Panelists at last night’s discussion on managing family life and startups.

“Oh excuse me, it’s Amy,” said Brad Feld as he answered his wife’s phone call, while sitting on stage doing a live panel to a packed out room at the Hard Rock Cafe in Seattle. Priorities!

Many topics were covered during last night’s session, to share insights on how we, as entrepreneurs and workaholics, can “maintain fulfilling, loving relationships while working in the high demand world of startups.” At least that was the intent of the panel, and it certainly had heads in the crowd nodding along and voices practically uttering “amen.”

I know I was.

There were golden moments and tweetable take-aways, one of my favorite from Brad, saying: “If you spend all of your time talking about how to talk about your relationship, it will fail.” So meta, and so true. “Be present,” surely a mantra we could all do better by.

Setting priorities was a hot topic with Brad, Emily Huh (Cheezburger Network), Geraldine DeRuiter (Everywhereist), Rand Fishkin (SEOmoz), and Keith Smith (BigDoor). Brad certainly practiced what he preached when answering that timely call, and the crowd adored him for it.

Keith made it clear, in his usual sharp and witty deliveries, that his children reign supreme in his hectic life as a leader. His added comedy helped balance out moments where Emily shared her’s and her husband Ben’s earliest relationship memories, and Ben’s thoughts of suicide from being absolutely overwhelmed with debt and failure of a previous venture, or when Rand spoke of Geraldine’s pilocytic astrocytoma, or her tumor rather, and the seemingly insignificant, but very real arguments of if Rand “should or should not Google it” to find out more.

Shit got real.

Brad Feld

Pardon my language, but it’s true. These five sat up in front of a full room of friends and strangers, and shared real moments. Moments of weakness. Moments that could be shameful and lessening of their character.

But you know what? Knocking them down a peg was the last thing that appeared to be on the audience’s mind. Instead, the room showed empathy and embraced the vulnerability. It was a safe place to share because everyone there felt pieces of them sitting on stage talking right back at them.

Everyone was hungry to learn what tools and processes these community figureheads have acquired from their failures, mistakes, and battle scars, because they need help in their own lives. The lives that are generally kept hidden behind closed doors and are afraid to surface when in public.

It makes me think.

How many times have you been networking and was asked: “How’s it going with you or your startup?” All you can muster is the highlight reel of successes and momentum builders? How many of your social status updates only work to craft an image of how awesome you or your company is?

Sure, it makes sense. We want to be trusted as someone who is stable, can deliver, can succeed, is the right person to lock in that business deal with or to provide that round of financing. What we don’t want is to be the butt of a joke, or a gossip topic, or thought of as inadequate and unworthy. We’ve all worked extremely long and hard to position ourselves to create a life, business and future, and want to maintain that.

However, we have all been inundated and overwhelmed, kept up late at night worried about crunching those dwindling numbers in the bank account, flustered and frustrated that communication has broken down with a co-founder. We have all hit some severe roadblocks that truly shows what kind of person you are in how you can recover from it. Hiding it or avoiding it doesn’t make the issues less real or you any better.

Why then do we put so much energy into wearing a plastic face, staring at another plastic face who could be experiencing, or who has experienced, the same exact issue? I’m guilty of this myself, but it’s time to stop. It’s killing us.

Change is happening already.

Andy Sack understands the need for transparency very well. At TechStars, he has every founder stand in a circle, every single week, to share and drink to the highs as well as confronting and consoling the lows. Each year, it’s that circle that creates the strength of family because of its ability to be a safe place in being a real human being, flaws and all, and finding support.

There’s also a great YouTube series called DinnerDialogues, where Ben Huh (Cheezburger Network), Andy Liu (BuddyTV), Dan Shapiro (Sparkbuy), T.A. McCann (Gist), and Oren Etzioni (UW), sit down to share intimate and ugly details of their entrepreneurial journeys.

Brad’s book, Startup Life, and last night’s panel, is a great step towards creating a healthy dialogue about issues that need to be addressed, starting with the core; relationships. Buy the book, if not to read and apply it, then to support the courage of vulnerability and communication.

Before you know it, we may get real on depression, anxiety, and all of the other harsh symptoms that come with the tumultuous, yet oh so rewarding life, of being an entrepreneur. When you get real, you might just find the perspective or support that you need to overcome it, or provide it for somebody else. What a gift!

If you run into me at a future event and only get the highlight reel, please call me out and dig deeper. I’ll appreciate it and return the favor.

Kyle Kesterson is a GeekWire contributor. He is a serial entrepreneur and most recently co-founded Freak’n Genius. You can follow him on Twitter @kylekesterson.

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  • Joey Aquino

    Awesome post Kyle! Great recap and think the last ask is something that would make us all a better community. Write more! :)

  • Paul Watts

    Thank you for contributing this, Kyle. Having struggled with it most of my life, I find the current conversation around depression refreshing. It’s unfortunate that the impetus for this conversation were two highly publicized suicides, because in a better world it shouldn’t have come to this.

    We shouldn’t feel the need to hide our anxiety that if we’re not “crushing it,” it means we’re somehow not adequate. It’s impossible for everything in a startup to be 100% positive. But the pressure to put on that plastic face sometimes is too much to bear.

    While I still have stuggles with fears, anxiety and doubt, becoming an entrepreneur was one of the best things that I could have done to help battle my depression. It’s focused me on what doing what I love, and exercising my core strengths. It’s forced me to expand my horizons and conquer what I had previously feared. We can help other entrepreneurs overcome these difficulties in their lives, as long as we are all more open about it.

  • evanjacobs

    I think that most entrepreneurs really want to see everyone succeed and that part of the reason that we only share the highlights with each other is that we don’t want to discourage the other person (“Gosh, Kyle is such a superstar and if he’s struggling then what hope do I have?”)

    • Paul Watts

      Personally I don’t share this view, Evan. If I heard from someone like Kyle give voice to his struggles, those could be things I could identify with and then have hope there were others like me. In particular, if someone who is successful has had issues and have overcome them, that could give me hope that it is possible to come through what might sound insurmountable in the moment.

      To anyone who has struggled with depression and doubt, sometimes the best thing you can give them is the knowledge that they are not alone and it will get better.

    • Kyle Kesterson

      That’s a great point, and being able to maintain that encouragement while sharing a sense of realism may take some effort, as all meaningful things do. However I would rather share my optimism while instilling proper expectations, than setting a budding entrepreneur up for failure, making them think they are doing something wrong and feeling alone in their struggle.

      If we strengthen our communication muscles, we can address both our highs and lows, and speak intelligently and compassionately to them in a single conversation.

    • Kyle Kesterson

      Also, it was great seeing you last night and talking through some of the woes of fundraising. :)

  • facebook-37521058

    Anyone who thinks that Brad’s wife isn’t instructed to call him during interviews or keynotes is a complete moron, it’s all a marketing ploy as seen in this article. I’ve seen him do this in almost every keynote or interview he’s done. Do you really think his wife is calling him that much? Do you think his wife doesn’t have access to his Google calendar? Do you think his wife doesn’t know he’s keynoting at a conference? Do you think his wife really wants to interrupt all of these things to tell him to pick up eggs on the way home?

    Anyways, love the book, love Brad and the work he’s done in the startup space. Just thought it was interesting that he makes such a point about answering the phone in the most public of venues, and he also has a book about startup founders and relationship…

    I would have loved to see all the other speakers get calls from their significant others and interrupt the panel as well, how many calls do you think before the audience would have started to get mad?

    • Kyle Kesterson

      Your point of the validity of the timed call is moot. Whether or not it was theatrics, the call served to be a symbol that drove the point home.

      • facebook-37521058

        Yea, completely agree. I guess I just value authenticity more than anything else.

    • Bob Crimmins

      I don’t know Brad well enough to judge his motives for taking so many calls from Amy. But my first thought is NOT theatrical marketing. If anything, I would have guessed that it’s a routine to keep him honest. If I were Brad I could totally see myself telling my wife to call me every time I present to remind me of what’s important… all the time. It’s analogous to tying a string around your finger to remember to feed the dog. Even if it’s just a quick “hi, honey, I’m on stage right now so if this isn’t urgent I’ll call you back as soon as I’m off stage.” If it is urgent, then I’ve done the right thing by answering. If it’s not urgent, then it’s ten seconds well spent remembering that I’m not alone in this.

      Of course, if I’m wrong about Brad and it’s all just a smarmy marketing tactic then I reckon I’m a really bad judge of character.

  • Naysawn Naderi

    Nice post Kyle!

    I think part of the issue comes from people just asking “How’s the startup going?” and expecting a 15 second response. To anyone who’s ever been in the driver seat, it’s almost impossible to answer that question with in 15 seconds with anything that conveys the ups and downs while still sounding upbeat. So what tends to come out is “The Startup Is Going Great!”

    Maybe we should start asking fellow entrepreneurs, what have you learned recently about your startup rather than how it is going… We should probably be measuring success along the learning lines anyway in the early days.

    • Bob Crimmins

      Great comment, Naysawn. I’ve been thinking a lot about this the last few years as I’ve been exposed to more and more entrepreneurs (TechStars, TyE, Poker 2.0, GeeksOnATrail.) The result is… I’m on a mission. For the past year I have stopped asking “how’s it going with” Instead, when I run into a fellow founder I try to start by first asking “How is business?” The key here is that I do NOT ask them “How’s your startup”? I know there’s lots of product/customer/market greatness to brag about with your startup but, frankly, I’m looking for a response that includes “I’m really struggling with X.” If that response doesn’t come out, the I follow up with “What are you struggling most with?” And finally close with “How can I help?” After a little more than a year of this I can say that my drive-by conversations with entrepreneurs have become much more valuable and rewarding for me and, I hope, for them as well.

      • Kyle Kesterson

        Yeah Bob, you have gotten really good at both extracting issues and delivering value in a single conversation. I always appreciate the depth to which our conversations go, and you’re one of the most generous people to flip it back and share your time and energy.

        We need more Bobs.

  • Marc Barros

    One of the challenges to date is who is going to talk about these deeper subjects?

    Great summary from last night.

    Most investors don’t know what it’s like to be an entrepreneur so they don’t understand the challenges and therefore can’t talk about it. Plus they don’t want to admit publicy what their companies are struggling with. Momentum is a big part of raising more money at higher valuations. Brad is rare in this case.

    The media love to cover highs (success) or failures (drama). There isn’t much depth talked about with what a company is really facing. Also because most writers haven’t built company so they can’t related to the story as it unfolds, instead are more interested in content about success or failure, nothing in between.

    Entrepreneurs are supposed to say everything is awesome. Anything else will send the wrong message in the market place to investors, customers, partners, employees, etc. Thankfully more and more entrepreneurs are writing about what it’s really like to run a company. It forces you to be incredibly vulnerable, something not everyone is comfortable with.

    It’s good people are starting to talk about what it’s really like to run companies. It’s a life choice that is an incredibly demanding journey.

  • RunTheNumbers

    I was part of a founding team for a startup several years ago that didn’t have an ideal outcome. It wasn’t a spectacular flameout, but a somewhat slow realization that we were not going to succeed. I was in my mid-30s and couldn’t recognize what the situation, both then and after, were doing to me.

    A year after we closed our operation and moved on, I found myself digging up money to pay for a therapist. My health insurance wasn’t great, and the insurer didn’t cover mental health services at the time. Nonetheless, I was concerned about going to see a therapist and having that show up on my health records, lest someone find out about that later. My thoughts were if that information would ever get out, my chances of future startup endeavors and funding with investors would crash and burn.

    It was a very tough time for me and everyone in my circle. If I hadn’t sought help, things would not have turned out very positive. I’m personally very happy to see this subject come front-and-center. It’s too bad it has taken the suicides of a few well-known entrepreneurs to finally get us talking about it.

    While support among entrepreneurs is well and good, we need better professional mental health support in our communities. State government made mental health coverage in Washington compulsory with health insurance plans a few years ago (this has been expanded into Obamacare, I believe.) It is a start, but so much more needs to be done.

    • Kyle Kesterson

      Thanks so much for sharing. I have witnessed a multitude of startups experience the slow death, which I believe creates cloudier issues that are harder to recognize and address. If you’re a frog in boiling water, you never really understand or embrace what’s happening until it’s too late, and you’re left having to work to gain deep perspective in retrospect in order to fully heal and create tools around to prevent in the future.

      I think a method to prevent the slow death is to establish that healthy dialogue with those in your life and in your community. Getting loads of perspective at a rapid pace helps an entrepreneur “fail fast”, to get back up and go at it again.

      Regarding therapy, my experience was completely the opposite. I was a part of a startup that was having founder issues, and it was decided that it was best to try founder therapy, primarily for the perception of working it out FOR our investors. Ironic, eh?

      • RunTheNumbers

        Yes, “fail fast” has more benefits beyond the business value of learning and recycling. I wish we had a better plan back then, but that’s part of the learning cycle I suppose.

        We actually went through founders therapy as well, although it was something I wasn’t on board with at the time. It was an odd arrangement as the counselor already knew one of our founders, so the conversations were awkward. It caused trust issues.

        But I get the motivation to work things out for your investors. For me, I had the most success with therapy when I was essentially selfish about it for myself. The only way I was going to be of value was if I got my mind right, and the only way I could do that was to focus on myself. Being in a startup, I didn’t realize how much I was focusing on everything else and not taking time for myself.

    • Todd Martini

      Great comment. A lot of people have focused on what role startup stress might have played in Jody Sherman’s suicide and how the startup community addresses success and failure. This is not strictly a startup community issue. This is an issue that affects our society as a whole. It’s how we as a society address the issue of mental illness. People who suffer from mental illness hide it from people because they feel ashamed, because they feel less worthy or less capable because of it. Our focus should be on how to identify when someone is suffering from a severe mental illness (e.g. clinical depression; bipolar disorder) that could lead them to take their own life and then help them find a way to survive it. As you said better professional mental health support in communities is desperately needed. I would add that people need to be more observant as to what’s going on with the people around them.

  • Bob Crimmins

    Great post, Kyle. I regret that I wasn’t able to be there, as this is a topic of great interest to me. The good news is that I was with my kids. ;)

    I’ve learned a lot after 13 years and several startup “near misses”, including “the one that got away.” Chief among the many lessons is the general lesson that this shit is hard to do and all the smarts and hard work in the world does not guarantee success. The corollary to that lesson is that it’s not just hard for us, the entrepreneur, it’s also hard for our families.

    I’m sure there are exceptions, but in just about every case where I have gone deep with an entrepreneur on personal issues they are facing, their ambition, their passion and the risk they were willing to take to create a great business was not shared by their spouse. I’m so grateful that I’ve had so much support from my wife over all of these years but I also understand what I’ve asked of her is unreasonable by every possible measure. I try every day not to lose sight of that. I fail at that sometimes too.

    Dark days are a fact of life for startups and I’ve had my full share. If yours ever feel too dark then ring me up and let’s take a walk.

    • johnhcook

      Well said, Bob. Well said. And I too wanted to go, but I had the same (good) excuse that night. Running a startup with a family is certainly one of the hardest things about this job.

  • joewallin

    Great article!

  • Anon

    I missed the event, but it’s great to see entrepreneurs being vulnerable. It’s not easy to talk about their fears and concerns. I see too many entrepreneurs trying to feed their ego, project their own mythology and claim that they’re “crushing it” when statistically speaking, there’s no way that 95% of entrepreneurs are crushing it.

    Startups are hard and having people to empathize with is more valuable than just pretending they’re super successful.

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