An Extended Vacation

Starting tomorrow and for the next six weeks, the Gotham Gal and I will be on an extended vacation.

Every year I take the last two weeks of the summer at the beach with my family to celebrate my birthday and take advantage of the last days of the summer. I will be doing that starting tomorrow.

Then in late August, we drop our youngest child, Josh, off at college. That moment will mark the end of a very important part of our lives, the active in-person parenting phase, and the start of another phase where it will be mostly the two of us living together without our children at home.

Neither of us wanted to just drop Josh off at college and go back to work like nothing changed. We want to acknowledge this new phase and kick it off with an event of some kind. So we are going to spend most of September traveling together, just the two of  us, in southern Europe. We will be back in late September, with a new living situation, and hopefully refreshed and energized for this new phase of our lives.

We will refrain from working on this extended vacation unless something very important comes up. I will turn on an out of office responder at some point in the next 24 hours and when you email me you will get a reply saying that I’m away until the end of September and, unless its urgent, please contact me then.

I do plan to have something new up here at AVC every day during this period. That may be reblogging the Gotham Gal who plans to blog our trip in Europe, it may be reblogging some old posts that should get the light shined on them again (like I did earlier this week), it may be more videos (like saturdays), or it may be new posts if I am inspired to write something new and original. It will probably be a mix of all of that.

I’m super excited to be taking this time off. It was eleven years ago that Brad and I started USV and twenty four years ago that the Gotham Gal and I started our family. Both have been incredible and successful efforts, but they have required a lot of work. It’s time to take a break and smell the roses, together. And that is what we intend to do.

#life lessons

Comments (Archived):

  1. awaldstein

    Enjoy Fred.Southern Europe is magical. I won’t wax on about the wonders of what happens to wine in Northern Italy where it straddles the Slovinian border, or Etna where terroir literally comes from the sky.Or the amazing startup energy in unlikely places like Milan where in spite of generations of vacation in August culture, people are coding all night.Or sitting down to dinner in some out of the way place like Castelnuovo Berardenga where you can eat in someone’s home restaurant and everything from the meat to the wine is produced within a mile of the table.You know all of this.Have a great one.

    1. fredwilson

      Thanks Arnold. You are making me even more excited

      1. awaldstein

        I’m betting Portugal is somewhere in your travels. The ancient wines from Colares, grown in the sand on the beach are something obscure to savor.

      2. Carl Rahn Griffith

        Careful with Italy – it can, and most probably will, steal your heart – I warned Om about this; just look at his recent pictures/thoughts re: his Italian experiences ;-)Ciao! 🙂

    2. David Semeria

      Not *all* night Arnoldo ✌

  2. Fernando Gutierrez

    Congrats of closing that family phase successfully and enjoy your vacation. If you stop by Spain and want some tips, don’t hesitate in asking (@fernando in Twitter)

  3. Brian Crain

    Well deserved. Enjoy the vacations!

  4. LIAD

    my blessing to you is that at the end of your month one-on-one vacation you are as excited to spend a month one-on-one together as you were at the beginning.

    1. fredwilson


      1. Kasi Viswanathan Agilandam

        I was expecting a “Sure thing” or “thank you”…. !!!

  5. Abs Ghosh

    Great idea! Have fun!!

  6. William Mougayar

    That sounds like a wonderful rejuvenation plan. I hope you will eat lots of fresh fish from there, including many sardines! September is great in Europe because the masses finish their vacation in July/August, and the mad rush is over.

  7. leapy

    The great thing is that you recognised the opportunity to take this time together. What a glorious thing to do.

  8. Barry Nolan

    Where you end, I begin at the opposite end of the spectrum. My oldest small person starts her first day of school in September. I’m looking at 2032 before I can stroll around Southern Europe all through September. Hopefully by then the cellular roaming fees will be sorted.

    1. Jeff Judge

      Same here – first boy starts kindergarten with a boy and girl behind him. Good luck!Congratulations Fred. Such a great idea to take a month off to travel and return to a new living situation. Enjoy your vacation!

      1. Barry Nolan

        Ah the best of luck. My heart is breaking at the thought of her headed to school.

        1. pointsnfigures

          It’s so much fun!. Happy for your daughter.

        2. Donna Brewington White

          She will have so much to tell you!

          1. Barry Nolan

            Believe me, she’s totally cool with it. It’s the parents who are the blubbering mess!

        3. Jeff Judge

          I know. For me it has been acknowledgement of what so many parents with older kids keep telling my wife and I (“it goes by so fast”).

    2. JamesHRH

      Too funny – ism the midpoint. 12 & 9.

    3. Elia Freedman

      My youngest starts full day school this year, first grade. My oldest is in third. I have ten years to figure out how to afford a college education for them.

      1. Barry Nolan

        How is that going?I live in Ireland where asides from the abundance of VCs and absence of rain, one of the great benefits is a great state education system.Edit: Rain reference arseways.

        1. Elia Freedman

          I live in Portand, Oregon. We too have an abundance of rain and a shortage of VC. We moved to a school district specifically because of the quality of the public schools. So far we are really happy with the school the girls go to.

  9. Antonio Rocha-Ferreira

    Welcome to Portugal! See you there! 😉

  10. Ken Greenwood

    Congrats, cheers, and enjoy!

  11. JimHirshfield

    Congrats on the birthdays and anniversaries and on Josh’s exit (his liquidity event?).p.s. I write this from Stockholm with my family… taking a few weeks off, but can’t pull myself away from avc 😀

    1. Kasi Viswanathan Agilandam

      liquidity event …. ha…ha… I think your medulla-oblongata is filled with term sheets….

  12. Steve Poland

    Enjoy your time!

  13. Kasi Viswanathan Agilandam

    I am reminded of a ‘Tamil’ song which goes something like this …The orginal song starts like “50-lum aasai varum”….let me try translate (it is difficult to translate songs as they use uncommon words in tamil). “desire pours out even in 50’s as well … emotion join hands with desire and oozes …. there is no hidden secrets anymore … as it gets older …it is more enjoyable”….

  14. pointsnfigures

    Awesome. Empty nesting is fun. Our youngest turns 21 today, and goes back for her senior year on Tuesday. Eating my way around the Mediterranean is on my bucket list.

  15. Donna Brewington White

    “…smell the roses, together.”Fred, you are a poet!You do so many right things, right. This transition is one of them. I hope that this will be a time of wonderful surprises and special moments for you and GG.I anticipate some especially meaningful discoveries …and posts …to emerge from this time. No pressure. 🙂

  16. Tom Labus

    This is great. Wander, enjoy and have a great time.It will still be warm in September and Spain is calling you two

  17. Brad Dickason

    My wife and I just completed a month-long vacation (though I worked remotely for 2 weeks of it) and I can’t reccomend it enough. You will come back with a very different perspective as well as a list of what ‘not to do’ when you return :)If you haven’t finalized your itinerary yet, I highly recommend the south part of Sardinia (Cagliari and costa rei). We spent a month in this beautiful country where most of the citizens have never met an American. The beaches are beautiful, the mountains tall with lots of outdoorsy stuff… And the people are incredibly nice and friendly.My wife wrote a blog (http://30daysinsardegna.tum…) while we were there and if you’re interested, we can make reendations of places to stay/stuff to do. We booked the whole trip on airbnb and it was amazing.

    1. awaldstein

      very cool.

  18. AlexHammer

    You’re a good man and it is nice to see you enjoying the fruits of your great labors.Well deserved. Enjoy!

  19. Robert Holtz

    Bon Voyage, Fred and Gotham Gal. You more than earned this time off. Thank you for everything. Enjoy!

  20. meredithcollinz

    Wow! How beautiful! Have a wonderful time!

  21. Salt Shaker

    No one does Europe quite like the Griswold’s:Flight Attendant: Would you like something to drink?Ellen Griswold: No, thank you. Clark Griswold: I’ll have a Coke. Flight Attendant: Do you want that in the can? Clark Griswold: [Clark turns and looks at the bathroom] No, I’ll have it right here.Or an even better one …Ellen Griswold: Clark, you’re driving on the wrong side of the road! Clark Griswold: I realize that honey. I’m also on the wrong side of the car.Hope you blog a tad about your exploits. Quite envious to say the least….Safe travels!

    1. sigmaalgebra

      You are saying that the Wilson couple should take along Mark Twain’s ‘The Innocents Abroad’? :-)!

      1. Salt Shaker

        Ha…I’m sure they’re a bit more well seasoned than that, as does appear to be AVC’s readership. Would love to see AVC’s demo profile? Well educated w/ a standard bell curve on affluence? Interesting stat in yesterday’s WSJ. If I read it correctly, 15% of eligible employees never take the annual vacation they are due, likely often driven by a bunch of insecurities.Fred seems to have great balance–work, family, friends, philanthropy and a need for good old fashioned play, likely not ranked in that order of importance.

  22. JamesHRH

    Well played ;D

  23. Andrew Kennedy

    I hope you have a great one.

  24. Rodrigo

    Are you coming to Portugal? if so, feel free to ask for any help. Lisbon is beautiful and a worthwhile visit. You won’t regret it. Look here for some tips: (I’m not associated with that site but IMHO it’s the best one for tourists that come to Lisbon; even natives, like me, look at it). Enjoy the well deserved vacations.

  25. Anne Libby


  26. Twain Twain

    Lucky you and Gotham Girl! Southern Europe is a fantastic place to spend a month!If you haven’t done it yet, drive from Salerno towards Naples along the Amalfi Coast. The views are spectacular and some of the best seafood can be eaten in the family-run restaurants en route.If you’re going to Southern France and in Marseille, definitely catch the boat that goes towards Cannes.If you’re heading for Spain and are a foodie, go to Galicia. It’s also got Santiago de Compostela. If in Madrid, hire a car and drive out to El Escorial. It’s really something else as a royal palace.

  27. Mac

    Congratulations! I can relate. My wife and I have just finished our 24th year raising three sons. The youngest is now a senior in high school, so that gives us a year to plan the getaway. Looking forward to hearing about your adventures. I can see you being the Rick Steves of VCs.My wife (a.k.a. Miss Blue Marble) said no trip to Southern Europe is complete without spending time on Capri.Enjoy!

  28. jason wright

    Sounds exciting.Southern Europe. What line of latitude marks its beginning i wonder?

    1. Mac

      It may be just a state-of-mind

      1. jason wright

        the realm of the senses.

  29. Michael A M Davies

    At both ends of the spectrum; my middle daughter is off to college tomorrow, while my eleven month old is learning to walk, and they’re together for an extended vacation sailing in the BVIs

  30. leigh

    That’s awesome. I think marking moments are important and something we sometimes don’t allow ourselves the space to do so.

  31. Nick Crosthwaite

    A really great idea Fred! Enjoy the travels, change of pace and most of all the company

  32. Dayna Gant

    Fred, Enjoy, relax, sleep, dream! It’s been a wonderful 11 years watching USV develop into a powerhouse. What a cool way to start a new chapter.

  33. iggyfanlo

    Fred,I only really know you through this blog. I both envy and applaud your journey. We’re the same age (turning 53) and i wish you and the Gotham Gal the trip and experience of a lifetime.. both in Europe and upon your re-entry to the empty nest.Ciao

  34. harris497

    As someone who is on the journey that you are almost ending, (my second daughter is heading to college in two weeks) I wish you well. Kids don’t come with instruction manuals, so to be able to raise a brood to the point where they are college worthy:) is an achievement. Best to you and GG.

  35. andyswan

    I’m having a very difficult time coming up with a contrarian comment to this post.

    1. LE

      Not sure my comment would be contrarian, but I mentioned that I found the idea of going away for 6 weeks and putting on an auto responder stressful.The reason I feel that way is that if you have spent so much time using email for business purposes, and having good results by keeping in the loop, then the idea of not being connected is hard to handle and doesn’t feel “normal” to me.I think you have to go with the assumption that Fred really likes what he does and that is at least part of the reason he works as hard as he does. He gets good results and positive feedback. That’s not the same as traveling and perhaps relaxing. Definitely.I can tell you one thing though. When I was younger I sold my first business. And while I didn’t make a ton of money I made enough that I didn’t have to work right away and I could take my time and find something else to do. So I bought a boat and went out on it a few times and quickly discovered that I had way to much time on my hands and, most importantly, without the stress of work the boat really wasn’t any fun at all. It wasn’t like “wow this is great” it was like “wow I don’t really like this”. I’m glad I found that out when I was younger (probably around your age). That way I don’t have to think “wouldn’t it be great to not have to work” because I now know that’s not the case. At least if you enjoy what you do. If you are working some crappy job obviously things are quite different.

    2. jason wright

      you’ve got six weeks to come up with one.

    3. fredwilson

      Victory. I may have to retire. It wont get better than this 😉

      1. Dave Pinsen

        That would have been the contrarian comment: stretch the 6 weeks out to the rest of your lives. Declare victory. Retire.

      2. Ovidiu Schiopu

        I like to say: “It doesn’t get any better, only different.” We need to learn and constantly remind ourselves to live in and enjoy the moment. Constantly searching for that ONE instance of perfection is fruitless…

  36. Carl Rahn Griffith


  37. LaVonne Reimer

    Congrats! My daughters have been out of college a while (oldest just graduated from law school in spring). After being west-coasters all their lives they both decided in spring that NYC is the place they want to launch their respective careers. They head east in September. Does really feel like a new directions time for me too.

    1. LE

      There should be a service that hooks up people moving into NYC with roommates. My daughter moved after graduating this year and was lucky that she had a friend doing the same thing at the same time. However that friend won’t be permanent (she has a boyfriend) so my daughter will need a new roommate for sure. There should be some safe way to put together these types of living arrangements.

      1. LaVonne Reimer

        Funny. We’ve been going through the same thing. Probably something a bit more dedicated than comment threads at AVC! My youngest may or may not have a room to rent. Here’s my e-mail if a contact is of interest/needed. [email protected]

  38. Richard

    It takes practice to get good at most things. Spending a month away from your love affair with tech is no different. Be patient and, as with most ventures and adventures, good luck.

  39. BillMcNeely

    congrats Fred. You sound like you have done a great job preparing your children for success

  40. Jim Peterson

    Congrats on the new phase Fred and for taking the time to celebrate it!

  41. William Mougayar

    Instead of OOF, Daimler in Germany is testing a new scheme “Mail on Holiday”, where they automatically delete all your emails during your vacation, so you return to no new emails.…Apparently German workers already work 400 hours less than American, but they value time-off much more. Some companies and government already have rules in place preventing managers from contacting employers after work.

  42. RDC

    Need food tips for Puglia, Rome or Tuscany?

  43. Elia Freedman

    Congratulations, Fred. I hope it is a wonderful trip.

  44. Laura Yecies

    After 10,450 days of parenting our four kids we take our youngest to college today as well.Congratulations! I’m hoping it feels more like the first picture.

  45. CJ

    Congratulations Fred! Savor it all and enjoy it!

  46. Rohan

    Sounds wonderful and well deserved. Happy long vacation Joanne and Fred!

  47. Semil Shah

    Enjoy, Fred…in reading this, it seems like maybe you and your wife have been waiting years to take a trip like this. Will be fun to see if and how your writing changes as the year winds down.

  48. Francisco Prat

    Enjoy the time off. You guys will have a blast, make it to the north of Spain if you can. Pure bliss.

  49. RichardF

    Bon Vac – I’m off to Portugal with the family this weekend for a couple of weeks so if you could do another Fun Friday book suggestions post I’d be most grateful, need to fill up the kindle 😉

  50. sigmaalgebra

    Big congrats!

  51. LE

    To me, this actually sounds stressful and a major change.I know you travel a great deal, but I don’t remember a time period, at least since I have been reading, that you would have used an auto responder for six weeks.I’m not sure I personally envy what you are doing (although it seems the consensus here is others do) but obviously really hope you enjoy yourself. And most importantly when you return write a few posts about what it was like to come up for air like that.

  52. JLM

    .You will want to visit Florence where there are many statues commemorating the earliest VC negotiations. Here is one from one of the first down rounds done by the Medicis. The negotiations got a bit tense apparently.Bon voyage!JLM.

    1. scottythebody

      “No, I *WILL* have the right to participate pro-rata in future rounds !!!!

      1. JLM

        .There is apparently considerable evidence to suggest this was a conversation about prorata participation or a liquidation preference.Can you pick out the VC?JLM.

  53. JLM

    .The empty nest only gets better and better. Now to get rid of the dog?I skied six weeks this year and am headed to the beach for four weeks on Saturday.You can work from anywhere and probably do it better than you ever have before. Takes about a year to get it right.Those little beasties who used to live in your house before? Now they’re called visitors and they can come and go at their leisure as long as they always remember to ultimately go. They actually begin to think you get smarter and smarter.Who knew?JLM.

    1. LE

      You can work from anywhere and probably do it better than you ever have before.Except that Fred isn’t working. At all.We will refrain from working on this extended vacation unless something very important comes up. I will turn on an out of office responder at some point in the next 24 hoursI agree with you though that the best thing is to be able to work from anywhere and intermix working the way you are describing it if you can.That said, and this is important, no way you’d be (JLM) doing what you are able to do now if you hadn’t had your nose to the grindstone when you were younger. And ditto for Fred.This whole “see I didn’t have to work that hard” deathbed thing is bs. Only spoken by people who did work hard.

      1. JLM

        .Not to pick an argument with you but Fred is actually “working” when he relaxes as he is recharging his brain. That is part of the work-relax-work cycle.We are silly when we fail to recognize that refreshment is part of working no differently than working out at the gym and then recuperating is part of the body strengthening process.As to the deathbed utterance issue, of course you are right but the subtlety is that we allow our work to expand to fill the available time and we also compress the work to fill the same time.Many Type A folks trick themselves into thinking they are the only ones who can do the work at the requisite level of quality — that is a huge myth.Many times it is a distinction that only we ourselves can see and the world otherwise does not.I once was sick for 18 months and my contingency plan worked like a champ. The second I went down, the plan kicked into action and the company ran as good if not better. The one sure thing was the folks who stepped up — they really stepped up and made the entire team work better.As Charles Degaulle said: “The cemeteries are filled with indispensable men.”JLM.

        1. LE

          I once was sick for 18 months and my contingency plan worked like a champ. The second I went down, the plan kicked into action and the company ran as good if not better. The one sure thing was the folks who stepped up Ok, so let me share this one with you then.When I was in college my dad’s partner in his business was his brother. And his brother’s son (who was 5 years older than I was) worked in that business after graduating college. So he was in his 20’s let’s say.Out of nowhere (you know as opposed to “planned”) my dad had a heart attack. (This was the 70’s). But low and behold, my dad being the nice guy that he was (sometimes) and more importantly liking to teach in particular, had taught his nephew everything he knew. He never viewed him as a threat (primarily I’m guessing because of age). I mean my dad would teach him how to take care of the gift shows, and everything that went on in the office, and even how to handle the real estate. He would send him out for tenant problems and to meet with repair people and everything. He taught him everything and anything he could. My cousin liked that and my dad liked doing it. Positive reinforcement.My uncle, the going joke was, “didn’t know how to write a check”. He took care of the shipping and also traveled to buy merchandise. An important part of the business for sure. But he definitely needed my dad who was the business brains (and took real estate courses at night as an immigrant) and was good with math. My uncle wasn’t any of that.Well, after my Dad had the heart attack my nephew was able to easily run the business and do my Dad’s job.And my uncle saw that.So the next thing you know a year or two after my dad returned from his hospital stay my uncle angled to split the business in two because he realized he didn’t need my dad he could just have my cousin do what his brother did.And that’s exactly what happened. And the partnership ended.And you know, at my uncle’s funeral, his grandchildren got up and made a speech about their grandad (my uncle) and you know they didn’t even know that he had a partner when he started the business. It was as if my dad never existed at all (even though they obviously knew him).

          1. JLM

            .Great learning story.JLM.

          2. LE

            You know there is also the one, which is similar, as to why the bookkeeper who is embezzling never wants to take a vacation for fear of being exposed.Or the long time financial employee, where nobody has to counter sign checks, or even if they do it’s just a rubber stamp [1] that ends up pilfering the company.[1] Because “hey if anything we trust ‘Dave'”.

        2. LE

          Not to pick an argument with you but Fred is actually “working” when he relaxes as he is recharging his brain. That is part of the work-relax-work cycle.Well I think of sleep as very important in the same way.But I don’t think of “sleep” as work I think of “sleep” as maintenance. So I’m not sure I would categorize “relaxing” as work which is not the same as saying “relaxing” is not important. I mean to some people it is very important.

        3. LE

          By the way on the “deathbed” subject I just saw this story (regarding Howard Stern and an early interview with Robin Williams):…To wit:I was a bit of an a**hole in a lot of ways with guests. “I wasn’t rude with Robin Williams, but I asked some questions that perhaps went into areas that he had enough of… I think my whole demeanour and attitude was just s**tty. I wasn’t trying to be mean to Robin Williams. I was just trying to be provocative and interesting for the audience, and doing what it is that I thought had to be done. So there you have it. Howard Stern thinking that he would still be Howard Stern if he hadn’t been an asshole. Maybe he would have but my hunch is that’s what gave him an audience (like Rush Limbaugh or any other “character”).

    2. Tom Labus

      about that smarter part, anytime now. We’re on the edge of it

      1. JLM

        .There is nothing more gratifying than when your 28-year old Master of the Universe investment banker son says: “Damn, Dad, you really know a lot about business. Where did you learn all that stuff?”Of course, he has always thought of me as a professional basketball coach but that’s another story.If only we could be the men our Labradors think we are, no?JLM.

  54. Kirsten Lambertsen

    That’s sounds sublime 🙂 Glad GG has decided to take us all along with you!

  55. Mike Geer (MG)

    Safe and fun travels, Fred!

  56. mfeinstein

    Have a great break, Fred and Joanne!

  57. Emil Sotirov

    Sounds great! We may meet somewhere in Northern Greece – Halkidiki –… – if you’re going there… late September.

  58. scottythebody

    Very cool! In 24 hours I, too, will turn on the auto-responder and try my best to dis-engage for two weeks. I love to work hard then totally unplug. It feels completely insane for a day or two, but then it feels so right.

    1. scottythebody

      Napoli and Positano, as well as the national parks. I’m so stoked.

      1. JLM

        .Did someone say Positano?I love Positano. On top of that cliff is the Trail of the Gods which I hiked on a 105F day. Almost killed me because I thought it was 85F.When I came down at a church from the 1500s, I had a Coke. The best freakin’ Coke in the history of mankind.JLM.

  59. bsoist

    Congratulations and Enjoy!

  60. Alex Wolf

    A real vacation. The new luxury. Enjoy!

  61. Prithviya Jain

    My generic wording: “Need AFFORDABLE social media services for your small business? Visit my website:

  62. TNOLL

    Enjoy the roses…getting ready to walk through a new door myself with the birth of first child…scared as hell, but looking forward to the journey.

  63. aminTorres

    Have fun Fred!

  64. ShanaC

    Methinks you need a new hobby for after you get back.

  65. Fred Stutzman

    Congrats Fred. Enjoy the break.

  66. howardlindzon


  67. bijan

    awesome and congratulations. have a wonderful trip. i have told lauren more than once to cancel our return flight 🙂

  68. Ovidiu Schiopu

    Enjoy your well deserved vacation…don’t forget to smell the roses!

  69. Dave Hyndman

    “We want to acknowledge this new phase…” I love that. It’s too easy to stumble through life and not see the beauty and significance of our many milestones. Enjoy!

  70. dovcohn

    Mazel Tov, Fred. Enjoy the break.

  71. Boris Wertz

    September is by far the best month to go to Southern Europe – enjoy your vacation!

  72. Vlad Ciurca

    Where are you travelling in Europe?

  73. jasoncalacanis

    congrats! i watched you two raise your family so deftly during my 20s and took notes. such worldly, dynamic children. you should be very proud of the job you did! congrats and see you on the other side!

    1. fredwilson

      thanks Jason

  74. Bud Wyckoff

    Genuine, sincere and i might add a very impactful synopsis. A great example of what an honest person can accomplish in any and all their relationships. As a Dad, im in great appreciation for your thoughts. See you in September. Bud Wyckoff, NYC

  75. Gregory Boutte

    Very inspirational read. Makes me want to do this myself when my 4th kid leaves the nest. Lots of work ahead of us still… If you’re going to France, lmk, I have plenty of tips. Enjoy the well deserved break!

    1. fredwilson

      thanks Gregory.

  76. Wazi

    Fred – if you are in boondocks in Spain – the Chocolate ice-cream is divine.

  77. Jenn

    Hooray for you two! Now with my balanced life in France, I realize that I worked way too much without taking time to smell the roses. Now its different & I love it. Enjoy!

  78. Mario

    Beautiful post. Quite poignant, actually.