#40: Questions and answers

Remote work, daily routines, $$, empathy, and more

I’m making this issue free to anyone, not just loyal paid subscribers. It’s different than the typical issue, but gives a flavor of The Inner Game of Startups. If you like it, subscribe! It’s like a dollar per issue, and I pour at least two dollars worth of effort into each. ;-)


Today I’m going to answer a bunch of questions you sent me. (Thanks!)

This should be fun. I love answering questions. It helps me consider things I otherwise wouldn’t, and in the process of answering I learn things about myself.

Let’s jump in.

What do you think about remote work as a CEO? Is your answer different for a startup?

I recently responded to a reporter asking why I hire remote workers. I said the question struck me as backwards. Having an office to pay for, where everyone is forced to commute to, and limiting your talent pool to only those able and willing to be within a few square miles of that office and routine seems far more unreasonable.

I think the burden of proof is on having an office, not the other way around. I’ve worked remotely and in person for two large organizations and two small ones. I have had a remote startup team and an in-person one. But for the majority of the past 15 years, I’ve been remote, and the majority of Praxis and Crash have been.

That’s because I think it works better for us.

I had a colleague that used to say remote work doesn’t work for everyone, because some people just can’t get enough done without the discipline of the office. I laughed. Not least because he seemed to socialize all day at the office instead of work. Anyone who can’t be trusted to focus and work remotely is not focusing and working in the office. They just get the benefit of the doubt because there are visible, physical trappings of work.

Remote work is more demanding. It requires better communication, higher levels of dedication, and a higher level of self-management. In other words, it requires things that are ideal anyway.

It’s possible that new hires with no experience or acculturation do better in person for the first few years. I won’t rule it out. I used to be pretty convinced of it, but now I find even that unlikely. The kind of hire that needs to be in person to be their best is probably not the best hire.

I think this is more true, not less, for an early startup. Early startups can’t afford any marginal team members. Everyone needs to be bought in, sold out, and good enough to not need constant camaraderie to keep focused. A larger company that can handle some semi-committed “meat and bones” type employees may benefit from in-person immersion. But for us, it’s more trouble than it’s worth.

This has nothing to do with viruses. In fact, now that everyone is Zooming in place of human contact, staying distant from each other, and wearing masks like criminals, I have never been more interested in human contact. For the first time in 15 year, a physical office is attractive to me, if for no other reason than to resist the evil of eyeing other humans with suspicion, living in fear, or pretending humans can go on without contact and closeness with one another.

But that’s probably the rebel in me.

I'm in my early 50s and my IT job was just outsourced to India. I've been more on the management side of things than on the actual tech or coding side, so I'm not really up to speed on the latter. How can I reengage and find a new, fulfilling career in this field?

Tough question. It’s so different for each individual, but I’d start asking myself more questions.

What’s most important? Fulfilling work? Pay level? Getting a job ASAP? This may alter the strategy.

If you want to learn to code, it’s never been easier. Go consume all the free courses you can, and most of all start coding. Ask friends who code for help and review. Learning anything technical and artful is best done with friends to compare notes with and pick up tricks from. I’ve never learned to code, but when I learned guitar as a teen, there was a gaggle of half a dozen guys I hung out with all learning at once. Some were better than me, and we all had different styles and approaches and picked up different techniques. When we’d get together, we’d swap hacks and tricks and challenge each other and spur each other on.

Here’s the key that made that possible: we weren’t studying guitar, we were playing. We tinkered and tested and had the instruments in hand as much as possible.

I suspect learning to code is similar. Give yourself little challenges. Build something easy. When you hit a bump, go find some people you can ask for help and show what you’re trying to do. Then keep ratcheting up the difficulty of the challenges.

But I suspect learning to code well enough to get hired as an engineer will take time. You may need to get another job in the meantime while you work on it.

A good way to approach a job that doesn’t require the same level of technical mastery is to focus on your management and soft skills. A coder who can’t code well isn’t very valuable. But a manager, or QA person, or product person, or customer success lead, or sales person who has even a little technical ability is very valuable.

And, of course, hop on crash.co and dive into our playbook for finding the right roles, building a beautiful pitch, and running your job hunt like a sales process.

How do you plan your daily/weekly routine?

This might sound weird, but I don’t.

I mean there’s definitely structure. A few (as few as possible) recurring meetings provide a cadence to the week. And I (mostly) treat the weekend the old fashioned way like two days off work (I never used to, but four kids whose friends all treat the weekend that way kinda force my hand. I dislike work/life distinctions mostly, but alas, I’m not a single guy so I’ve given in to hyping Friday nights like the plebians;-).

My days and week are pretty efficient, and I rarely ever get behind on work. I’m pretty ruthless and can work very fast in spurts when needed. And in 2020, with all my crazy health stuff disrupting everything, I’ve needed lots of rapid make-up spurts.

I don’t “plan” per se, but my days and weeks end up having a pattern anyway.

I don’t set an alarm. That was a personal goal of mine ten years ago, to go to sleep when my mind wanted to and wake up when my body wanted to. I have achieved it. It feels great! So I tend to wake up between 7-8am, depending on the season and amount of sunshine.

I usually go downstairs, make a meat-shake from cow organs and bone broth, and take a cup of coffee back upstairs to my desk. I turn on some meditative music and write my blog post for the day. Then I go through my emails, Slack messages, Voxer messages, and any outstanding tasks from the day before (usually on the sticky note app, a calendar event, an email to myself, or Trello). I review what’s on the calendar for the day so I can be mentally dialed in for calls and podcasts ahead of time. I review my go-to spreadsheets like budget and cash-flow and user metrics. I sometimes pop on Twitter for a quick recap, but the best mornings I don’t.

Then it’s into the work of the day. Calls, meetings, customer support, content creation. Lunch is always a different time, whenever convenient. Same for my walk. I take a walk every day (usually around once a week a day gets too crazy and I don’t get my walk in.) I walk a two mile loop in our neighborhood, sometimes winding longer, so it ends up being 30-60 mintes. Sometimes in silence, sometimes to a podcast or audiobook, sometimes to music, and sometimes doing calls or Voxes. I try to mix up my walks about half work related thinking/listening/talking, half totally un-work related to clear my head.

During and after my walk, I try to spend an hour or two each day on some bigger vision and strategy level stuff. Lots of writing and re-writing documents, whiteboarding stuff, studying the industry, and thinking long-term biz model, positioning, etc. Most of this never goes beyond that, but the best stuff bubbles up and gets shared with the team and sometimes the wider world.

Afternoons are heavier with meetings than mornings (on purpose), and by the time I get off meetings later in the day my inbox and Slack have gotten behind again (partially because I work with so many West-coasters who do their work when my day is wrapping up). I try to be officially done with sitting at my desk by 5-6pm each day so I can play with the kids during dinner prep, eat, relax, and help put them to bed. But I normally pop on and off my phone for messages and stuff during that time, and sometimes do an hour or so of work after the kids go to bed. Heather and I watch something or read, I get in bed around 10pm, read my Kindle until I fall asleep.

But that’s mostly how it turns out, not so much a deliberate plan. And I go through phases where I test and experiment with all kinds of different schedules.

Talk about the 20 year, big-hairy-audacious vision for Crash.

I want to launch MILLIONS of careers, and help millions of people find great jobs.

I want Crash to be a household name, pitching to be the default approach to winning jobs, resumes and applications to be dead, and people to use Crash as a verb. “That company is awesome. I’m gonna try and crash a job there this weekend.”

I want to have redefined the entire career game and what it means to be an employee. I want to create a world of people with a co-founder mentality. People who take ownership of their career and each and every company they partner with. I want to change the concept of earning a paycheck to the concept of creating value and gaining value in return.

I want the effect of this new approach to building a career that makes you come alive to trickle down and redefine how people use their time and resources earlier in life, making status-seeking prestige-based education irrelevant. I want people to be learning out loud and building a body of work from an early age, angling how to crash opportunities.

And I want to build a company worth that begins with a B.

What role if any does empathy play in your leadership role?

None you sissy bastard!

Lol. Just kidding.

The question caught me off-guard. The word empathy makes me think of being kind, approachable, and feeling bad for everyone. In that sense, the main role it plays in leadership is diverting focus from what matters and becoming blown by the winds of others. Not good.

But that’s not really what empathy is. Empathy is an ability to understand what others are feeling. In that sense, it is crucial for a leader.

The Last Dance, which was of course the greatest docuseries in history, reveals a Michael Jordan who led by challenging his teammates and being intimidating and harsh. I get inspired by that. Kobe Bryant morphed into something similar mid-career. My friend TK told me about a decade ago I needed to unleash my inner Mamba. He was right.

I’m not naturally as prickly as Michael or Kobe, but I have found the more willing to be an asshole I am, the more effective and successful I am and the better leader.

So what does that have to do with empathy? It depends. Being an asshole is not the opposite of being empathetic. It can be, and when it is it’s not effective. But it doesn’t have to be.

You can understand what others are feeling and at the same time rise above letting that dictate your own mood and actions. You can sense sadness or lack of motivation, and instead of adjusting your vibration to match it, respond by issuing a challenge. Sometimes being an asshole is exactly what the other person needs.

So empathy in the sense of being in touch with what others feel is crucial. And letting that inform what they need. If what they need is something you aren’t good at providing, don’t try. Instead, find someone who can. Reading people effectively, knowing the seriousness of their feelings, and knowing when you can and cannot respond in a productive way is huge.

But it doesn’t often look like soft, fuzzy, compassion. At least not for me.

If Crash had an extra $1M in your account, what would you do differently? How often is the constraint not having the resources to do what you want, vs not knowing what to do even if you had the money?

This is a great question.

It’s easy to let yourself off the hook by pretending lack of money is the biggest constraint. In the earliest days of Praxis I was tempted to think that way many times. We were so tight and scrappy and my vision was huge. I just needed the resources to execute it!

But having huge visions is not the same as having a specific use for a finite amount of resources.

When you don’t have a lot of money, you tend to think about the infinite number of things you could do with “more”, rather than just the next activity you’d do with the next marginal unit. So with “more” money, I could talk all day about what we’d do. But with the next $1M, it gets trickier. Trade-offs come into play.

When I asked myself this with Praxis, it focused me and revealed how little I knew about what I was doing. I was thinking of raising money at one point, and asked myself, “What would I do with $1M?” I couldn’t settle on any one specific activity. That’s how I knew raising money was a bad idea for us then.

It makes sense when something is working and you know it could work faster and better with more money. For example, if customers are pouring in and more staff could help handle them. Or if ads are driving cost-effective leads and a bigger ad spend could speed growth.

I think money is the constraint far less than we imagine it is.

That said, if Crash had another $1M I have zero hesitation in what I’d do.

I’d add engineering talent so Dave could muster his army and crank through product updates and fixes much faster.

I might add some sales and customer support talent, but only as customer demand began to exceed our current capacity.

I’d also extend our runway by another 12 months or so.

Crash is pre-revenue, so for us, it’s not just a matter of wanting to be able to do more stuff with more money. The most valuable resource is time. I’m 100% convinced if we had three times the runway we do, we’d absolutely nail PMF and build a badass business. With 2x our current runway, 90% chance we do it. The odds decrease as our time to get it right decreases.


Thanks for the questions. It was fun to mix it up this week.


PS - You don’t need a special request to send me questions. I love them, so hit me anytime.