The eternal question: how old is too old?
Jack Weinberg said in a speech in 1964, "Never trust anyone over 30". Sometimes it feels the same mantra is repeated in the startup world.
A common myth is that technology is only understood by the young, or that startups require that youthful energy.
I'm here to tell you that's not the case.
Now I don't want to denigrate anyone who is young. We were all once younger than we are now and will all be older as well. Younger people have a certain perspective that is valuable, and have the energy to solve problems by brute force that someone older may not have.
But as a 49-year-old entrepreneur working on my 4th startup, I believe age gives me wisdom I lacked in my youth—and I prefer to work with others who have developed that wisdom.
That isn't to say wisdom is guaranteed as one ages—many older people are none the wiser—but without experience it's difficult to have wisdom.
Right now I'm working on Day Optimizer, a time management web app which uses guided workflows to help solopreneurs create daily plans.
Because of my experience, I can see gaps in the market that I wouldn't have been able to see when I was younger and create concepts & frameworks that I didn't have the experience to create earlier.
It's still not easy, but I have a better understanding of what my challenges are, which give me more conviction in pursuing solutions. I have a more nuanced view of the world and can see the forces at play in the system in ways that were hard when I had a limited experience with different parts of that system.
Having been an entrepreneur for the past 24 years, I can't always see what will be successful, but I have a good idea of what my priorities should be to find out. This allows me to "work smarter, not harder".
Which leads me to talk about temperament.
I spent much of my late 20s and 30s as a workaholic trying to build startups. Since I didn't have the experience to know what to focus on, I scattered my focus across several different areas. As a result, my health suffered and I missed some key life experiences during that time.
I think I was in my late 30s when my doctor said I needed to lose weight else I needed to go on cholesterol-lowering medication. That was a wake-up call to focus on the other aspects of my life besides my startup.
In my experience, younger people are more willing to sacrifice their personal life and health in pursuit of a startup, while successful older professionals assign more value to these aspects, even if they don't always align their work with those values.
I'm not going to claim it's wrong to pour everything into a startup. It's a bet being made, and sometimes that bet pays off.
But where I am in my life right now, I'm more careful with how I place my bets, and want to work with others who are no longer betting their current life & health on a future payoff—who've gained the wisdom to place smarter bets.
Thus, while I'm not excluding anyone of any age, as I start the search for a marketing/biz-dev co-founder, I'm specifically targeting people mid- to late-career because of their experience and temperament.
A closing note: I am still young too.
Those of you reading this who are 10, 20, 40 years older than me may be laughing and thinking about how young I myself sound, reflecting on how much more wisdom and experience you yourself have gained.
I accept that. I also think that's why no one should exclude anyone based on their age, even if we have preferences on who we like to work with. When working with younger people, I gain joy out of the cross-mentorship that occurs as we teach each other our perspectives.
In the journey of life, we can only relate to where we've been. It's difficult to understand where we'll be in 10 or 20 years.
However, I do know this: I'll still be creating. I'm too interested in life and all that it has to offer not to be.
I'm planning to live to be 120. The way I look at it is this: I started working at age 18, so I'm only 31 years into my adult life. I have another 71 years to go, which is more than 2 more lifetimes (and I've done a ton already).
So at 49 I'm just getting started.
...
P.S.: If you think you might want to work with me to grow Day Optimizer, check out my Cofounder Opportunity page. While I think the opportunity is best suited to a mid-to-late-career professional, even if you're early in your career, feel free to reach out. I'm keeping an open mind, and even if it's not a good fit, I'm always open to meeting interesting people.
That mantra comes from a 24 years old, according to wikipedia.
I'm almost 35 and I'd tell that I'd do better when I was under 30. I had so many bullets to shot, yet no proper aim. Now I may aim better yet not many bullets left. This probably sounds silly for my elders :)
Hope you'll find a cofounder that you both will work happily.
If you have good enough aim, you only need one bullet. :-)
But seriously, I think there are ways to regain your capacity as you get older. You may never reach that same level of energy as in your 20s, but there is a lot you can do to get close, and with that better aim, have overall better performance.
I work a lot fewer hours than I did when I was young, but those hours are a lot more effective. But to keep them effective, I am also spending time in my day to keep my mind and body in shape.
(As I wrote that, I realized it may be that my overall hours haven't changed, but how I allocated those hours between staying healthy and working has).
I view the time I spend exercising, meditating and cooking meals as critical to my work—even my sleep. When I skip these things, my work suffers. But I didn't truly learn this lesson until my late 30s, and I have to relearn it from time to time.
So the answer toward getting more "bullets" may lie outside what is traditionally seen as "work time".
Regardless, best of luck in using whatever bullets you can muster to achieve the things you want.
p.s.: Jack Weinberg was 24 when he said that quote. I grew up hearing it, but had never known its source. Apparently, it was also taken out of context; he didn't intend the meaning everyone ascribed to it later.
Thanks for the wise words.
"I think there are ways to regain your capacity as you get older." Hope this will hit me sooner than I expect.
I think it's important to have a co-founder with a complementary skillset, and similar priorities / values.
Age and experience are not necessarily indicators of success.
At 38 I agree that with age can come insight and patience.
There are some advantages however, that can come from being younger. You tend to be less jaded and you also have not yet learned from your industry that something is "impossible" and you may move forward with hope that isn't necessarily warranted but can still pay off.
An example is that about 8 years ago I started making a low code platform for internal tools at universities at my day job (its called Graphene for what its worth) but at the time I was told by more senior developers that it would never work - currently all of our internal tools have been migrated to the platform and developers enjoy it.
First, congratulations on making it work and doing the "impossible".
While I would agree that it is often the case that as you get older, there is a tendency to become jaded and view things as impossible. However, I don't think that has to be the case.
Certainly it can be easy to dismiss technologies when they are younger and not as capable. But early technologies often improve more rapidly than we expect (though not always—I was super-excited about VRML back in 1992, but we're only now getting usable VR).
In my view, it depends not only on your age, but the mindset with which you approach ideas and innovation. Some people remain open as they age (or get more open), while others start getting fixed in their ways.
There's good reasons for both, but I do this as far as startups go, it's better to err on the open side.
Absolutely it doesn't have to be the case - and its not always an advantage. I certainly aim to remain open myself.
I actually agree with your premise, I was just offering a possible upside to youth that is often invisible.
Trevor:
Thank you for sharing and I am in the same place but a few years ahead of you at 57. I am working on my second real startup and seeking a potential co-founder with marketing experience. I will check out your page.
If you're also looking for a co-founder, also check out my Notion document How to Find the Right Co-Founder. It's where I'm documenting my process and research, and may be helpful to you. I'll be updating this as I go through the process over the next couple of weeks, so just bookmark it to get the updates.
I also did an interview with Dr. Matthew Jones from Cofounder Clarity today that I'll create a separate post for once I have the video edited and uploaded to YouTube. He had some useful advice as well.
Thanks for this post Trevor, it really resonates! I am also 49 and in a similar vein plowed a massive amount of effort into my own ventures and helping build other people's dreams. I'll definitely get in touch via your Co-Founder opportunity page.
Looking forward to the conversation!
I have a similar outlook on this stuff - when I was younger, I was outwardly mature but inwardly very immature. I had a temper and got too emotionally invested in things.
Now that I'm older and have had the experience (and have chosen the right life partner), I have a similar outlook to you where I have the right temperament and a broader view of how to tackle problems.
I also don't have the worry I had a lot as I started my career about failing. Now that I've got a solid financial basis after putting in the work for more than a decade, I can think more clearly about problems instead of say, out of necessity (and perhaps desperation at times).
My only regret now is that I notice that it's "harder" for me to learn things because my mind is so much less malleable. I'm not making an excuse; I just notice that my mind more easily defaults to "I already know a better way to do that!" so I don't have the same curiosity or willingness to accept new information that I used to have. I say this in the context of language learning - I'm learning a new language now, but my brain always wants to default to my primary language because it already knows how to communicate things better, whereas in the past when I was younger, I absorbed and accepted new language information so much more easily and quickly.
Good luck with your search!
As someone who is also learning a new language, I can sympathize. Though from what I've read, we're actually better as adults learning new languages than we are when we're younger. The problem is that we have less time to practice and outcome is a result of both time and effectiveness.
For me, I do have to make the effort to continually learn. But in a similar way to work, I'm also no longer learning through brute force, which allows me to learn more efficiently.
With regards to language learning, my own current focus is on listening skills. I'm studying toward my B2 level in German. I've reached a point where I'm okay enough at reading, writing and speaking; and listening one-on-one works well. But once people are speaking too fast, with an accent I don't know, or in a group, my comprehension falls dramatically.
So I'm doing specific exercises to improve my listening skills, namely doing intensive listening (where I listen to a video while reading the subtitles, making sure I'm hearing every word that is said) and doing transcribing (where I take a video that has exact transcription, listen to it without subtitles and make my own transcription, then compare).
To me, this is what the "deliberate practice" in Malcolm Gladwell's 10,000 hours is all about. Using the experience you have gained to direct your attention to the areas you most need to improve.
I also think of learning capacity as a muscle, not a fuel tank. The more you do it, the better you get at it. Studying metacognition and "learning how to learn" can also be helpful.
Good luck with your language learning and everything else!
I'm encountering the exact same issues as you with my language learning, and actually using the same tactics as well! I realized doing a listening-based learning system (I use Pimsleur) was actually working pretty well for helping me to retain more of the language and use it more effectively.
You are totally right about the differences in learning as children vs. adults. I will say, I left my full-time job to become an indie hacker, and part of that was to get back more of that time to devote to learning the language. I've set a goal to have conversational proficiency by a certain date this year, and I'm really looking forward to getting to that point. But, just gotta make the time to work that muscle like you said!
You've inspired me to make the extra effort to practice more - thanks for that!
I'm 40, and I agree, the more time passes the wiser and more patient I get. And only know I understand the value of focusing on one thing at the time, instead of doing 5 things at the same time. I wish I understood also how to be more patient with money, and how to invest. But this is life :)
Theoretically investing is easy; in practice it's hard because you have to manage your own psychology.
From an investment perspective, I'm a big fan of the Permanent Portfolio as an "all-weather" portfolio. Even if you don't follow it exactly, it teaches some interesting concepts around portfolio construction and how money rotates between different asset classes in different market cycles.
Opposite from investing, this 4-part series from Mark Douglas on how to think like a professional trader is useful to watch, because it focuses on your mindset and psychology. I find the concepts around uncertainty and placing bets can also be applied to entrepreneurship.
Well health is definitely important, especially when we're playing this game for the long term. Being 23 myself, can understand what you're implying.
I would suggest to rephrase as “because of my experience”. Obviously, age gives more opportunities to gain experience, but it’s just one aspect of many.
I am 37
You are absolutely correct. The two can be correlated, but are not the same. Updated the text to reflect your suggestion.
Well said.
I'm currently 26, and until recently, the thought of aging petrified me.
Given how much I've learnt from experiences in just the past 4 years, now I truly can't wait to be 30 or 40. The wealth of personal insights I'll have will be unprecedented.
I admire your grit to stay so persistent!
well written..totally agree
( nod from an older generation )
nicely put.
Great perspective.
One thing I've noticed is that experience helps you identify what deserves attention and what doesn't. That's becoming increasingly valuable in a world full of notifications, tools, and constant context switching.
As a CortexSage user, that's exactly why I find it useful—it helps me keep context across projects and conversations instead of constantly rebuilding it from scratch.
Wisdom isn't just knowing more. Sometimes it's knowing what to ignore.
This resonates.
One thing I've noticed is that experience doesn't just improve judgment—it reduces unnecessary context switching. You get better at knowing what to ignore and where to focus your attention.
That's actually why I started using CortexSage. It helps me keep context across projects and conversations so I can spend more energy on decisions that matter instead of constantly reorienting myself.
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Thanks for including that link in the comments. I do think that research is important in dispelling the traditional myths.
This specific post was requested as an expansion of a comment I made on a post asking if 40 years was too old.
The value I think it provides in addition to the research is a more personal viewpoint into the basic premise.
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