After Your First Big Success, What’s Next?

As exits have been flowing nicely again the past few years, many of the entrepreneurs I work with have experienced their first big exit. I refer to this moment as when you find that you have life changing money in your bank account, which I like to call “fuck you money.” You now can do whatever you want with the rest of your life.

I was on a walk with an entrepreneur recently who was wrestling with this when we ran into another entrepreneur I had backed who had an exit a while ago and had wrestled with the question of “what’s next.” We chatted briefly and then he hopped on his bike and continued his ride.

Later in the day, I got the following magnificent note in my inbox from my bike-riding successful friend.

I was thinking about the ‘what’s next’ conversation. I’m sure you’ve seen everything and are all over it, but in my more limited experience, for some people it’s harder than the what’s first conversation (i.e. should I start a company or not?).

I find, unfortunately, that a reasonable percentage of people chase their tail endlessly looking for the next big win, but they can never catch it because they have no idea what they are chasing. Their life spirals inward as they get more unsure of themselves, more frustrated, more unhappy.

I think this state of uncertainty and self doubt causes more depression, divorce and addiction for some people than starting and running a company. Especially if they’ve never felt failure before. Now they fail all the time and they can’t figure it out.

I think it’s mostly because they never find passion again, or they look for it in the wrong places. There are a million things they can do in the world, but the spend most of their time looking for the next great technology company that sells a better widget, but doesn’t necessarily change their life in any meaningful way.

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

To me, that’s the real grand victory.

Totally brilliant. And so simple.

I had my first exit when I sold my first company (Feld Technologies) at age 28. After the dust settled and I had sold all the stock I’d received, I’d made somewhere between $1m and $2m after tax. When Amy and I talked about “what’s next” when I was 29.5 (about the time I finished working for the company that bought mine) one of the options for consideration was to retire and move to Homer, Alaska. I was making plenty of money consulting and, while I was investing much of the money I made from the sale into new companies as an angel investor, the idea of living in Homer was attractive. We figured we could easily live for the rest of our life on consulting income and what we’d managed to save, even if none of the angel investments I was making turned into anything. When one of them was acquired a few months later and we had another $1m after tax, we realized that we could easily live on $40k / year of cash in Homer, which would last us about 25 years if we made no other income.

We were deeply in the “should we just call it quits and go live a different life conversation.” But at almost 30, I just didn’t feel done, and in many ways I felt that I was just at the beginning of a new journey (which turned out to be true.) So we packed up, moved from Boston to Boulder, and decided to build a life in Colorado, while I continued to invest. This was 1995 and the path from there has been powerful and dramatic. By 1999 I had to ponder “what’s next” again after a number of my angel investments returned more money to me than I ever thought I’d have, and then again in 2002 after getting massively crushed by the collapse of the Internet bubble and losing even more money on paper than I expected I’d make cumulatively in my lifetime.

I’ve been through the “what’s next” discussion with Amy several times, including in 2004 when I doubled down on Mobius Venture Capital (instead of packing it up and calling it quits), in 2006 when we decided to start Techstars and Foundry Group, and again in 2013 after spending six months being extremely depressed.

Each time, I’m adjusted how I spend my life in the way my friend talks about in his final paragraph:

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

If you’ve recently had some success, as you go into the weekend, take some time out to ponder how you are you thinking about this. And share if you have any insights!

  • Steve Bell

    I went through this whole “first exit syndrome/process” for over 10 years after selling my Wi-Fi to HP-Agilent in 2000. Happily, in the past year I’ve finally broken out of that phase. But boy, did I learn a lot – all clear in retrospective now.

    I spent two years working for the acquiring company (HP-Agilent; SVNL was the first acquisition to cross the tape when Agilent split from HP), traveling internationally, and expanding the business to include operations in Europe and Asia. Then I quit, moved to the Big Island of Hawaii, started a family at age 46 (my son and daughter are now 11 & 13).

    Starting in 1994, when I had first acquired some real capital through consulting, I had developed a passion for short-term trading (equities, options, futures, etc). So I got my Series 7 & 63 licenses, a Level-2, 20-screen trading setup, and went all-in for that (I’m mentioned in the forward of 3 books on short-term trading). But it turned out, I was just an “average” trader; I’d be up one year, and down the next. Although I enjoyed doing it, I eventually figured out that I did not have a natural “gift” for it, like the one I had developed for starting and building tech companies.

    I went for advanced Scuba diving certifications, worked out several hours a day, studied nutrition, discovered “GTD” (David Allen’s first book had just come out), and developed a software application (freeware written in Visual Basic for Excel) as an experiment. I read every book I had ever wanted to read; got extremely organized; and after 18 months developed a bad case of “Island Fever”.

    Retirement, you see, is HIGHLY OVER-RATED. At least for me, it is. I purchased an “ATA Air Pass” and started flying back and forth to Silicon Valley; at two years I was living in downtown San Francisco and dealing with the ramifications of having a lightly Autistic, but wonderful little daughter.

    So eventually I came back to doing what I’m truly good at – creating and building startups. But I got lost for quite a while there! Like 6 or 7 YEARS. There was a divorce related to handling the Autism; a lot of bad times, but also growth. I can definitely relate to what “bike-riding successful friend” said; it rings true.

    Right now I’m having more fun than ever, and the thing is – it ISN’T ABOUT THE MONEY. It’s about following my passion for the things I’m interested in. In addition to building a new startup, I’m into contributing to charities I care about; my kids; and being involved in state and national politics as a volunteer. Dealing with “the first exit” turned out to be almost more difficult, than CREATING it was:) So your post really struck home for me.

    If there are any entrepreneurs struggling with this, feel free to contact me. I’d be happy to have a private chat about it. I probably have more time than Brad to talk! 🙂

    I’m pretty sure I could write a book on this topic! There is a syndrome I’ve noticed where guys in their middle years, say 40’s roughly, get “stuck in a rut”. Whether they’ve had a first exit, or not. Well, I think I’ve become a “rut breakout” expert. Learn by doing, right?

    • Glad you’ve broken out of the rut and are having a blast!

      • Steve Bell

        It wasn’t so much a rut for me, Brad… it was about finding out what my true calling was. I actually don’t understand why the whole experience turned me into a “rut escape expert”… some things remain a mystery, right? 🙂 But i have helped a lot of guys get out of ruts since going thru it all. The bigger thing was, I got clarity about what I’m passionate about, and why.

        Thanks for your blog, I’ve enjoyed it for years now. And as you know, I am a big Brad Feld fan because (ok there are some other, business reasons) you were the classy person who reached out when my Mom died in 2011. She was a HUGE fan, you know! Mom, out in Wichita, Kansas not far from Boulder.

  • Jo T.

    Brad, this is (another) great post.

    When money falls from the skies, many people have this internal debate: “was I skillful–or, lucky?”

    IMO, one can never know the answer to that question. I’ve seen entrepreneurs and VCs who consider themselves skillful–and, some becoming pretty raging a-holes. I’ve seen others think that they were lucky, and then, start more initiatives to prove that they were in fact skillful. And, when things don’t go as well in terms of the financial metrics, they really bum out. Or, they feel like they’re frauds and a fear builds that they one day will be “found out.”

    I think people obviously are free to do what they want. But, I strongly feel that when fortunes and fortune arrive, it’s important to just *accept* them and not dwell on the root cause. Then, plan for the future and move forward.

    Hope all is well with you….

    • Nice – I think I know some of the same raging assholes as you do! I wish there was a word for “luck”+”skill” since success is almost always some blend of both.

  • I think the key to answering the “what’s next” question is to examine yourself closely. Most people tend to live one dimensional lives where their work and job title define them and this can lead to a meaningless life even after a great exit.

    I’ve always prided myself on having different interests and hobbies. For example, I went from being a fashion designer to an angel investor and now I am investing in not only ordinary tech startups but fashion tech startups. How convenient did that turn out to be? I know that even after my VC career is over, I can have many different endeavors to fall back on and I think once you have that in place, you will have things that will keep you busy for many lifetimes.

    All I know is, life is abundant in so many ways; we just have to open our minds enough to see it.

    • I love the “open our minds” phrase. It’s really fucking hard to open one’s mind, especially when you are either grinding it out or disoriented after a life changing event like an exit. But those are the most important times to open our minds.

      • Frank Traylor

        Wonderful post. As you suggest the question applies whether you are “grinding it out or disoriented after a life changing event like an exit” I recently had an exit that was more of a oh fuck than a fuck you. Still, it provided the opportunity for reflection on what’s important, what I like, how I can help.

        That reflection, the “open our minds” exercise is important at all stages of life and should be considered constantly. Our youth seem confused and anxious when trying to pick a path from those laid in front of them when the answers must be found inside. Later they may consider marriage, have an “oh fuck” exit, have a FU exit; each time reevaluating what’s important. Is this more difficult with a lot of money in the bank? I wouldn’t know.

        I’ve found new excitement mentoring entrepreneurs, helping companies navigate the marijuana market, studying genomic data analysis (related to MJ), and teaching kids skiing. Life is good and if I keep my mind open it should continue to get better.

  • Good post. Just wanted to leave a comment here to put in a good word for philanthropy. IMHO, it’s just as important to give money as well as time.

    • Totally agree. Amy and I are giving away all of our money while we are alive. I don’t know if you know about the Entrepreneurs Foundation of Colorado –, but Gnip just gave away over $587,000 as a gift resulting from their sale to Twitter. When you are a product of a community, giving back is incredibly satisfying.

  • Dave Girouard

    I have a theory that people are either achievement-oriented or relationship-oriented. Or if not binary, at least that they are dominant in one dimension or the other. Achievement types (which most entrepreneurs are, as well as most successful business people, athletes etc) can and do become addicted to achievement. A successful outcome in a startup is a high-water mark in this regard. But for these types, it will rarely be enough. Like any good drug, the effect wears off and you need another hit. If properly calibrated and tempered, achievement-oriented people can be among the world’s greats. But taken too far, they can become utterly disastrous to themselves and those around them.

    Relationship-motivated people derive much more innate happiness from their relationships with others and the communities that they’re part of. They tend to have much more co-dependent lifestyles, get great joy from the others in their lives, and suffer when the give/take of their various relationships if off kilter. They don’t derive nearly as much personal satisfaction from a personal achievement (eg PR in a race) but instead get satisfaction from the quality of an experience or even a conversation.

    I know this because I’m one of these, and my wife is the other.

    What does this have to do with “what’s next”? If the person-of-interest is indeed the “achievement motivated individual, and has exited from a startup successfully, they likely have already reached the addictive level. In many cases, it makes perfect sense for them to “try again” and hopefully enjoy the ride. But if enjoyment and fulfillment only comes from success, then there’s a lot of risk in this.

    Ultimately, I believe these individuals need to build strength on their relationship side – to lessen the dominant trait of being achievement oriented, and become more balanced people who can thrive based on the quality of their relationships. It also helps if their self esteem is “satisfied” – that they don’t feel the need to prove their worth to the world.

    Hope this wasn’t too far off topic – but it’s how I think about this exact issue.

    • Jana

      No it wasn’t off topic. It helped me. :- ) I haven’t had a successful startup yet to have a successful exit. But I have these exact feelings all the time. Same struggles. I think my need to prove my worth to the world is pretty darn strong, especially prove myself to all my past bullies. Maybe I’m sickly twisted, but somehow a successful startup would mean to me “Fuck You Bullies” I seem to want that pretty bad. But not as much as I want to help people on a mass scale.

      I guess I can look forward to having to deal with crazy lost feelings of what to do upon a successful exit. Maybe I’ll find all the bullies and do something good for them.

      • Bullies often get really confused when you give them a hug.

        • Jana

          Yep, it takes the power out of their punches. Disables their brains and maybe removes a bit of the evil that haunts them. I’d like to be free of what haunts me, yet it gives me motivation to help others. Maybe if I ever get to “Exit Stage Money” I’ll invest in all kinds of anti-bullying and PTSD organizations. I’ll develop the app that helps people who are haunted by abuse and PTSD, become free. It’s easy for humans to abuse others, but it’s not as easy to heal from that abuse.

          I really love this post Mr. Feld. I’m probably more off topic than the man who thought he was off topic. Yet for me to add to my startup journey a new fantasy of “What Will I Do When I Exit Successfully?” Well, I’ll be doing good and helping people heal I hope, and having a bit of long deserved FUN. Surly, I’d love to be the person who plants secret stash’s of cash around town, and leaves clues on the internet to find it. Love that person! That’s fun.

          For now, I have a lot of work to do! Thanks for sharing all these great comments. It’s been inspiring reading them and adds positive reason to be successful! Other than my sickly twisted secret of revenge!

          Catch up with you “Exit Rock Stars Later” ; – )

        • Gennady Shenker

          This comment made me smile, Brad. 🙂

    • Great thoughts. It’s like my rant on “introvert vs. extrovert” – the key to get started is to first “know thyself.” And then nurture this, while building strength in the part of you that is weak. I’m a deep introvert who is very comfortable in an extrovert world, but it’s taken a lot of work, practice, and understanding to get there. And – when I overdo the extrovert, I melt down really really hard.

      Achievement / Relationship is another spectrum. Amy and I talk about this in our Startup Life book. We recall the story of our friend who was going to be happy when he “just had $5m.” He sold his company and had $5m, then he needed $10m. He exceeded that and his number went up to $20m. He didn’t get off this particular achievement treadmill until he had a serious physical injury (life threatening – now fully recovered) in his early 40s. Suddenly he realized he had enough money – and focused on other things.

      • DJ

        Ugh. I know that feeling all to well. Lost a bundle thinking I just needed to hold out a little longer to get to the next level. Fortunately I did manage to take a little off the table before it was too late and still have my health.

  • Patrick Finnegan

    Brad what a great piece of writing. First off I want to say thank you for sharing this advice to young people like me who right now all we want to do is either make a huge impact or get a company acquired when in actuality its core is if you are making a change and helping people. I also agree that a lot of people including my father after retiring from Wall St didn’t know what to do and it wasn’t until he started giving back and helping organizations out, something he didn’t intend on doing originally that he found the answer to “What’s Next”. It is one thing to make money and keep it all to yourself but it is another thing when you do what you did in terms of helping communities, investing in companies, and giving people advice or letting them use you as a soundboard. I can’t wait to giveback after I solve a product niche and sell it, I definitely won’t be selfish and buy materialism because as the famous adage goes, Money doensn’t go with you when you die.

  • For the last three months, I’ve been rolling this question around in my head like a big, lopsided boulder. I quickly realized that building another company, or helping friends with their companies, is not where I want to spend my time now, even though that’s what I told myself I’d do once I hit FU money stage. Instead, I’ve been focusing on things that excite me AND aren’t at all attached to money. And a hell of a lot of mountain biking!

    The easy path (for me) would be to double-down, get back to work and keep on working. I’m finding it harder to give myself the space to feel a little lost, to wander, to talk to interesting people, and see where it takes me. I believe passions don’t develop overnight, but are kindled from embers of things that are intriguing to us and then occasionally burst into flame. Feeling grateful to be in such a lucky position is an important aspect of all this, and I hope everyone gets the chance to experience it. For all the “negatives” of figuring out what to do, life doesn’t get much better than financial freedom to do whatever the hell you please!

    • Jana

      Sounds Awesome to me! Especially the last sentence.

  • I loved that post, Brad.
    There is a feeling of liberation when you say to yourself “you can do whatever you want”, but one could argue that you need to follow your passion with or without money security.

    • Important statement – money is not the thing that enables this. Having money is a complex trigger – suddenly you can feel liberated, but many get confused and constrained as they try to generate “more” success, whatever that means. The money doesn’t really provide the security – just the illusion of security, especially when we remember that we all die and money can’t provide immortality at this point.

      • Preston

        I love how Brad states “at this point” when referring to immortality. We don’t know, what we don’t know yet and that’s the fun part. The next great thing in our lives is coming. We just have to be open to recognizing it.

  • Henry Glover

    Thank you Brad. My wife and I have had similar discussions. Profit and success has its rewards but at the same time fleeting. We have been considering starting a non-profit around teaching and education. It is encouraging to hear your thoughts.

    • Good stuff. Amy and I have helped create several non-profits – just holler directly if I can give you any help / advice.

      • Henry Glover

        Awesome thanks!

  • Eli

    Great post,
    Personally, I don’t want to achieve massive success.
    I currently build things, some of them make me enough money to survive, or a little bit more.
    I don’t have much self discipline, and massive success will make me into self centered ego focused person.. I love the fact that I don’t even take a bus now, because walking doesn’t cost money. I love to walk and see the world and to breath, and I know that it would not happen if I make it big, I would just take a taxi every day. I love to know that the people who approach me, and like me, are genuine, without any other motives.
    As funny as it is, my life quality is better when I am unsuccessful and a bit worried about money. I am more productive, less ego centered, and I experience the world and its challenges better. I also think I learn more.
    Surviving on the journey is the way to go for me, and I hope it won’t change, for better or worse.
    In the same time, I congratulate and happy for everyone who has made it, and actually became a better person after achieving success.

    • The journey is what matters, as you so nicely point out near the end. Success is not the driver of the actual journey but a lot of people forget that.

  • Lars Mapstead

    Thanks Brad, I think this is an issue for many who are self made, in the silly valley and beyond. For me, I keep chasing the next addictive nugget, fun win, but at the same time I realize, balance is key, and I have split my time into many areas of interest. I have still not quite figured it out, but with time I am learning to fit into these new FU Money Shoes 🙂 I have tired a lot of Different things, and for me the thing I ahve found to be the most uplifting, is building my relationships with others. Much as Dave Girouard has stated in these comments. So I try and Have lunch with many people every week, and see if i can be helpful , or just enjoying good converstion, It turns out you dont need any money at all to do that 🙂

    • For a lot of people, money is the liberator that let’s you realize all the amazing things you can do in life that don’t need money. Sounds like you’ve found some of them!

      • Lars Mapstead

        Well Growing up super Poor and Hitting the FU Money, I always thought that would fix it, but then you get a whole new set of hassles. I have to keep telling myself like the person above, This IS whats Next the right here and right now…… We are doing it every moment.


    “Totally brilliant. And so simple.”
    Brilliant maybe. Simple… No! As you know, Brad, I’ve been looking for something to get really excited about for years. After doing my EHR system. Which was 3 years of super intense design and implementation work. First I created a dsl, domain specific language, then created the system with it. Then another couple years trying not to give up because of no traction. Now I’m in a situation where I can’t find anything to get me really excited. I’ve even been looking at things that aren’t exciting.
    Mentoring… I do that. Getting out and enjoying nature… I do that. Dangerous things to get a “quick fix” adrenaline high… I do that. Find something that’s lucrative and exciting where other people can get excited too… I can’t seen to do that!
    If you want to be retired then yes “…so simple”. If you want to feel focused, driven, and passionate. Well again that’s not so simple. I’ll tell you what’s even more difficult than finding something new to get excited about. It’s finding people who get excited about anything!

    • Hint: Don’t rely on other people. Only focus on what gets YOU excited.


        Good point, thanks!
        I do really like seeing others get excited about things. I’d like to find a whole country full of go getters. Instead of boring drunks.

    • Lars Mapstead

      I have to totally agree, what other people think I should be doing does not cut it at all 🙂 I really like this thread its making me think.

  • The funny thing is I’m just starting adulthood and I’m always thinking ‘what’s next’ in order to achieve my dream (million dollar exit), relax and not have to think about what’s next. From reading this post and some of these comments, I guess you’re always thinking about what’s next even after you’ve ‘made it’. I mean what about just living in the moment that you desired for so long? I think the most important lesson I take away from this is to always follow my passion and my heart in whatever I do as it’s the journey that counts, and not the destination.

    • There is deep wisdom in living in the moment.

      • Lars Mapstead

        I believe it comes easier for some than others just like everything in life. But even knowing that you can work on this, can set you many steps ahead in the game 🙂

    • Lars Mapstead

      Living in the moment is the true key, but its very elusive 🙂

      • Indeed. The magic trick is to always be practicing!

  • Mtell

    I sold my startup, that me and a bunch of college friends started right out of school, 3 years ago for $150 m (we didn’t have VC so we got to split it amongst ourselfs. I enjoy a very average lifestyle so I have enough of FU money). After I worked of my time at the company that bought us I went right out and started a new company and raised a significant seed round, but I have realized that all the simple things that gave me kicks the first time around like your first employee, customer, even mundane stuff like having to deal with payroll doesn’t give me remotely the same satisfaction. But for some reason all the bad stuff like stress an anxiety over wether your product will fly is still equally hard on me making this time a much more negative experience so far. Any thoughts?


      You’re only a virgin once!
      The wanting is what’s most exciting.
      There are only two kinds of people in the world: Those that create and those that destroy.
      Lot’s of us are bored and wanting something new and exciting to get involved with.
      Most people are lazy and brainwashed.

  • For me such a ‘FU money’ event coincided with a break-up of a 16-year partnership that was entrepreneurial, rewarding, learning and ultimately lucrative. Though we kept the breakup publicly amicable and the surviving company didn’t lose customers or employees, the individuals separating went through a professional divorce nonetheless. My partner (the ‘dad’ of the business) and me (the ‘mom’) had our distinctive styles and mannerisms and at a certain point of the company’s existence only one could stay. I chose not to stay.

    You (Brad) have often recounted lessons from books, and one was recommended to me during this breakup – a 1960s publication called Seasons of a Man’s life. Written toward the phases men encounter from early childhood. it helped me see and understand the emotions I, in my 40s, was experiencing. The book was largely introspective and suggested to look at key events like this breakup as end of a life – something had to die before rebirth. This approach to reincarnation made total sense to me, a Hindu, but I had much to learn.

    I tried to take the lesson to heart and began the dying but never really completed it. I met the many startup people I now call close friends and began the journey that we would collectively name startupiowa. The work, though rewarding, kept nagging because (probably) I had never shed the old skin. The pull of the old life battled with the concurrent love for the current startup community. I helped launch and support many startup community projects and tried to remain true to the spirit outlined in the startup communities book. The works remained rewarding despite the normal ups and downs. It took me out of my comfort zones many times, thrusting into public speaking and the newspaper articles that caused more anxiety than anything else I’d felt before. I spent time and money traveling, acquiring new hobbies, etc., and finally beginning to read more. All positive experiences but none complete.

    For me, the turning point came when an email from my local YMCA encouraged me to join a workout class for diabetics (I am one). A close family member and fellow entrepreneur had just been diagnosed with Parkinsons and she encouraged me to join her team to run a 5k race (I’m not a runner and detest the idea), my wife gently encouraged me to join her in a bodypump class at the Y. Over the past year, I’ve been able to do all three. We ran the same 5K a second time this year (I still don’t like it but appreciate the time with Team Fox(y) for Parkinson’s Research). And, this weekend, I became certified to teach bodypump – a feat for someone like me who had never been in a fitness class just a year ago. So, the figurative death is coming almost 4 years later, but this time it seems to be real. And the catalysts have absolutely nothing to do with my past life.

    Though being able to walk away before has made it easier for me to euthanize projects that aren’t working, it remains hard to explain to others why certain things must be left behind. As I read comments to your post, it’s evident to me our struggles are individual, and thus our paths are uniquely ours to discover and pave. I’m curious to find out what the second part of life has in store for me

    • Powerful story Tej – thx for sharing.