In 2022 I ran experiments with:

• Hiring an asynchronous tutor to go deep on a technical topic
• Removing phthalates from my life to improve health and fertility
• Dramatically reducing phone usage for more productivity + happiness

At the end I’ll also share some quick wins I discovered this year to:

• Significantly improve jet lag
• Reduce hangovers
• Understand your current health more deeply

For each experiment, I’ve laid out what I tried and what worked (and didn’t). Check out whichever ones interest you, and let me know what experiments you suggest I try in 2023! 😎

Hiring an asynchronous tutor: Thanks to a friend red pilling me on the remarkable progress of AI early this year, I did a deep dive on machine learning and large language models. But when I first (attempted to) read the canonical paper that unleashed this latest wave of AI I realized I needed a much deeper technical grounding. Reading a few blog posts was not going to be sufficient.

What I tried: A friend and I hired a machine learning PhD and created a chat group with our tutor and a few entrepreneurs and investors who wanted to uplevel their technical understanding of the latest breakthroughs. Instead of having weekly scheduled lessons (I hate meetings…) all the tutoring is async — each of us reads papers and drops in questions for our tutor. We pay our tutor a fixed fee per month and he responds to our questions at his leisure.

What worked (or didn’t): This has been an incredible way to learn and I plan to use it anytime I’m going deep on a topic in the future. What was particularly helpful:

• Before I had the tutor in place, I would read a blog post (like this explainer on transformers) and I would grok parts but there would be large areas of confusion. With the tutor in place, I would simply do a deep dive on my own, write down all of my questions, and then get answers from our machine learning PhD to fill any gaps.
• I also found it very helpful to read a paper, type up my own summary of the key insights, and then share it with our tutor to have him assess whether my summary was fully accurate.
• I ended up learning as much from the other participants in the chat (not just the tutor) from the questions they asked and the research they shared. And, yes, once ChatGPT launched I would often go to my friendly machine assistant to answer my easy questions before I went to my live tutor.
• One thing I would do differently next time I create an async tutor / chat group like this is have a set curriculum that everyone needs to read before they can join the learning group. People came into our group at different levels of technical depth, and the group would have been even more efficient if we forced everyone to read a common set of foundational materials.

Recommendation: There’s a Ben Franklin quote that goes something like “a person who teaches himself has an idiot for a teacher” which is exactly how I feel for not having tried this earlier. I will be leveraging this new learning method aggressively going forward. 👨‍🎓 (If you have an assistant with Athena, we’re working on a delegation playbook for this so you’ll just be able to say “I want to be async tutored in X” and your assistant will handle the rest. Team will have this production ready in a ~month.)

Removing phthalates from my life: You may have heard that male testosterone levels and sperm count have been falling 1% per year for decades: the average 25 year old male today has about the same testosterone level as a 45 year old just two decades ago. Miscarriage rates have likewise been increasing 1% per year. Why? Exercise, nutrition, and obesity are obvious drivers, but Dr. Shanna Swan, a reproductive epidemiologist, argues persuasively that there is an additional, hidden cause: the presence of phthalates—a chemical manufacturers use globally—in our lives. Phthalates are endocrine disruptors which means they change our natural hormonal levels. The good news is that for adults, if you remove phthalates from your environment, your hormones will return to normal quickly, sperm count will improve, etc. However, for babies in the womb and children <2 years old their fertility can be impaired forever. This very much caught my attention.

What I tried: Tbh, if I couldn’t delegate this easily, I probably would have listened to the Shanna Swan interview on Rogan, been shocked by the data, and then…done nothing. Phthalates are everywhere — not just in plastics but also in soaps, cleaning products, food packaging, clothing and almost everything that carries a fragrance. Figuring out how to remove these things from your life is hilariously daunting. But since I’m lucky to have a team of Athena EAs supporting my crazy delegation experiments, here is what I did:

• I asked an EA to read Shanna Swan’s book Countdown for me. (Yes, I sometimes delegate reading books. 😂 I highly recommend!)
• While the EA read the book, I asked her to make a spreadsheet and note every type of product that has phthalates in it. The list is really, really long. 100+ items across food, kitchen, bedroom, and beyond. 😅
• I then asked my EA to order replacements for dozens and dozens of replacements items — glass storage containers instead of plastic for food, soaps and shampoos, stainless steel bottles and plates for 2 year old instead of plastic, organic cotton underwear, and on and on.

What worked (or didn’t): Removing plastics and phthalates more generally from your life is an absolutely insane undertaking. We got rid of maybe ~50% of offending items with our first purging/purchasing wave but for *literally* months we continued to find stuff that needed to be replaced. For example, just this week I discovered there are phthalates in most tea bags. 🤯

• Getting to 0% exposure is impossible, and shouldn’t be your goal, but even following the 80/20 rule is a real amount of work. But we’ve now mostly cleansed our life of these toxins which feels good!
• I was mostly motivated to do this to protect our kiddos bc phthalates cause permanent fertility damage for kiddos <2 years old. But I also measured my free testosterone at the end of this experiment and it was 10% higher than my previous measurement — lots of moving variables with testosterone but that was cool to see.
• If I could do this again I would have taken this test to measure my phthalate exposure pre/post experiment — that’s the best way to see how many toxins you’re removing from your body.

Recommendation: This was actually such an absurd undertaking 😂 I can’t recommend anyone try this on their own unless you are pregnant or have young kids. That said, removing phthalates is an important driver of health and fertility so my friend Justin Mares and I are are incubating a new startup that will productize this experiment. Our goal is to create a simple and seamless experience to remove all the phthalates from your life. Just as the gluten-free wave in the 2000s created $100M companies like Udi’s we believe the phthalate-free wave will be big in the 2020s. If you’re interested in being an alpha customer for this new company, or want to get involved, ping either Justin or me.

Dramatically reducing phone usage: I’ve run experiments to reduce phone usage in the past, like last year’s freedom phone. I highly recommend having a freedom phone but I still check my phone more than I want so I ran two new experiments this year. My goal here isn’t to work less. Rather my goal is to 1) work more productively (computer > phone) and 2) break the habit of casually picking up my phone. My theory is that total time on your phone is not a problem (e.g. making a long phone call to a friend is great), but the unnecessary pickups (e.g. wonder what new messages I have…) are not aligned with health and happiness.

Experiment #1: The first experiment I ran was to see if I could reduce phone pickups by 2/3, going from ~55/day (which is once every 15 min) to 15 per day (roughly once per hour). To reduce pickups I tried three things: 1) I start each morning by going to my desktop and don’t pick up my phone. I tackle all my messaging apps via Texts. 2) When I exercise I bring my freedom phone instead of my regular phone. 3) The rest of the day I try to use my willpower. Lol. 😅

What worked (or didn’t): This was harder than expected. With the 3 efforts above I was able to reduce phone pickups by ~30% but it didn’t feel dramatically better. And it felt like work. But while doing this experiment I had a useful thought — why do I ever use a phone at home? If I’m inside my house shouldn’t I exclusively work on my desktop (10x more efficient than phone)? I tried this for a single day and discovered I needed my phone to turn on Sonos at home, to receive a two-factor auth, to check baby monitor, etc. And once you use your phone to turn on Sonos…Whatsapp is just a click away. Which led to the next experiment…

Experiment #2: With the insight from above I realized the more radical way to break the phone-pickup-habit is to have 2 separate daily use phones.

• Home phone: The home phone is basically a remote control for your home — Sonos, baby monitor, etc. It’s also where my 2FA goes for logins. It has zero messaging, email, or productivity apps. You can use it to turn on Sonos or get 2FA but you can’t get distracted. If I want to email or check Whatsapp, I am forced to do it on my computer.
• Outside phone: The outside phone has Whatsapp which is a core communication app for me, Superhuman for email, Athena app for sending delegations. It doesn’t have any “I can read later” messaging apps like Telegram (I can check those on computer when I’m home).

I’m just kicking off this experiment right now. The plan is to have my home phone sitting at my desk in my office, and the outside phone sitting by the front door so I only pick it up on the way out of the house. This is an admittedly aggressive plan for slashing phone pickups, but I think it will both increase my productivity (way more work at computer) and make me happier and less addicted to picking up my phone. I’ll report back on the results next year.

If you want to check your own pickups + phone usage on iOS go to Settings → Screen Time → See All Activity → Scroll Down.

Those were the more time-intensive experiments I ran this year but I also tried some things that were quick wins that I highly recommend:

• Significantly improve jet lag: If you travel 3–4 time zones it’s not a big deal, but 6–12 time zones can wreck your productivity for days. Fount.bio has a jetlag kit that is $100/flight and really works. They give you a protocol that is personalized to your flight and you simply follow the instructions in the app during your travel day. It’s a combination of tinted glasses and supplements you take every couple hours. On my last 6+ time zone trip I was able to adjust in a single day.
• Reduce hangover: I hesitate to share this because it works too well 😂 and we’re all better off not drinking. But assuming you are drinking: Zbiotics has created the world’s first probiotic that prevents hangovers. You take one shot glass of the liquid as your first drink of the night and then drink as usual. I’m not saying this will make you invincible, but the 3 times I’ve used it it has been remarkably effective. HT to The Next substack for recommending.
• Understand your health more deeply: I’ve been looking to do a deep dive on my health and fitness for a while. I explored various options, like Mayo Clinic Exec Health Program, but they were all too limited. I wanted a full body + mind deep dive that I could use as a baseline for my health in the decades ahead. I found it: Biograph. You show up for 6 hours at their clinic for tests including full-body MRI, VO2 max, blood tests, flexibility tests, mental tests, and more. A few weeks later you meet with a doctor, nutritionist, and personal trainer and review all your results and make a game plan for optimizing your health. My health and fitness is already pretty dialed in but I still found things to improve. This isn’t cheap but it’s incredible well done and I highly recommend.

That wraps my 2022 life experiments. 😎

Happy holidays everyone!

PS-For Athena clients reading this, our team is working hard to turn a number of the experiments above into delegation playbooks that will be available sometime in 2023. They aren’t ready yet but stay tuned. :)

• How do I get a raise?
• Why do I have a manager now?
• Are you going to fire him?
• How do you decide if I’m a top performer?
• Why was she promoted and not me?

Your answers will determine how quickly and effectively your team executes.

In the first phase of a startup you focus on building a product that customers love. During this phase, the team (typically <10) should work quickly and informally. You are a team hunting for a business — flexibility and speed are key and unnecessary process just slows you down.

When you find product-market fit, you enter the second phase: scaling your business and team. Process is now required for you to move fast.

You can answer the questions above in one of three ways:

1. Ad hoc: Tackle issues as they arise. This works well at the seed stage, but it creates chaos when your company is scaling from 10 to 100. 🤯
2. Comprehensively: Build processes for anything you can, and work through edge cases ahead of time. This works when your team is 1,000+ but will strangle your company if applied too early. ☠
3. Philosophies: Create a framework with high-level philosophies on important processes, but don’t worry about edge cases. This is best for scaling from 10 to 100. 🚀

Company philosophies can help you bridge the gap from the hunting phase to the scaling phase. They go a level deeper than company values but can still be read in 5–10 minutes.

Below I’ve included a roadmap for how you can create your own company philosophies, as well as a template/example set of philosophies I developed with our team when we were scaling from 10 to 100+ employees.

Scaling will always be hard but creating company philosophies is one of the best tools for scaling faster, more effectively, and with less drama. Don’t worry, you’ll still have plenty. 😉

How to create your own company philosophies

You can go from brainstorm to launch in <1 week:

1. Brainstorm (1 hour): With your co-founders and team, write down a list of issues that are slowing you down or you expect to raise lots of questions in the year ahead. What questions have you had to answer more than once?
2. Draft (1 day): For each issue, draft with your co-founders a company philosophy that will help your team work quickly and effectively together. The goal is not to cover every corner case but instead to create a framework you and your team can use for 95% of situations.
3. Feedback (1 week): Get feedback from your team, investors, and fellow entrepreneurs. When in doubt, simplify. For a team of ~10 a one page philosophy is sufficient. It will grow to a few pages as your team approaches 100+.
4. Launch: Launch v1 with your team and set a regular cadence (e.g. every ~6 months, depending how fast you are scaling) to review and update. Philosophies are a living document that evolve as your team grows.

Company Philosophies [A Template]

We want to build a company and a product that touches a billion+ people. To do that, we need to build an amazing team. There are lots of decisions we’ll make as we scale our team, so we’ve created this document to lay out the philosophies that will guide those decisions so we can scale quickly and consistently.

Philosophy on Compensation

We pay fairly. You have significant upside. We have an inspiring mission.

We pay fairly: We pay competitively compared to other startups at our stage, and we work hard to ensure people are paid fairly. We look at three dimensions to determine what is fair: 1. performance, 2. impact (scope of responsibility and contribution), and 3. market data for the role. Our focus is on impact and thus individual contributors can be (and often are) compensated higher than people managers.

You have significant upside: All employees are given equity, which gain value as the company grows. These are inherently risky, but if we build the company we all dream of, you get significant upside.

We have an inspiring mission: While salary is a very important part of compensation, we believe other things are even more important: talented coworkers, challenging problems, and an inspiring mission.

Philosophy on Raises

Raises are given for increases in performance and increases in level of impact.

Performance- and impact-based: Raises are performance- and impact-based instead of automatic (e.g. they are not 3% annually for everyone). Raises are meant to reward sustained increases in performance and increases in impact. The performance needs to be well proven before a raise is given.

Process: At the beginning of each year managers to make recommendations for raises. Recommendations will be thoroughly vetted and discussed at calibration meetings with the leadership team to ensure we’re aligned and treating team members fairly across teams.

Bonuses: We don’t do bonuses. Some companies have used bonuses successfully (e.g., Google) and others pay exclusively through salary and equity (e.g., Amazon). We looked at academic studies, talked with other startups, and got feedback from investors and decided against bonuses for now. We believe stellar performance should be rewarded with additional salary and/or equity rather than bonuses. We’ll reassess in the future.

Equity refreshes: We believe team members should always be vesting. The amount of the new grants will vary by employee and depend on the factors outlined above — performance, impact, and market adjustments — and also company trajectory.

[Note: We didn’t create an equity refresh policy until we have team members hitting 4+ years. Until then, we just said “We believe team members should always be vesting. Once we have our first team member hit 3.5 years we’ll create an equity refresh policy.”]

Philosophy on Measuring Performance

Our goal with measuring performance is to help each other grow and have a huge impact.

We measure performance to help each other grow: Measuring performance is critical to helping our team learn and grow. No one here has reached their full potential, and that is why we want to build a culture that continually challenges and supports team members to reach ever higher. For this reason, measuring performance is crucial to our success.

We aspire to be as fair as possible: Measuring performance is an inexact science but we seek to be as objective and fair as possible. We do that by taking a comprehensive approach that does not rely on any single input. We look at all relevant factors (impact, growth, exemplifying our values, etc) and from all directions (managers and peers). Assessing performance is a fundamental skill needed for VP, Director, and Manager roles so we hire/promote carefully and invest in ongoing training for these roles.

360 Reviews: Every 6 months, we have 360 Reviews where team members receive written feedback from their manager as well as a few peers. The primary purpose of these reviews is to help make each other better. 360 Reviews are not determinative of performance/comp. Reviews are just one input in measuring performance along with everything else. We do not directly tie 360 Reviews to compensation because there are many other important inputs to measure performance and because we want to encourage forthright and transparent peer reviews. Even the best peer review should include development areas.

Philosophy on Transfers

We always look for the most capable person, but happily take bets on our team. Applying for a transfer between teams (e.g. marketing → product) doesn’t put your current job at risk.

We always look for the most capable person, but take bets on our team: When deciding whether to promote internally or hire externally we will always look for the most capable person for the position. In many cases we will take a bet on an existing team member because we believe they will succeed in the new position but may not have yet proven themselves (as compared to an external candidate with more demonstrated experience).

Applying for a position doesn’t put your current job at risk: Whether your interest in applying for a position is for a promotion opportunity or you’re interested in trying out a different role, applying doesn’t put your current job at risk. We encourage team members to apply for openings they are interested in. If you decide to apply to another team, you should let your manager know to get their input.

Philosophy on People Managers

We believe people managers should serve their team (and not the other way around).

Our people manager mission statement: Your mission as a people manager is to create a high-performance and highly-engaged team that has a massive impact. You accomplish this by hiring the best and developing them to be even better, by inspiring, challenging and supporting your team members to produce their best work in pursuit of a shared vision, and by embodying our core values in all that you do.

Our people manager values:

Creating a high-performance and highly-engaged team

• Hire the best: You have very high standards for who you hire (high potential, values fit, and chemistry with your team), and you know that recruiting is one of your top responsibilities.
• Build a cohesive team: You align and rally your team around our vision, mission and values and you invest in making your team greater than the sum of its parts by building trust, fostering personal bonding, and having fun.
• Challenge and support: Peak performance is realized when team members are challenged and supported. You challenge hard and support hard. Supporting includes input, encouragement, ensuring they have the tools they need, and removing roadblocks. And you inspire by actively showing your team members how their work connects to our mission and creates major impact.
• Coach your team: You invest time in understanding your team members’ personal and professional goals and spend time coaching and developing them. And you give frequent, direct and real-time feedback, even when it is uncomfortable, to help them grow.
• Praise and recognize: You understand that effectively delivering praise and recognition increases motivation and teamwork. You frequently deliver authentic praise and meaningful recognition to team members, peers, senior leaders, and staff throughout the organization.

Setting the tone at work

• Ambassador for our Values: When you sign up as a people manager you walk into a public spotlight. That means you are signing up to have all your actions become a public example. The respect and gratitude you give our office cleaners no longer reflects on you as an individual; it reflects on our company and all of us. With that comes very high expectations for your character.
• “I’m Third” Leadership: When you become a people manager, you sign up to put our company first, your team second, and yourself third. You display this humility by being willing to get your hands dirty to help your team and by always turning the spotlight from yourself to your team. You display leadership by supporting teams and people managers across the company and by taking ownership of identifying and problem solving issues outside your domain.

Thanks to Jake Zeller and Babak Nivi for reviewing and improving this post. 🙏

In 2021 I experimented with:

• Creating a personal CRM to get 10x more leverage from my network
• Setting up a Freedom Phone so I’m less distracted by my phone
• Kindle-izing all my reading so I have zero distractions on my computer
• Digitizing our nanny so we sleep more (black diamond delegating 😅)
• Scheduling all my meetings on Tuesdays so the rest of my week is flexible
• Delegating by voice only (no email) to increase efficiency
• Moving 95% of my messaging from phone to the Texts desktop app

For each experiment, I’ve laid out what I tried and what worked (and didn’t). Check out whichever ones interest you, and let me know what experiments you recommend I try in 2022! 😎

Creating a personal CRM: It’s a running joke in venture that someone needs to start a personal CRM startup. But it’s a joke for a reason: I’ve tried a half dozen now and they are all terrible. So I finally decided to just build a personal CRM for myself.

What I tried: We took my ~20k contacts and moved them into Airtable. Then we enriched the contacts with ~100 data fields from public/private sources. We added data like: how much venture capital has this entrepreneur raised, how many times have I emailed with the person, how many employees does the company have, how many twitter followers, what companies has the person invested in. Lots of the data could be pulled from LinkedIn and Crunchbase APIs, and some data required more manual data work (e.g. when was my last contact with someone).

What worked (or didn’t): I finally have the personal CRM I’ve been dreaming about. This new setup allows me to execute queries like this:

• What CEOs am I connected with near London who have raised >$50M
• Show me investors I know who invested in Notion, stack ranked by how many times I’ve emailed with them
• Find me CMOs of enterprise startups with >250 employees stack ranked by Twitter followers

I finally have a CRM that allows me to search in the way I’ve always wanted. I’m using my new CRM all the time now. The biggest weakness we’re still looking to solve is Airbtable’s search is exact match only. So right now I have to search things like [title=CMO or Chief Marketing Officer or VP Marketing]. If anyone knows a tool that can make Airtable’s search more flexible, please let me know.

Recommendation: This was my 2nd attempt to build my own CRM. The first attempt got mired in over-complexity. So if you do attempt this yourself I highly recommend you start very simple and add complexity as you go.

Freedom Phone: I tried a phone sabbatical this year — 1 week w/o ever using my phone — and I loved it so much that I decided I wanted to do it more often. But the challenge with a pure phone sabbatical is it is only practical every so often. So to solve this I repurposed an old iPhone into what we now call the Freedom Phone.

What I tried: Factory reset an old phone and then only installed essential apps: Google Maps, Uber, and the Athena delegation app (no sabbaticals from delegating 😉). There’s no email, no messaging apps, nothing that could possibly distract or tempt you. And then the only contact I installed in the phone was Katherine’s phone so that if I need to call her I can and if she needs to find me she can.

What worked (or didn’t): Now when we go on dates we bring the freedom phone instead of our real phones. Or if we go for a hike on a Sunday afternoon we bring the freedom phone. I ended up also installing Google Photos so photos sync with my main phone.

Recommendation: Yes! If you want to be distracted less by email/messages while you’re with your friends this is really effective and yet still practical. I use mine multiple times every week now.

Kindle-izing all reading: Every day I get emailed or messaged a dozen+ substacks or blog posts I want to read. But when I’m working at my computer I want to be in the zone and not be distracted by this endless rabbit hole. So I tried an experiment of not reading anything non-work-related on my computer and instead sending reading to my Kindle.

What I tried: Whenever I receive a Substack or blog post I’m excited to read, instead of interrupting my work I just forward it to my EA. She converts the content into a PDF and then sends it to my Kindle. (Every Kindle has a dedicated email address you can send PDFs to.) At night in bed I turn on my Kindle and a half dozen articles load up.

What worked (or didn’t): This has been awesome. I used to feel torn when I’d receive interesting stuff to read. Should I be productive on work or spend the next 18 hours reading Dan Romero’s crypto reading he just sent me? 😅

Recommendation: Yes. I’m way more productive on my computer, and every night my kindle is full of amazing stuff to read in bed.

Digital Night Nanny: When people have kids they have to make a hard choice: Do I have my sleep destroyed by the new babe or do I pay $$$ for a night nanny so we can sleep? People with means will often get a night nanny but only for the first couple months. After that most parents will handle solo — and typically have their sleep interrupted a couple times/week. But Katherine had a genius idea: what if we could delegate this?

What I tried: We nominated one of our most trusted EAs in the Philippines to be our digital night nanny. She was given access to a Wyze camera in the babe’s room. From the app, the EA could see/hear the babe throughout the night. We then put the Freedom Phone (see above) next to our bed at night, and gave the EA this instruction: If the babe wakes up, cries for a couple minutes, and goes back to sleep: don’t call us. If the babe wakes up, and stands up or won’t stop crying: call us.

What worked (or didn’t): Katherine and I went from averaging ~5–7 hours/night of sleep to ~8–9 hours/night of sleep. Game changing! Our babe wakes up a couple times most nights and cries for a few minutes each time. This used to destroy our sleep. Now we only wake up when we’re actually needed which is very rare. When we first ran this experiment we just used our regular phones — but that means if you get a random spam call in the middle of the night you’re waking up. So we now use the dedicated Freedom Phone which no one has the number to except our EA.

Recommendation: A night nurse costs $200–300/night in most places in the US. That’s crazy expensive. But because our EAs are working in the Philippines they are already awake during our sleeping hours. And because they can do their regular work — with the babe monitor on in the background — we’re now getting 365 day/year night nanny coverage for no additional cost. This has been one of the greatest delegation experiments of our life. All credit to Katherine, and our amazing EAs in the Philippines. 🙏

Tuesday Meeting Day: In a previous experiment, I was successful at moving 95% of my scheduled meetings to asynchronous conversations (e.g. more voice notes on whatsapp). But meetings are still necessary for a few things. So to build on this experiment, this year I tried only scheduling meetings on Tuesdays. The rest of the week is for focus, deep work.

What I tried: Tuesday is my meeting day. No meetings on any other day.

What worked (or didn’t): I love having multiple days a week where I can focus on deep work without any interruptions from meetings. The trade-off is my Tuesdays are sometimes very long (e.g. 10 hours of back-to-back meetings) but for me it’s worth it because I am multiple times more productive when I have long stretches for deep work.

Recommendation: This isn’t for everyone — if you’re hyper scaling a startup as CEO you’ll probably need more meetings than me — but I’m personally way happier and more productive this way.

Voice only delegation: Delegating to your EA by voice is at least 3x faster (vs email or text). It also allows you to delegate while you are on a walk, at the gym, or jumping in an Uber.

What I tried: For three days I only delegated by voice. No typing email responses (voice delegated instead), no drafting docs (voice), no ordering things online (voice). The goal was to touch my keyboard as little as possible. To do this I used the Athena delegation app. After dictating a delegation, the app sends it to my EA, including an audio transcription, and adds a new task in our Asana project board. For delegating from my computer, I used Loom to make videos.

What worked (or didn’t): Delegating by voice is a muscle you have to develop, and the more you practice the better you get. Like going to the gym, the first few sessions are the hardest and it doesn’t feel natural…but with practice it starts to feel so good. Delegating only by voice really pushed my comfort level — I’ve gotten good at voice delegating email drafts, projects to research, and even outlines for documents I want to write. The level I haven’t unlocked yet — but I have a friend who has — is doing polished, essay writing by voice. This friend has written an entire book by voice. I have another friend who hasn’t written an email for years. #Goals

Recommendation: All of the top 1% delegators I know delegate a significant amount by voice. If takes practice but it’s worth the investment. I now measure my # of voice delegations every week and have competitions with friends to see who can push the limits the most.

Superhuman for messaging. I’ve been wanting a Superhuman-like interface on top of all my messaging apps for years, and I’ve finally found it: Texts. This is — by far — my favorite new productivity app. I’ve moved 95%+ of my messaging off my phone because Texts is so much more powerful. Every morning for me now starts with Superhuman for email + Texts for messaging. The product is still v1 — it’s still a little buggy — but it’s increased my productivity dramatically and I’m addicted to it.

That wraps my 2021 life experiments. 😎

If you have suggestions for experiments I should try next year — especially radical delegation ones — please share.

Happy holidays everyone!

If you do it right, it will transform your trajectory. If you mess it up, it will set you back months or years — or worse.

Here’s how to get it right:

1. Forget about traditional interviews. Execs are polished, so it’s hard to uncover their weaknesses in a few hours of interviews. But there’s a place where both their strengths and weaknesses are intimately detailed: 360 reviews. If I’m serious about an exec after a few conversations, I ask them to share their most recent 360 review. I also offer to share mine. I say something like:

I want you to intimately know my strengths and weaknesses, and I want to know yours as well. I will share my last 360 review with you so we can discuss it on our next chat, and I’d like you to share yours with me. I know it won’t be perfect and some parts may be unfair. I’m just looking for you to walk me through it so we can discuss.

No exec has ever turned down this request. If they did, it would be an instant red flag.

2. Scale outbound 10x. Top execs are hard to find. You need to widen your search far beyond what you do for ICs. When I was searching for a new board member for Thumbtack, I sent 83 queries like this to high-value contacts by following this method: 1) Draft an email template. 2) Dictate a voice note with a personalized message (just one sentence) for each recipient, to be included in the email. 3) Task your EA with adding the notes to emails and sending them out for you. Using this method, you can send 100 personalized emails in an hour, instead of 10 hours.

3. Calibrate to the top 1%. Because most execs present well, it’s nearly impossible to extract signal from them unless you’ve calibrated your search against top talent. You need to know what A+ looks like. To do this, ask your investors to name the top one or two execs they’ve ever worked with for the position you’re hiring for (e.g. CFOs, if you’re looking for a CFO). The goal isn’t to meet people to hire, but rather to calibrate your search against top 1% talent.

Here are questions you should ask the top 1% execs:

How do you define your mission as an exec?

Can you walk me through each component of your job in detail?

What qualities should I be looking for in this role?

How should I interview for this role?

Are you open to interviewing a candidate or two so I can calibrate with you?

I struggled for months to find a 10x candidate when we searched for a VP of People at Thumbtack. So I hit pause and calibrated our search by getting to know the best: Laszlo Bock. We leveraged Laszlo for sourcing, interviewing and closing until we found our 10x exec.

Searches for execs last anywhere from 3 months to an entire year. Start early, set your bar against the top 1%, and grind away until you find your 10x exec.

Even if you run a perfect search process, you will still make mistakes. I don’t know a single founder who hasn’t mis-hired an exec. What separates stellar founders from the rest is they recognize these mistakes within the first few months, quickly ask the exec to leave before lasting damage is done, and re-start the process better calibrated the second time around.

For each experiment, I’ve laid out what I tried, what worked (and didn’t), and whether I recommend trying. Check out whichever ones interest you, and let me know what you’ve been experimenting with.

Working without a calendar: I love working, but I hate meetings. Getting into flow takes time, and meetings break flow. So this year I experimented with drastically fewer meetings. Not 20% fewer meetings — but 95% fewer. My goal was to have as many days as possible with zero meetings.

What I tried: First, I eliminated basically all recurring meetings except board meetings. Whenever I got meeting requests, I filtered them in one of four ways: 1) If the meeting actually required a call, I’d ask the person to shoot me a text or Whatsapp. A couple times/week I’d go on a walk, open my messages, and start calling people to connect. 2) If the meeting was necessary but didn’t require a live convo I’d ask the person to send me a voice note via text or Whatsapp with the problem/situation. Communicating asynchronously replaced 80% of meetings. 3) Any meetings that were absolutely necessary to schedule in advance, we’d batch into a block on the same day. 4) I ruthlessly eliminated the rest. For examples, at Athena we instituted a max one meeting per week policy. I also had my EA send me a calendar analysis once/quarter to track how many hours of meetings I had, which helped me get more ruthless over the course of the year.

What worked (or didn’t): It admittedly took some practice learning how to say no to so many meetings. Sometimes I felt bad not being more generous with my time. But, once I got over that, it was glorious! My productivity was higher because I had so much more focused time and so few distractions. And the impact on my happiness was even bigger. The biggest tactical win for me was moving meetings to async voice notes on WhatsApp. I found that 80% of hour-long meetings can be replaced with “send me a voice note on WhatsApp and let’s discuss there.”

Recommendation: If you’re managing a hyper growth startup with a huge team in an office, this won’t be possible for you. But if you can control your schedule, you should absolutely give this a try. You’ll find how few meetings you truly need. And if you’re not persuaded by me, check out Naval, Andreessen, and Paul Graham who all have all personally experimented with + advocated for killing meetings.

Sleeping without an alarm: Sleep is a core driver of health and happiness. But people typically schedule their sleep around the rest of their lives. This year I did the opposite: I never set an alarm in the morning. (Only exception was for a handful of flights and board meetings.)

What I tried: First I read Why We Sleep which lays out the importance of sleep, and how to get the deepest sleep. Then I tried everything the book recommends: don’t set an alarm (ever), keep your room cold (<68 degrees) and dark, use a white noise machine if the room is not totally silent, no caffeine, and no alcohol. In other words, Silicon Valley Mormonism. 😂

What worked (or didn’t): This experiment requires first doing the no-meeting experiment above or never setting morning meetings. But other than that this is about the easiest and most enjoyable experiment you will ever do. I found over time my schedule gradually shifted earlier and earlier towards the hours I’m most productive at work — by the end of the year I was waking up by sunrise without an alarm.

Recommendation: Many people obviously have inflexible schedules (e.g. parents) but if you can control your schedule, you have to try this. It’s the most enjoyable experiment I’ve ever run — I wake up every day rested, happy, and excited to work.

Starting a company without investors, an office, meetings…and lots of things: With Athena I wanted to build a company that was not just a new product or service but an experiment in company-building itself. Most new-company-design experiments fail (e.g. basically every startup that tries to get rid of managers or PMs 😂) but it’s important we collectively keep trying new methods because the winners can drive massive productivity gains across the economy. (To say this more explicitly: I think organizational/company design experiments are typically NPV negative for individual startups but very positive for the ecosystem.)

What I tried: We started Athena with lots of new constraints: we are building Athena with no investors (bootstrapped to profitability), no employees (all hourly/contract/project-based), no office (fully-remote), no meetings (max 1 per week), no 1-on-1s (informal catchups), no 360s (culture of ongoing praise + feedback), no team members we don’t love (only hire people we’d want as friends), and no customers we don’t love (fire customers who are difficult).

What worked (or didn’t): Building a company with so many constraints takes more work upfront. Also there’s a relentless gravity towards the default that you have to continually resist. Resisting this gravity was the hard part. For example, there were dozens of times where people I was interacting with wanted or expected (understandably) a more traditional workplace. But the purpose of putting these — admittedly unusual — constraints on ourselves was to liberate us to work faster and happier. And it worked! In our first year at Athena, we’ve grown the team to 75 amazing people, seven figures in ARR, a customer waitlist that is now 12+ months long, and a sustainable (=profitable) business that we can build for the long-term. And, most importantly, we’re enjoying the hell out of building a company on our own terms.

Recommendation: There are lots of expectations for how to build a company. But the truth is there are many paths to building a massive, generational business: in my view, if you’re going to spend a decade+ on an endeavor, you should design your company to be a place you absolutely love.

Living without a home: When Katherine and I went deep-minimalist a few years ago we eliminated all possessions except what fit in carry-on luggage. We’ve been living for 3+ years now with <100 possessions each. When we first did this I was still day-to-day at Thumbtack so we lived in hotels in SF (crazy but true: we saved money on rent doing this). Since I moved to Exec Chairman at Thumbtack we are no longer tethered to SF so we’ve transitioned to being full digital nomads — working and living in a new place every ~month or so.

What I tried: We still work constantly but we’ve made the 🌎 our home/office instead of any one place. Puerto Rico is our home base and residency but every month or so we pick a new place to explore: the only guardrails are good weather and fast wifi. 😎 We worked at beaches (Puerto Rico, Tulum, Dominican Republic), mountains (Chamonix, Sundance), and cities (Oslo, Mexico City, NYC). We also did one month on a lake (Lake Muskoka) and one month in the bush (South Africa).

What worked (or didn’t): Making the world your office is incredibly inspiring. One of the awesome benefits of being a digital nomad is visiting places during shoulder season (example: a chalet in Chamonix in October is 80% less than during peak season). One surprising observation: It felt like time really sloooowed down since we started this experiment. 2019 felt like it was 2–3 times longer than a usual year. In the best way possible — it literally felt like Katherine and I squeezed multiple years out of 2019. I think it was the lack of routine combined with having more sunlight (we’re in New Zealand now and have 15 hours sun/day vs NYC which has 9 hours/day). There were only two challenges: 1) moving around takes lots of planning/coordination (Athena helps a lot but there’s still overhead) and 2) you have to be more proactive to see your friends (which is why we are building a traveling community).

Recommendation: This obviously requires deep minimalism and a flexible work environment, so it’s not for everyone. But it’s something we dreamed about having the freedom to do for years, and it has really lived up to our dreams. A few practical tips: A travel ergonomic setup is key. I use Apple wireless keyboard, Microsoft Arc mouse, and NextStand ergonomic laptop stand. We often stay in a normal hotel/Airbnb, but then head to the most expensive hotel in the area to work for the day. They generally have fast, free wifi and great atmosphere.

Eating without meat: Last year I tried the keto diet. This year I tried a plant-based diet. I’m not going to wade into the debate (warfare 😂) between the keto and plant-based communities (tribes 😘) but every serious nutritionist agrees that almost everyone should be eating more veggies. So I figured testing plant-based was a good push to actually do that.

What I tried: First, I read How Not to Die which details which plant-based foods have the most scientific evidence for improving health and extending life. Then I downloaded the DailyDozen app (iOS, Android) which gives you a checklist of the healthiest foods you should eat every day. I tried to check off every item on the list every day (I typically hit 20–23 out of 24 total).

What worked (or didn’t): Eating plant-based felt very healthy but I’m lucky to feel pretty good on pretty much any diet. So I tested my blood before/after to see if there were meaningful changes in my blood work. The results were amazing: in just a month of eating plant-based my total cholesterol dropped from 227 to 171 and my LDL (“bad” cholesterol) plummeted from 151 to 102 (aka from high to healthy).

Recommendation: You should eat whatever makes you feel healthy. But eating more vegetables has lots of science behind it, and eating entirely plant-based (even if only for a month-long experiment) is a great way to build a habit of eating healthier.

Drinking without alcohol: While delicious (!) alcohol is a poison. So I figured I should at least experiment with eliminating it.

What I tried: No alcohol for the entire month of January.

What worked (or didn’t): This was one of those experiments that seemed really hard in anticipation. If you live in a city, it’s pretty easy to get in the habit of drinking 5 nights/week. And the first week of the experiment was admittedly annoying (“we’ve finished work and it’s 8pm: what should we do with ourselves?”) but there was a very positive and immediate effect: Katherine and I both started sleeping better than ever and waking up with a ton of energy. I didn’t realize how much even two glasses of wine hurt my sleep. This experiment also forced us to do more of the active things we love (e.g. play tennis or trail run after work) which was an added bonus.

Recommendation: While I’m not going full no-alcohol, this one month experiment led Katherine and me to drink probably 80% less than we would have the rest of the year. I also discovered the best way to avoid alcohol: stay in environments with good weather and where it is easy to exercise a ton (trail run, tennis, lift, etc).

I’m just starting to think about what my experiments should be for 2020. Send me your ideas!

High fives and happy 2020,

Jonathan

To set some context…

A decade ago: Thumbtack had no customers, no product, no money. Our first “office” was a house, and I slept in the closet. (So, yes, I came out of the closet every morning.)

Today: Thumbtack has raised more than a quarter billion dollars, has an amazing team of nearly 1,000, and most importantly helps hundreds of thousands of small businesses earn more than $1B/year.

In between those data points were lots of 😀 and 😬 and 😱, and endless lessons learned. Below are key takeaways for current or aspiring entrepreneurs. I’ve also included some personal news at the end. Enjoy!

Lesson #1: If confidence + humility is a spectrum, you need to live on the extremes of both ends

If confidence + humility is a spectrum, you don’t want to live in the middle; you need to live on the extremes of both ends. You need so much confidence that you truly believe you can build something no one else in the world has. Confidence that you can recruit, manage, and inspire people more talented than yourself. Confidence that you can beat dozens of competitors who have bigger teams and more money. Confidence that you can persuade investors to give you the first $1M and eventually $100Ms. But just as you need ironclad confidence, you also need deep humility. Humility that your initial strategy will likely be wrong, naive, or stupid (ours was). Humility about your personal shortcomings so that you really hear and learn from your team’s feedback (the criticism will ring more loudly than the praise). Humility about your investor pitch so you learn from every investor who rejects you (there will be more rejections than investments). Finally, you need humility that the skills that made you successful during the first stage of your startup won’t be the same skills you’ll need for the second stage or third or fourth.

Takeaways: 1) Be confident that you can eventually figure everything out 2) Be humble about everything else.

Lesson #2: You must co-found a series of companies (not just one)

Scaling a startup is hard because you’re not actually building a single company. You’re really building a series of related but very different companies. At Thumbtack we’ve already built five companies: 1) the startup hunting for basic product-market-fit (1-10 team members), 2) the startup hunting for business-model-market-fit (10-40), 3) the startup hyperscaling (40-250), 4) the startup building out a leadership team (250-750), 5) the startup reinventing its business model and product (today). Thumbtack’s values and mission persisted across stages but our processes, org and team were very different. Each company is the foundation for the next, and each stage requires a new level of skillsets from the founders. As a founder, this means you must constantly be learning to scale yourself. (Jeff Jordan has a great primer on how founder skillsets should evolve through each phase.) Your goal as an entrepreneur is to build a new company and a new you at each stage.

Takeaways: 1) Treat your own leadership as a product — solicit feedback, take criticism seriously but not personally, A/B test new strategies, repeat forever 2) Hire an exec coach 3) Do 360 reviews with your team every 6 months, no matter your size. 4) Keep your identity small.

Lesson #3: Your happiness may have a .64 correlation with your startup success

The reality is: your happiness will correlate with your startups’ success. My correlation was 0.64 in these early years.

Let me share two data points to illustrate.

Raising our Series A, we pitched 42 investors…and got 42 rejections. The team was on zero salary and our bank account almost hit zero. Heartbreak, pain, agony.

Just three years later, we completed a fundraise in 72 hours that put $100M into our bank. Joy, disbelief, elation.

These sorts of highs and lows happen not just over years but often every week and even within the same day.

Takeaways: 1) Exercise consistently, prioritize sleep, and start a meditation practice. 2) Avoid what I call “projection porn” which is the root of startup whiplash. If you have a good month or week it’s tempting to project that baseline far into the future to much excitement: “If last week’s growth rate continues we’ll be making $10B/year in 3 years!” A single bad month projected far enough out can be equally soul-crushing. Resist projecting trends too far into the future; instead, focus on what you can accomplish this week. 3) When it comes to fundraising, get market feedback early and adjust. For our Series A, after 42 rejections, we re-grouped, adjusted how much we were asking for, and then we found an investor we loved who had the conviction other investors had lacked.

Lesson #4: The best companies win on product innovation AND business model innovation

We talk a lot about product innovation, for good reason. But business model innovation is sometimes even more important to your company’s success. Why? Very few companies grow virally, so most startups succeed or fail based on their ability to acquire customers. Growth hacks are effective at subscale but to reach meaningful scale most startups need to unlock paid acquisition. Paid acquisition is effectively a business model competition: the company who can pay the most for an impression, click or call wins. This is true whether you acquire customers programmatically (Google/Facebook) or via sales. That is why business model innovation is so crucial. If you can invent a new business model that monetizes better than your competitors, you will win.

Takeaways: 1) Acquisition is a business model competition 2) Early-stage founders should spend more time thinking about business model innovation and acquisition strategy.

Lesson #5: Culture is a self-fulfilling story designed to help you win

People often talk about a startup’s culture as how an office feels, or what type of people work in it or, far worse, the perks a company offers. It’s better to think of culture as a shared, self-fulfilling story purposefully designed to help you win. It is a mental picture of what your team wants to become — that you co-author with your team — and then work endlessly to turn from a story into a reality. Just as sapiens came to dominate the world by leveraging shared stories to improve group coordination (e.g. “we are Greek”), your startup should weaponize shared stories (culture/values) to help you dominate your market.

Takeaways: To purposefully design your culture I recommend these steps 1) Determine what attributes the winning company in your space will need to have. For example, the company attributes needed to win in ridesharing (e.g. speed) are very different than healthcare (e.g. rigor). 2) Determine what cultural values will produce those winning attributes (e.g. cultural value of “bias towards action” will generate speed but not rigor). 3) Relentlessly recruit and manage your team against those values.

Lesson #6: It’s helpful to have an irrational motivation

If you’re only motivated by making money or by building something cool, those drivers will be insufficient to give you the grit you need for the darkest days or the endurance you need to go the distance. The best entrepreneurs I know have a chip on their shoulder — some sort of deep, irrepressible, possibly psychologically unhealthy desire to prove themselves. I’ve purposely collected “shoulder chips” to motivate myself over the last decade, such as this email from the Stanford GSB dean about my decision to start Thumbtack (instead of going to business school). I schedule the email to re-appear in my inbox once/year. I haven’t responded to that email but I mentally relish replying one day from the floor of the NYSE. ;) It’s irrational and dumb on some level but a few irrational drivers are helpful because sometimes it doesn’t feel very rational to trudge forward when you are deep in the grind.

Take-away: 1) Having an irrational motivation is not only helpful but sometimes necessary. 2) When recruiting, look for people with chips on their shoulders. 3)If you’re climbing El Cap without ropes, see a doctor.

Lesson #7: The unsung secret of scaling is a high tolerance for boredom

People sometimes ask “is a startup a sprint or a marathon?” The best answer that I’ve heard (from my friend Ed Aten) is that it’s both: if you’ve ever watched a world class marathon runner they are literally sprinting the entire marathon. But working long and hard is obvious. The untold secret of startup life is that sometimes the biggest challenge isn’t about running fast or running out of money…but dealing with monotony. There are many thrilling and intellectually interesting moments in a startup; but there are also times where execution requires doing things that aren’t challenging or new or interesting. Example: Most people think when you raise $100M and scale your company by hundreds of people you then mainly focus on strategic, challenging problems. In fact, in times of hypergrowth, you’re often spending 25 hours/week recruiting. I literally once did 25 interviews in two days.

Takeaways: 1) The highest impact work for your startup is often not the sexiest 2) Deal with it. :)

Lesson #8: Scaling a company requires scaling yourself (hire an EA early)

Some founders take pride in working long hours. That’s dumb. You should take pride in having huge leverage (which often requires long hours). When I would work 100 hour weeks, instead of feeling self-satisfied, I knew I either 1) wasn’t delegating enough or 2) didn’t have the right leaders around me to delegate to. By working longer hours you can get 20% or even 40% more done, but with effective delegation you can get 10x or 100x more done. Eventually, as your startup matures you should delegate massive ownership of your team and product to the leaders you hire, but even from the very beginning you should be delegating constantly. I recommend every founder have a remote EA so you can start getting leverage from day one. My EA, Marni, is based in the Philippines and has helped me in endless ways: working better (pre-drafting emails, scheduling, morning bios), connecting better (organizing entrepreneur dinners, helping me invest in my network, sending gifts), living better (tracking my personal goals, planning getaways, paying bills), and so much more.

Takeaways: 1) Hire a remote EA immediately if you don’t have one. 2) If you already have an in-person EA, double your leverage by augmenting with a remote EA. You can increase your personal output significantly for $20k/year which should be an obvious decision for your startup. (Not so coincidentally, I started a company to help ambitious founders and execs with exactly this: Delegate 10x more with Athena.)

There you go. Ten years of hopes, dreams, heartbreak, and everything-in-between synthesized into a Top X list for the internet to consume. ;) I hope you enjoyed.

As for me personally, after a decade of building Thumbtack, I am excited to share that I have transitioned from President to Executive Chairman. In this role I have more geographic flexibility and will be focused on longer-term projects (e.g. recruiting new board members).

Marco, Sander, and I feel endlessly grateful for how far we’ve come in our first decade at Thumbtack, yet we regularly marvel at how much upside is still left. Thanks to the most incredible team and a massive market we have conviction there is not just 10x upside left…but 100x. We are just getting started.

Thumbtack will remain a top priority for me in the decade ahead, but I’m excited (and very fortunate) to be able to tackle some new projects as well:

• Tech investing: My investing partner Jake Zeller and I write $100k to $1M checks to founders who are scrappy, relentless and want to build massive, generational technology businesses.
• Global talent: I’m obsessed with how many talented people there are around the world and how few of those people reach their potential today. Uber and Airbnb are building $100B businesses by leveraging underutilized assets (spare cars, spare bedrooms) but the most valuable, underutilized asset in the world is people. I want to tackle this trillion+ dollar opportunity by finding new ways to leverage global talent at massive scale. As I mentioned above, the first company in this category I’m founding is sourcing high-caliber EAs in the Philippines and training ambitious founders/execs to delegate 10x more with Athena.
• Human freedom: The United States has lots of problems but remains the greatest engine for economic empowerment and human freedom, ever. Yet many billions live without basic human rights or economic opportunity. Over the next decade+, I want to do something about that. I’m inspired by how fearlessly the Oslo Freedom Forum promotes human rights in authoritarian countries, and I dream about building the ultimate startup — an entire city — to make governance more competitive and modern.
• Deep relationships: The longest study on happiness (80+ years!) had one takeaway: deep, lifelong relationships are the biggest driver of human happiness. Meanwhile, loneliness is on the rise, and is getting worse in younger generations. Silicon Valley is, understandably, getting blamed for this. But my partner Katherine and I both believe technology has the potential to help us build better and deeper relationships. We just haven’t built the right companies or—crucially—business models yet. We have some ideas for tackling this. Stay tuned.
• Traveling community: Katherine and I love investing in deep relationships as well as exploring the world, but they are typically in tension. We’d like to build a traveling community that lets us explore our pale blue dot with a close-knit, long-term community of hard-working, mission-driven people. Here’s what we’re thinking: Designing Our Dream Community.

It goes without saying, but my heart is so full of gratitude for all the support, encouragement and of course luck that helped Thumbtack get so far . This good fortune is such a gift, and Katherine and I are determined to make the most of it. Here’s to dreaming even bigger in the decade ahead.

High fives,

Jonathan

PS-THANK YOU to every person on the Thumback team, past and present, who has grinded with me early in the morning, late at night, on weekends, and everything in between. My appreciation and loyalty to you is for life. I’d also like to thank all the investors, advisors, and friends who have supported me—and Thumbtack—over the first decade, including all our angel investors (Cyan & Scott Banister, Ariel Poler, Auren Hoffman, Hadi Partovi, Josh Schachter, Jason Calacanis, Jim Lanzone, Al Hubbard, Mark Goines, Mark Britto, Denis Grosz, Tory Patterson, Naval Ravikant), Jed and Alex at Javelin, Bryan and team at Sequoia, Lee at Tiger Global, David, Gretchen, and Laela at Google Capital, our advisors (Yanda Erlich, Gary Swart, Laslzo Bock, Rich Hagberg, Laurent Valosek), and of course Marco, Sander, Jeremy, and our amazing team members across San Francisco, Salt Lake, and the Philippines. In our first decade we laid the foundation; let’s make this second decade 10x bigger!

Like last year, I’ve laid out what I tried, what worked (and didn’t), and whether I recommend trying. Check out whichever ones interest you, and let me know what you’ve been experimenting with. 😎

Delegation-by-voice: Like most people, I historically have done most my work by tapping my fingers on a keyboard. The problem with tapping fingers on a keyboard (or worse: thumbs on a phone) is: 1) it’s slow and 2) requires you to be sitting and looking at your computer. In contrast, dictation is way faster (you can talk 2–3x faster than typing) and allows you to work away from your computer.

• What I tried: My friend Denis helped me create an app for our phones that instantly starts recording upon opening. One touch to open, start talking, one touch to end, and the audio + a transcription is sent to your EA.
• What worked (and didn’t): Voice is fantastic for delegating tasks on-the-go (“Marni, pls book me a flight to Chamonix”) , writing emails (“Hey Marni, I just met with Cameron; pls send him an introduction email to Ed”), drafting letters (“Hey Marni, I need to write a recommendation letter for Ken; I’ll dictate some thoughts for the next few minutes and then pls pull together into a draft”), and even brainstorming (“Hey Marni, Katherine and I are going to brainstorm a new business idea for the next 20 minutes; pls synthesize non-idiotic ideas into an outline”). Besides being faster, voice makes it easier and more enjoyable to delegate: you can dictate while you walk between meetings, are jumping in an Uber, or strolling at sunset.
• Recommendation: This is awesome for both productivity + happiness but it takes practice. Most of us are used to only working in front of a computer or phone. It sometimes feels unnatural at first. So when my EA sends me emails I asked her to add a note to the bottom that says “remember you can dictate your response” to help me develop the habit of using voice. But the more you practice the more natural it gets. My friend Korok has been doing this for years and he has written an entire book by voice!

Daily Goal Check-ins: I started doing daily check-ins against my quarterly goals in 2017 but I’m re-sharing because this system continued to be game-changing for me in 2018. If you only try one thing from this post you should do this.

• What I tried: Every 3 months when Katherine and I have our “Life Board of Directors” meetings we set 3–4 goals we want to work on in the quarter ahead (both personal/professional). Then we have our amazing EA in the Philippines send us a daily check-in on those goals on WhatsApp. At the end of each week we get a summary of our stats for the week. (Screenshots: daily check-ins & stats summary.)
• What worked (or didn’t): This is the most successful experiment I’ve ever tried. It didn’t just help marginally; it helped me significantly with every personal and professional goal I put into the daily check-in system. Because of these daily check-ins in 2018 I exercised 226 times, meditated 182 times, read a new book every other week, stopped cracking my knuckles, and a bunch of other personal goals.The system is powerful because: (1) it is easy to record progress (<10 seconds/day) (2) the check-ins are daily and (3) there was relentless accountability (Katherine and I saw each others’ results each week).
• Recommendation: If you’d like to do this yourself (or leverage the voice delegation system above) check out Athena, a new company I’m helping get off the ground. Athena will recruit you a high-caliber EA based in the Philippines and train you to delegate 10x more.

Meditating on ideas: Last year Katherine and I started a meditation practice which we both love. But this year I also wanted to try something a bit different: meditating on ideas. There are things I know about the world intellectually but that I haven’t integrated into my moment-by-moment thinking and living. Examples: I believe free will is an illusion, our minds evolved to deceive us, and we will all die. And yet: I don’t have universal empathy for everyone I meet (you should if there’s no free will). I typically assume my chain of reasoning is–if not unbiased–at least transparent to myself (but our minds evolved to confabulate). And my gratitude for life is deep but far from unbroken minute-by-minute (but it should be if you really reflect on the brevity of life). All of these truths–if understood not just intellectually but also felt and experienced and embodied–offer the doorways to peace, understanding, empathy, and even levity. So I wanted to see how far through the doors I could go…

• What I tried: At the end of normal meditations, I would spend the last minute or so reflecting on one of these truths. If I was thinking about free will I would just imagine all the humans around me not as people but rather as tornados (since if free will doesn’t exist humans are effectively complex weather patterns). If I was thinking about death, I would imagine myself dying and reflect on how grateful I would be to have even one more day with the people I love.
• What worked (or didn’t): I’m only 1% of the way to integrating these ideas fully but even that small progress has given me glimpses of deeper gratitude, freedom, and peace. To me, these ideas feel like cheat codes for life. It’s also clear, though, that our brains are designed to reject these cheat codes. Which is why I believe wisdom is often not discovering how to live but rather habituating what we already know to be true. So this is definitely an area I want to go deeper on. I want to reprogram my mind to fully embrace these concepts so I can get their full power. I’d love recommendations from others on how to go from 1% to 2%. 🙃
• Recommendation: I certainly recommend but with a caveat: Reflecting on free will is a bit like peering over a metaphysical cliff. Some people can find it unmooring so I wouldn’t jump off the cliff if it feels too scary. For me personally, it felt uncomfortable at times at the beginning but now it only invokes a sense of freedom and peacefulness that is quite profound. I’ll leave you with my favorite quote from Seneca: “It is clear that no one can lead a happy life without the pursuit of wisdom. Yet this conviction needs to be strengthened and given deeper roots through daily reflection. You have to persevere until the will to good becomes a disposition to good.”

Eliminating news consumption: Last year one of my experiments was a deep digital cleanse. I deleted all social networks from my phone, turned off all (all!) notifications, and this year Katherine and I started a habit of never bringing phones in the bedroom. This has been amazing. But what I discovered was that eliminating those junk foods from my digital diet led me to binge on the digital crack cocaine of 2018: reading the news. I was probably checking the New York Times or Axios a half dozen times/day. 💉 So in 2018 I completely redesigned my news consumption.

• What I tried: I eliminated all news consumption (New York Times, Wall Street Journal, Axios, etc) and replaced it with more substantive sources: I listened to podcasts, read way more books, and subscribed to a few industry newsletters (e.g. Stratechery).
• What worked (or didn’t): Just attempting to not check the news on my phone didn’t work for me. My White House background + a certain US president made the digital crack too irresistible. What I had to do was literally update my browser settings on my phone to block all news sites. So if you send me a link to a NYT article on Whatsapp I would have to go to my computer to read it. 💉Extreme addiction requires extreme measures. 😂 But it worked! And what’s been most interesting is that I actually feel more informed about the world: I scan the headlines on Memeorandum a few times/week from my laptop and in just a few minutes get all the understanding I need of the drama in DC. And with all the time this frees up I’m getting way more substance from podcasts, books, and industry newsletters.
• Recommendation: Checking the political gossip on CNN doesn’t make you a better citizen. Thomas Jefferson summarizes my view: “The man who reads nothing at all is better educated than the man who reads nothing but newspapers. I do not take a single newspaper, nor read one a month, and I feel myself infinitely the happier for it.”

I’d love to hear what experiments you tried (and loved) in 2018. Happy 2019!

High fives,

Jonathan

For each experiment, I’ve laid out what I tried, what worked (and didn’t), and whether I recommend trying. Check out whichever ones interest you, and then I’d love to hear what new life experiments you’ve tried (and love!) in 2017.

Daily Goal Check-ins: In 2017 I started doing daily check-ins against my quarterly goals.

• What I tried: Every 3 months when Katherine and I have our “Life Board of Directors” meetings we set 3–4 goals we want to work on in the quarter ahead (both personal/professional). Then we have our amazing EA in the Philippines send us a daily check-in on those goals on WhatsApp. At the end of each week we get a summary of our stats for the week. (Screenshots: daily check-ins & stats summary.)
• What worked (or didn’t): Setting goals is trivial. Building new habits is hard! I’ve tried lots of ways to build new habits (competitions, prizes/punishments, etc) but the daily check-in has been the most effective by far for three reasons: (1) it was easy to record progress (<10 seconds/day) (2) the check-ins were daily and (3) there was relentless accountability (Katherine and I saw each others’ results each week).
• Recommendation: Highly recommend. I think of my ability to create new habits as raw infrastructure for anything else I want to do in life so this was definitely my most exciting experiment this year.

Meditation: I had never seriously meditated before 2017 but decided to commit to it for one year and see what I thought. I’m hooked.

• What I tried: In 2017, I meditated 296 times for more than 50 cumulative hours. For the first six months, I tried daily mindfulness meditation on the 10 minute Uber ride to work. For the second 6 months, I tried transcendental meditation for 20 minutes first thing in the morning and another 20 minutes in the afternoon. I used Insight Timer for timing the meditations.
• What worked (or didn’t): For me, transcendental meditation has been way more powerful. My exec coach gave me and Katherine a speed introduction to TM over the course of a ~week. I highly recommend having someone train you. It’s a small investment of time (only a few hours) but helps you overcome initial roadblocks, and the external accountability is helpful. I also tried a meditation retreat which really accelerates your progress. My take-away is that meditation is like exercise for your mind: it’s not going to change your life overnight, but the benefits are real and accrue with time.
• Recommendation: Highly recommend.

Exercise: I’ve always been an exercise junky but I traveled a lot in 2017 so going to the gym or on trail runs (my usual favorites) wasn’t always accessible. So I tried doing short, high intensity workouts.

• What I tried: I used the Seven app which gives you a series of 13 exercises for 30 seconds each. The standard workout is 7 minutes but I try to do 2–3 sets so the workouts are 14–21 minutes.
• What worked (or didn’t): This was awesome. These high intensity workouts made it possible for me to exercise 190 times in 2017 despite lots of travel. It’s easy to do the workout in a park or your hotel room and you basically never have an excuse not to workout for 7 minutes (or 14–21 if you have time). I was in good shape before this year but my fitness actually improved even though my total time exercising fell 50%+.
• Recommendation: Highly recommend.

Minimalism: In 2017, Katherine and I took our minimalism all the way.

• What I tried: Katherine and I eliminated everything but the clothes we could fit in a single carry-on bag, our laptops, and phones. No apartment, no car, no keys, no toilet paper. We lived in hotels and carried all our possessions with us. 1 pair of running shoes, 1 pair of regular shoes, 1 pair of pants, 1 sweatshirt, etc. That’s it. Don’t worry lots of underwear/socks/shirts. :)
• What worked (or didn’t): The simplicity has been amazing. You don’t realize the burden (both time + mental) that objects occupy in your life until you completely walk away. It was a new level of freedom. And living in hotels really simplified things; it was awesome to never make your bed, clean up dishes, or even think about buying toilet paper. And get this: living in hotels was significantly less expensive than our last apartment. (San Francisco: build some damn housing!) The biggest friction point has been laundry. Hotel laundry is crazy expensive and finding a dry cleaner is sometimes a hassle.
• Recommendation: I recommend trying if you’re in the right stage of life. Katherine and I are going to continue for all of 2018. My parent-friends like to taunt me that this won’t be possible when we have kids but I‘m living in denial for now.

Digital noise: I tested radically reducing my digital noise this year.

• What I tried: I deleted Facebook/Twitter/Instagram/Snapchat from my phone. And then I turned off all notifications for every app on the phone, except for phone calls and text messages. Katherine and I created a new rule: no phones in bed. I also attempted to read the news only a couple times/week.
• What worked (or didn’t): It took only 10 minutes to delete these apps and change notifications but the payout has been awesome. My phone now feels like a place of zen instead of a casino slot machine explosion of red dots and notifications. What was hardest by faaaaar was only checking the news a couple times a week. 2017 has made that, shall we say, rather hard. (If anyone has a good system/plugin for self-limiting certain websites like NYT/WSJ pls lmk.)
• Recommendation: Don’t even think about it. This was easily the highest ROI experiment.

Ketogenic diet: I’ve experimented with paleo, vegetarianism, pescaterian, and low carb but in the last couple months of 2017 I went more extreme and tried the ketogenic diet. Some people try keto to lose weight but I tested it because it supposedly also boosts mental clarity, energy levels, and reduces risk of cancer.

• What I tried: The keto diet is very low carb, adequate protein and high fat. Your calories should be 5–10% carbs, 20–25% protein, and 70–80% fat. If you get the ratio right, you will enter ketosis which means your body will switch from using glucose for energy to instead using ketones for energy. You can read this website or this book for details on the biological process behind ketosis and purported benefits.
• What worked (or didn’t): I’m admittedly pretty extreme about testing new things but this diet is hilariously hardcore. Reducing your carbs to 5–10% of calories requires eliminating all bread, pasta, rice, fruit (!), starchy vegetables, and more. There are carbs in so many things (breath mints!). What worked: (1) I tracked everything I ate using MyFitnessPal and (2) I measured my blood ketones frequently to track whether I was in ketosis using Precision Xtra blood monitor. With that process, after a few weeks, I found a rhythm of what I could and couldn’t eat. I haven’t noticed any differences in mental clarity (still pretty foggy up there) but the energy benefits are real. My energy is more stable than before and when you are in deep ketosis it also just feels good. What didn’t work: Meals get repetitive if you are mostly eating out (lots of eggs, avocado, cheese, burger-no-bun, etc). You have to be willing to sacrifice looots of stuff you love. For me, that was cocktails. :)
• Recommendation: I don’t recommend unless you are trying to lose weight or are masochistic, crazy life experimenter like me. What I do recommend is using MyFitnessPal to track everything you eat for a couple weeks. I learned a lot about nutrition and what foods do for me, and you can hire a nutritionist on Thumbtack to give you feedback (which I did and found helpful).

I’d love to hear what experiments you tried (and loved) in 2017. Please share.

Happy 2018!

At the beginning of 2017, Katherine Krug and I had our quarterly board meeting (if your company deserves a board meeting, why not your life?) where we discussed our favorite new habits from 2016. We also discussed and committed to our personal goals for the year ahead.

But setting New Year’s Resolutions is easy. Following through is the hard part.

So Katherine and I decided to get much more rigorous about operationalizing our goals. We decided we needed (1) relentless tracking and (2) relentless accountability.

It’s working!

Here’s what we’re doing. We use sendrecurring.com to schedule an email that gets sent to us every day at 7pm. The email includes a list of Katherine’s 4 personal goals and my 4 personal goals. The email is sent to Katherine and me, as well as our EA Marni in the Philippines.

At the end of each day, Katherine and I respond to the email with how we did against our 4 goals (e.g. yes, no, yes, no). It just take 5 seconds. But it’s very powerful because:

• We get a daily reminder of the goals we committed to (we also have a separate monthly email for goals that don’t make sense to check-in on daily)
• We have each other on the email chain so there is relentless accountability (“High five!” or “What happened today?”)
• Marni logs our answers and sends us a weekly report so we can visualize our progress over time

I’ve tried all sorts of goal setting apps but this is the first one that has really worked. It’s simple and low-tech but the relentless accountability and relentless transparency is super motivating.

High five,

Jonathan

PS-If you work at Thumbtack, we’re going to operationalize this email accountability system for any team member who wants it. We’ll allow you to set your own frequency (daily, weekly, monthly) and accountability partner (one or multiple). This is all part of bringing our mission to life: Dream it. Do it.