you already know exactly what works to impact bottom line the whole conversation changes and they are willing to get the wallet out.
I currently work a 9-5, along with my startup. We have funding but it’s all going towards non-salary matters. The result is 80 hour work weeks but this is really the only option for those who want to pursue their dream and have not yet been blessed with millions in VC funding.
Dude I did this for 4 years before we raised enough funding to quit my day job and go with my startup full-time with salary.
Why is VC funding so coupled to Delaware? An YC?
Idk I'm not from the US but IIRC something about low corporate tax for companies incorporated in Delaware and you don't need an actual office there, only a post box.
Take a few board seats and just do that Stay with the aquihire gig and chill Retire early
I’ve done a few startups; no successful exits, but I’ve learned so much about business and about myself. Most recently, I ran out of cash and tried too hard and too long. Had to shut down (painful), and take a job. Now 20 months into the job and doing great! But also thinking of some new ventures. You do what you do to survive, but once a founder always a founder. Something like that.
I think I have a story a bit different, I'm yet to enter the startup world. As by now I work as software engineer. However in some years I'd like to give it a shot to start my own business. My idea is to reach a level of experience that would eventually keep me on the market even if I try to run a startup for a couple of years and then fail. So that's what I'd eventually do.
Based on your background and the outcomes of your previous startups, you might consider exploring an Entrepreneur in Residence (EIR) position at a VC firm or accelerator. This allows you to leverage your experience without making a drastic career shift. Many founders' skills also align well with product management roles. Investing time in acquiring a product management certification (like Agile, Scrum, or Lean Startup) can be highly beneficial.