13 startup founders share what keeps them awake at night

The greatest strength of the entrepreneurial mind is also one of its greatest weaknesses. The energy, creativity and passion that drives most founders can also lead to sleepless nights and distraction. These nagging ideas can be the next brilliant business idea or needless worries. We asked founders 3 questions to find out how they manage these thoughts.

“How startup founders deal with ideas and worries that keep them awake at night.” @WPCurve goo.gl/mMm9Ge – CLICK TO TWEET

  • What keeps you awake at night? An opportunity, problem, new idea?
  • How do you confront or manage these thoughts?
  • What’s the best way to turn these thoughts into something valuable?

Their responses were surprisingly diverse and creative.

Ideas

oatmeal

Source: The Oatmeal

New ideas can rob you of your sleep, fill your mind with possibilities. Usually these lead to a regrettable domain name registration. Sometimes it’s true inspiration for a big new idea. These founders have learned to capitalize on late night creativity.

Scott Paul, Founder – ArmorActive, Instafluence

Scott-Paul-web

New ideas keep me up, and usually not in the way you would think. I get to bed fine, but at 3am every few months, I get fixed on an idea that doesn’t allow me to go back to sleep. Sometimes it’s a hallucination and other times it’s genius. I have made a promise not to buy domain names while in these idea bombs until I have waited a few hours.

I use to just share all the ideas but now I keep an Evernote file and log them all. I have a system for keeping the ones that keep popping into my head resurface to the top of my notes. I have become very skeptical of my own ideas and do a little “Gollum and Smeagol” dialogue in my head and see who wins.

smeagol-gollum

So how do I create value with these ideas? I simply pass them around to everyone I meet in the day. I would say that is mostly what I do for a job right now. I am an idea broker. I see what sticks with certain people and I see if the idea passes some social tests and then I decide if it is worth pitching, building a team around, funding, or killing. Most get spun around in a few circles. We talk to perceived competitors or failed ventures in the space to see if there is any reason we would do better. If we pass all these tests then we throw about $1k at the whole thing to build some clunky version of the product we have in mind.

The value lies in testing an idea before taking it to investors and raising money. You can do so many experiments before that time comes, yet I myself have failed there and see so many others making that mistake. The cost of following any idea to the end will take years off your life, so find ways to really make sure you are not just doing something because it sounded like a good idea in the night. Go try to convince yourself in every way that it isn’t a good idea by asking everyone around you if the problem you want to solve even exists. If you can’t get others to convince you or convince yourself, run with it a little more.

Ben Hebert, Co-founder – Natural Stacks

Ben-web

Source: ticketbox.vn

I do my best work at night. It’s when I’m most creative.

There’s no more emails are coming in. I’ve already done my tasks for the day and I get to drink Jameson.

Working distraction free allows me to really explore ways to grow my business’s new opportunities. Opportunities could mean business ventures, collaborations, sponsorships, whatever.

Everything that you do is valuable. It doesn’t matter if writing a blog post once a week eventually turns you into a blogstar or something like that. It matters that you did it.

The only reason I’ve been able to find a modicum of success as an entrepreneur has been because I’ve always been doing things… creating.

By taking action on your thoughts or ideas, you’re getting experience and growing your network.

Chris Ducker, Founder – Virtual Staff Finder

Ducker-quote-web

Source: Foundrmag.com

If I do have problems falling asleep at night (which is rarely), it’s usually down to an upcoming launch, or speaking engagement. Is everything setup properly? Have I covered everything I’m supposed to, or want to cover? That type of stuff.

​I have a pad and paper next to my bed that I keep handy to write these thoughts down. I have done that for years. It’s the only way to get those thoughts and ideas out of your head properly!

If I end up making notes like this, I’ll review them​ in the morning. Normally, I’ll take a quick snapshot of the note and upload it directly to Dropbox. Sometimes I’ll share them with my team, sometimes I simply store them for later use. The most important thing is that they’re out of my head and away from my bed! That way there’s always a “clean slate” for additional thoughts and ideas.

Bryan Eisenberg & Marc Smookler Co-founders – IdealSpot

Bryan and Marc co-answered our questions, so there’s a little of both in this response.

New ideas never stop—it’s a curse. Whether its a new business idea, or different ways to slice a current project. It doesn’t end. And once an idea pops up, it’s hard to fall (back) asleep because you are already running through the traps in your head.

Regarding opportunities, for me, it’s more about opportunity cost. Are we as a company focusing on the right things, at the right time, at the right resource allocation? I am constantly running and changing scenarios in my head.

Regarding problems, in another business (life), I was the founder/highest escalation point for customer service for a business critical system (phone systems). Imagine selling over 10k phone systems across the world with VoIP as the backbone and the user has full control of the call menus—not a good combination. That lesson has made me ultra-sensitive to customer service. I find myself answering customer emails well into the night. And, more importantly, customer issues “usually” translate into deeper, more symptomatic issues with the product or service—which kicks off even more restlessness throughout the night.

As much as I try to compartmentalize it, the only trick that seems to work for me is to give my mind a vacation through activity like reading a good book, or playing a deeply intense video game where I can break the constant cycle. One other key factor in managing this is working with solid team players and great co-founders. If you look at our team at IdealSpot, we have a really outstanding and well balanced team. Andrew Hunter our CTO, also a multi-startup veteran, gets scale having worked on one of the initial Facebook gaming platforms. From a marketing and vision perspective, the Eisenberg brothers are just worldwide known rock stars.

In general, I find my tendencies actually help me think through all variables for the ideas/problems/opportunities. My almost 20 years of entrepreneurial experience makes for an interesting cocktail where before I even come into the office, I have already run multiple scenarios in my head. I share it with my co-founders and then we can just push “play” and start executing the script(s) to see which one tests the “best”. At this point in my career, for most anything tech startup related, I have muscle memory that increases my time to market. A heightened sense of success and failure signals to cut down on the testing times (and costs). Stay agile and always be testing!

Opportunities

Thoughts of how you could improve or advance your current project can also haunt your sleep. A big opportunity and rapid growth can leave a mind unsettled and anxious to take on the next day before you even close your eyes.

Neil Patel, Co-founder – KISSMetrics

Neil-patel-web

Source: billionsuccess.com

Growth keeps me up at night. As a founder one of the biggest things that determines how well your company does is your growth rate. For this reason I continually think about it as it is an opportunity.

The way I confront these thoughts is by continually working on increasing the growth rate with my co-founder and team members.

Nick Francis, Co-founder – Help Scout

Francis-quote-web

Source: Venture Nashville

For most entrepreneurs, the answer to that question varies week-to-week or even day-to-day. At our current stage, I spend most of my time thinking about the team: hiring great people, building a culture they are proud to be a part of, and optimizing our workflows so that they create maximum value for customers.

Most recently, I’ve been thinking about our engineering team and what it needs to look like as the headcount doubles this year. What’s the best team structure? How will one-on-ones work? How is the roadmap managed for each team? Thankfully, we have a lot of supporters, advisors and investors that have been through this and are very helpful as we figure things out. But I still lose sleep over it.

First, I try to gather all the information I can. It’s helpful to know how others approached this challenge before and what they did to figure it out. Typically I do this by asking people for advice, reading books and talking to other people in a similar position.

Once I have enough research, I spend some time writing out ideas, then get feedback from people on our team. My first priority is to make sure the approach aligns with our values.

Thoughts or decisions become valuable in our case when they create value for the business. Value can take shape in the form of efficiency, execution (something customers see) or education. The one thing I try to keep at the top of my mind is that nothing in our business is sacred other than our customers. Everything else needs to be up for debate and constant improvement over time.

Melanie Perkins, Founder – Canva

Melanie-web

Source: vebidoo.de

I would definitely say what keeps me awake it is the huge opportunity we are pursuing at Canva – a complete transformation of the design and desktop publishing industry.

I knew as I was teaching students to use incredibly complex design software that the industry was ready and ripe for a huge change. The vision we have at Canva is making design accessible to everyone. We launched just over 18 months ago and are now used by over 1.5 million people. Every day we are hearing from educators, corporates, small businesses and non-profits about how Canva has opened up a new world of design to them. This is so amazing to hear and what keeps me awake is how we can reach more people who will benefit from using Canva.

I think the best way to manage this is always keeping the long-term vision in mind. It is important to make sure you prioritize the activities that will have a big impact towards achieving it, as there are always a million things you could focus on.

I’d also add, persistence and resilience are essential, as things do not always work how you planned. I came up with the idea for Canva over seven years ago, it takes a very long time to realize an idea.

If you have an idea, get started! Get out there and talk to potential customers. Are their needs being met? Is there an opportunity to do things differently? Do you imagine the future  industry will be particularly different from the way it is today?

Once you see an opportunity, plan out what you would need to do to bring your idea to life. Get into it and learn. Figure out what support you are going to need and reach out to the right people. You’ll gain so much from the experience. You just need to take the plunge!

Worries

Founders invest a great deal of energy and time into a project that they are deeply passionate about. Worries and doubts can creep into your mind when something you care about seems threatened. These worries can sometimes come from real and solvable problems. Often they come from something beyond your control. It’s difficult to know and accept your limits, especially when it involves your creations.

Josh Pigford, Founder – Baremetrics

Josh-Web

Source: Twitter

Problems keep me up a night. The way my thought process works is that I essentially break everything down in to a problem that needs a solution, and my brain constantly spins (consciously and subconsciously) trying to find those solutions.

I do my best to get all of my thoughts written out so I can methodically tackle each problem (usually I do this in OmniFocus and Evernote). That’s what most of my day entails…solving problems. When I’m not working I do things that intentionally take my mind off of those problems. Hanging out with my family, gardening, woodworking and reading (fiction only…no non-fiction/business books).

The best way to make the problems and solutions valuable is to take action. Until you put your solution into practice, it’s just theory based on assumptions. Chances are, you made an incorrect assumption somewhere along the way. Throw the solution into the real world and see what happens… then address the new problems that come up because of it. 🙂

Wade Foster, Founder – Zapier

Wade-web

Source: 1millioncups.com

Honestly not too much keeps me up at night. I try and keep a pretty even keel and things are going well.

This flow chart pretty much sums up how I face problems:

flowchart

Focus on what you can solve. Ignore the rest.

Rob Walling, Founder – Software by Rob

Rob-Walling

Source: productpeople.tv

Opportunities and new ideas rarely keep me awake at night. If I see an opportunity I sketch out in my notebook how I might take advantage of it, then think on it for a few days. But it’s not something I worry about.

I have a 48-hour cooling off period for new ideas. When an idea seems too good to be true I write it down and come back to it 2 days later. If I still feel the same fervor I will investigate it further. Few ideas make it that far. But this approach has stemmed the tide of impulsive, and later regretted, domain name registrations.

Problems…that’s that keeps me awake. A toxic customer. A competitor taking a swipe. Cashflow issues.

I manage these thoughts by being aware that they are impacting my mood and behavior. Just the knowledge that they exert some control over my thoughts is enough for me to stop and ask myself: “Why are you feeling this way?” Which leads me down a logical path of trying to assess how bad things actually are.

Writing them down also helps.

Discussing in my mastermind groups is my third approach.

Conquering them makes you better at doing it again. So over time you build your ability to conquer larger and larger crises.

Rand Fishkin, Founder – Moz

Rand Fishkin

Source: wistia.com

For the first 8 years of Moz, it was usually a combination of opportunities, problems, and ideas that kept me up at night. I think for a long while, I had the sense that we could build anything, and I just had to have the right ideas to pull it off. In the last 2.5 years, though, as we’ve reached greater scale and struggled much more with execution than with market opportunities or great ideas, it’s been a lot of soul-searching and regret that keeps me up. I question old decisions, relive the past, fret about the future, and sometimes (foolishly) wallow in feelings of being unable to effect change or have an impact. I wrote about this in a blog post called “Can’t Sleep; Caught in the Loop.

When it was the more addressable stuff – problems & opportunities – I’d often email myself (or team members) very late at night with my ideas. Getting it into a recorded form felt good, and felt like I’d addressed the issue at least enough to sleep. But the more recent sleeplessness isn’t nearly as addressable. I worked for months with a therapist and then a professional coach on those issues, but continued to struggle. A lot of my effort went into trying not to think about things or to shut down my brain entirely (some of the meditation-like tactics of closing off my mind and trying to focus). Those didn’t work particularly well for me, either.

I think part of my struggle is that I feel a need to do something active to address issues, and, both in my last year as CEO and in the past year having stepped down, a lot of those efforts felt futile. What eventually seems to have worked for me is to focus my energy on things I can influence and control. I work with a couple specific engineering teams at Moz these days, and on content, evangelism, and education as I always have. I’ve worked to limit my thinking, my concerns, and my attempts to influence positive change to those, and I think it’s made a difference, at least with regards to my own mental state and ability to sleep.

I still like the practice of recording an issue – if it’s late and I have an idea, I’ll research it a little, email it to myself, or even send a note to the folks at Moz who can give me feedback or implement it. That’s been valuable for me.

Garrett Moon, Founder – CoSchedule

Source: Matt Report

In the early days, I wondered if anyone actually cared about what we built, or if we’d already signed up the last customer who was willing to pay. These thoughts are pretty irrational and actually pretty unhelpful. Most of them are brought on by personal insecurity more than anything, and that makes them very dangerous.

Later on, these worries faded and I actually worry a lot less now. You learn to start thinking about years down the road rather than just a few hours. Big topics, like business model, certain pivots, and team additions can still keep me up at night, but only because I am focused on the long-term implications rather than the short-term concerns.

I deal with this in two ways. First, I believe in a God that has ultimate control over what happens here on this earth. This allows me to approach things differently. I can’t control everything. In most cases, I can’t control anything. This mindset lets me off the hook. I don’t have to do it all. The weight isn’t on my shoulders. I am just here to do the best that I can with the ability I’ve been given. After that, I’m sort of along for the ride.

Second, I continually remind myself that I will make mistakes and that all I will need to do when that happens is to change my mind and fix it. I think it is actually very difficult for a conscious person to completely screw it all up in an irrevocable way. You probably won’t break anything you can’t fix. So, that really helps keep it all in perspective.

I don’t know that turning doubt and worry into value is the key to success. Rather, I think it is about learning how to cope properly with your worry. It’s about understanding yourself, and where your control and ability ends. You can’t do it all. Realizing that is a huge step in the right direction.

Smart businesses are always going to be looking forward and trying to stay ahead of things. That’s good. You have to have big hairy audacious goals. But, you also have to have the ability to wing it, and roll with the punches. This is the mental game. Keeping yourself (mentally) healthy in this way can solve most problems. It also helps to have a good support system like mentors and friends who can give you the right kind of advice. Or, even-better, tell you when you are being just plain dumb.

Conclusion

Knowing when to quiet the mind and relax is a difficult skill for many idea oriented entrepreneurs. Especially when it’s their great ideas and passions that got them to where they are now. We can learn from these startup founders and their methods for controlling and harnessing this energy in a productive way.

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About

Kyle is the founder of Conversion Cake . He is the author of "The College Entrepreneur" A book for students who want to break into entrepreneurship. Follow him @kylethegray

  • Awesome post Kyle. Thanks for including Billionsuccess.com in the mixed. It was really cool interviewing Neal Patel. Learned a lot from him. Keep up the good work sir.

    • Thanks for reading Herbie! I agree, Neil is an amazing mind to learn from!

  • Thanks for sharing. I’ve found that staying up all night worrying about problems doesn’t get my anywhere except too tired in the morning to be productive.

    • Thanks Emily! I have had the same problems before too. That’s one of the reasons it was so fun to research this post. It’s good to know you’re not the only one with the problem.

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