I was at TaskRabbit, where I served as VP of Technology for more than seven years before launching my current company, Guideline, which simplifies 401Ks for employers. As a second-time founder, I’ve begun noticing all the choices I made building my first startup that were actually someone else’s idea.
Now that I’ve founded two venture-backed companies I know you don’t need to conform to the status quo and standard methods. In fact, the more you can think about topics in a nuanced way, tailoring them to you, the more successful your company will be.
Here are a few of the areas I’ve tackled.
As a founder, it’s a mistake to aim for a structured work/life balance, in my opinion. Life has so many intricacies that any sort of assumed consistency, even if it’s just “two hours here, then two hours there” is setting yourself up for disappointment. Your work and your life are unique, so your methods and solution should be individually tailored to account for that.
Adjust for your own status
I have two young kids. That makes work/life balance dramatically different than it was when I was single and in my early 20’s. Some founders set rules like, “I won’t work past 6pm,” but what if working until 8pm one evening means I can delay going to the office until 10:30am the next day to attend a school event?
It’s unsustainable to try and live by a rigid structure in the unpredictable world of a startup. If a more flexible structure will help me build a better business and have more time with my kids, shouldn’t I do it?
When you become a founder, you give up the notion of typical working hours. The stereotypical work/life balance is never going to fit your specific circumstance, so I suggest you build your own.
For me, work/life balance is about mindfulness. I try to be completely present in the moments that matter to me. That moment might be an early morning run over to my daughter’s school to completely immerse myself in her Halloween parade for an hour. I turn my phone ringer off because even though some founders think they need to be accessible 24/7, in my experience, it’s pointless. Solving an important problem over the phone in real time while you’re trying to do something else isn’t a realistic goal.
As an entrepreneur, you have to accept the trade-offs. And if you’re a parent, you may need to recognize that the choice is often “Playtime, dinner, or bedtime?” Personally, I love being the happy smile that starts my children’s day, and I try to be there for bedtime whenever possible, too. This can mean I miss the middle. You can’t do everything. You’re building a company. Don’t beat yourself up if you’re not home right at 5pm, but make the moments you are present count.
I find this approach much more successful than saying, “I’ve been at work for 8 hours, so I need to go home immediately to see my kids.” Don’t mentally transform something you love into a societal obligation.
Founders make decisions for a living. Making (and learning from) mistakes is an inevitable part of growing a company, but improving decision-making should be a primary goal of every founder. Here are three strategies that work for me:
Slow down to make better decisions
Guideline is growing fast—our new plan count has grown by 129% year over year, giving us 10 percent market share of all new 401(k) plans in the country—but moving fast doesn’t mean we make fast decisions.
Many people think they’re great at instantaneous decision-making, but the data shows the exact opposite is true. While I do make some decisions quickly, if it involves an OKR (objectives and key results) or may affect a key business metric or goal, my decisions are not made on the spot. Decisions are almost always better if you wait 15 minutes, and almost every decision can wait 15 minutes. As they say, “Slow is smooth and smooth is fast.”
As Guideline’s CEO, my gut has been very strong, but also very wrong. In some cases, a problem arises and my instinct may be to come down aggressively on the person at fault. When I slow down and unpack the problem, though, the answer usually isn’t so binary. As an entrepreneur, I have the autonomy to design the process and outcome: Would the company be better off if we showed the person what success looks like? The answer is usually yes.
One of my most effective practices is writing down my gut reactions to review 15 or 30 minutes later. It’s much better for the company if I reflect and say, “I’m glad I slowed down” than it is to make a mistake and say, “I wish I’d have acted slower.”
Figure out how you learn best
Every decision is based on information that you process beforehand. To truly improve decision making, you need to first understand how you best absorb data.
Most people gain understanding linearly: they grasp 25% of a topic the first time they hear it, then another 25% the second time, a third 25% the third time, and entire knowledge after something like four repetitions.
Personally, I understand 0% the first time and 100% when I hear it again. I’ve tested this time and time again, both institutionally and personally. Since I need to hear something twice to understand it, I build that into my regimen. When somebody comes to me with a problem, I’ll repeat that problem back to them as a quick way to get that second exposure.
I’ve also noticed my mind benefits from taking time to digest things. As a twenty-something first-time entrepreneur, I didn’t have as much cognitive awareness. Now, I’ve structured my whole process around how my brain naturally works so I can be my most productive self.
When I compare my experience co-founding TaskRabbit to my current role at Guideline, I often find myself reflecting on something Jeff Bezos has become known for:
If you bring me a problem and I need to make a decision based on opinion, my opinion is always going to win. But if you bring me the data, then the data is always going to speak the truth.
Creating a story from scratch is both ineffective and effort-intensive; starting with data provides a solid foundation for making sound decisions. When I take data into account as it relates to a situation or decision, I think much less, which frees up my mind for bigger, more difficult tasks.
Question the horde mentality
Silicon Valley can be an echo chamber where everyone listens to the same podcasts and reads the same books. It’s important to question this horde mentality. You should evaluate each piece of advice based on your specific circumstance.
Figure out what works for your company
It’s an often-repeated adage that startups should “move fast and break things.” This comes from Facebook, and has been applied in far too many circumstances, even coming back to bite Facebook itself.
Since Guideline is in the retirement space, let’s hope we don’t break things! Our value to customers is predicated on providing a solid foundation for company benefits so they don’t need to worry about them. If we push out updates without a solid QA and break someone’s retirement portfolio, we’re undercutting the value that makes customers choose us in the first place. Of course, bugs and breakages will happen, and in those cases, what’s most important is responsibly fixing them with accountability.
Similarly, many founders think their company should be growing at all costs, but that approach, as even Paul Graham reminds, is not necessarily true for every business. Instead, it’s important to make decisions that are right for your circumstance and have systems in place to check yourself. We call it responsible growth.
Keep yourself honest
It’s easy to get caught up in bubbles and the weird pseudo-celebrity thing that happens in the valley.
Are you building a startup to hit the front page of TechCrunch, or are you building a company you’re truly passionate about?
I won’t name names, but it’s easy to look at many startups and find it hard to believe that they truly care about the solution they’re building and the problems—or lack thereof—it’s solving.
Having internal truths and building something that matters will keep you grounded through both the good and the bad. I recommend running internal checks on yourself. Personally, I ask questions like:
- Is this what I want to be doing?
- Is this how I should be doing it?
- Do I truly believe in doing it this way?
When I moved to San Francisco in 2010, it felt like everyone was glued to TechCrunch. New startups were coming out left and right, creating very distracting hype cycles, so I found myself focusing less and less on my own company. Staying true to your own core personal truth is fundamental to building something that’s not just successful but impactful.
Young entrepreneurs, in particular, can easily get caught up in the hype. It’s hard to stay humble when you’re on the front page of a tech blog time and time again. It’s much easier when you have trusted people around you who keep you humble. Whether it’s a therapist, fellow founder, spouse, girlfriend, or boyfriend, everyone needs a reality check every now and then.
Many founders claim to be 100% mission-driven, but I think that’s naïve. If we’re being honest with ourselves, there’s always some personal objective that drives a person to succeed—and that’s OK! While I want to make sure everyone has access to an amazing 401(k), I also want to set my kids up so that they have all the opportunities possible.
When I see them at night, in whatever scenario that may be, that grounding allows me to ask myself, “Did I move the company forward? Am I helping both the world and myself?” I can tuck my kids into bed and remember why I’m going through the struggle of starting a company. Then, the next day, when I wake them up, that connection gives me the power to do it all again.
I urge every founder out there not to let the bevy of advice and information distract from what makes sense for you or your company. Instead of investing time reading what other people are doing, take the time to figure out how you work best.
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