Hi there, and welcome to my newsletter — about all things future of work, company-building, and operating.
I’ve been building companies for 15 years, starting with Thumbtack (local services) and now Scaled (startup recruiting) and GroomBuggy (dog grooming). I’m motivated to get jobs for people as tech accelerates. This newsletter chronicles my birds-eye view on the workforce and my journey in creating jobs for the future.
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🔭 Explore
The world is your playground.
Opportunity for many is near limitless.
Explore your passions? Do that.
Follow your curiosity? Do that.
Learn from the smartest people? Do that.
The best lives are played like a video game. Grand Theft Life.
Play. Dabble. Watch. Prototype. Hang out. Read. Enjoy. Explore.
Exploring is fun. It’s also critical for success.
Turns out — the 10,000 hours rule is mostly wrong.
Having more diverse experiences across multiple fields is more relevant in today’s society than specialization because the problems of the modern world require bridging experience and knowledge from multiple fields to foster solutions.
The most successful people in their fields are much less like Tiger Woods and much more like Roger Federer.
Tiger Woods played only golf starting at 4 years old.
Roger Federer explored many sports and focused on tennis only when he reached his late teens.
It’s almost always the Rogers who reach the peaks of their professions and not the Tigers.
Musicians should learn all instruments before specializing.
Parents should expose kids broadly not focus them narrowly.
Students should study across domains not just one.
You should follow your curiosities regardless of whether doing so brings you value today.
Experience is not a good predictor of skill in a wide range of areas. Over-reliance on past patterns can backfire badly. The most successful experts participate in the wider world. Creative achievers have broad interests. Outside-in thinkers solve problems that stump specialists.
Flirt with many possible selves. Escape your local maximum. Don’t marry one identity. Keep options open. Roam freely. Consume omnivorously.
Explore.
⛏ Exploit
There were entire years at Thumbtack where I read no news. Where I took virtually no outside meetings. Where my health suffered and my friendships decayed. Where I was consumed by one obsession: making the company work.
All else I put aside.
It was narrow, focused, non-exploratory.
And these were some of the happiest times of my life.
The most meaningful things in my life have come from moving from exploring to committing.
Exploring for a year on weekly phone calls with Marco and Jonathan ideas of things we could start to create economic opportunity for people, and committing to Thumbtack.
Dating, then marrying.
Knowing nothing about digital marketing, then becoming the best at SEO.
Knowing nothing about SEO, then going all in on link-building.
Not having kids, then having kids.
There is nothing more fulfilling than committing to one thing with likeminded comrades and locking arms to face down the enemy and past demons and willing your vision into existence with months or years of brutally hard work and tears and setbacks.
The things we are most proud of are the things we commit to for the longest time, at great opportunity cost, often unreasonably and irrationally.
In a world of super-abundance, why commit? why be loyal? why limit your options?
Because that’s where the best of life is found.
☯️ True masters
The most successful people follow cycles of exploring and exploiting.
For a period they explore their curiosities, re-learn the state of the art, reengage with the community of knowledge.
Then they exploit. They identify their new teammates. They restrict the option set. They focus and execute for months or years until they reach their next local maximum.
The cycle repeats.
Give it enough cycles, and for good people this pattern will pay off.
Repeat founders follow this cycle.
The most interesting careers follow this cycle.
The greatest inventors follow this cycle.
With each new cycle you’ve gained a new expertise, a new community of people, a new aperture from which to view the world, a new shot on goal.
You stand atop compounding gains.
True masters parallelize the two instead of serializing them, allocating most of their time to exploiting and some of their time to exploring. So that they can shift rapidly to a new exploit once the current one reaches diminishing returns.
True masters have systematized this. Elon Musk piggybacks new companies off of ones he’s already started. Mike Speiser does this at Sutter Hill Ventures. Barry Diller did this at IAC.
At Thumbtack we created Thumbtack Labs so 80% of the team could execute without distraction and 20% of the team could ideate without distraction.
Among my friends who have had some success as first-time founders, the model they’re most attracted to the second time around is a venture studio or conglomerate or long term holding company or loose federation of closely-held companies and trusted people who are systematically exploring together and then ready to converge on and scale a winner the moment they see it.
Over the last year or two I moved from 90% time at Thumbtack to 90% time exploring. Exploring recruiting. Angel investing. Acquiring small businesses. Attending conferences. Dog grooming. Metabolic health. Venture studios. Crypto rabbit hole.
I’m re-focusing again. I’ve found a winner and I’m ready to exploit.
One can explore too much, and one can exploit too much.
Symptoms of over-exploration: aimlessness, lack of commitment to anything, dissatisfaction, wishing you were part of a team, sad that you’re not passionate about something, boredom.
Symptoms of over-exploitation: you haven’t made step change progress in a while, you can do your job on auto-pilot, you feel stuck in your career, you feel locked into your lifestyle and income level.
Exploring or exploiting — where are you?
🎨 Business updates
🐶 GroomBuggy
GroomBuggy will have the best digital marketing of any mobile dog grooming company on the planet. This month I got back to my digital marketing roots and did a deep dive on Google My Business listings. If you or someone you know has experience setting up Google My Business listings at scale for companies with numerous local locations — I would love to chat.
Our motivation in building this company is to make dogs (and their owners) happy and to create great jobs for our groomers. It is so much fun.
🧗🏼♀️ Scaled
Nothing is more important in scaling a company than hiring great talent. There aren’t enough good recruiters given the importance of the function. At Scaled we help founders and team leaders hire great people quickly. Our core product is helping startups hire great People, Finance, and Legal talent. We are also beta testing a new product to help startups hire other roles. The team is fun because they are very good and the cost of our service is reasonable. Let me know if you or someone you know is interested in help recruiting or lowering recruiting costs.
📌 Thumbtack
Last night Marco and I celebrated Thumbtack’s 14th anniversary with fancy sushi. Yum. 🍣
🎒 Grab bag
📖 Book of the month. There is someone named Frank Slootman who has largely been ignored but is one of the great CEOs of our generation. He almost-single-handedly transformed three companies into behemoths. He’s currently the CEO of Snowflake, a $50 billion company. Earlier this year he published a book called Amp It Up about his management philosophy. His style is not mine but I love it. He is a true operator and a real hard ass. He tried to be a VC and failed. His lessons are borne of hard won experience. He prizes great execution above all. He believes there’s a huge dearth of execution talent in tech and beyond, that great operator-managers are the most valuable people around, and that slow execution and poor management is endemic to tech startups — these companies can get away with poor execution due to monopoly returns of software. I think he is ignored because he speaks uncomfortable truths. Reading the book gave me so many ideas of how I can raise my game.
✊🏻 Movement of the month. In a former life I was a lawyer and thought I was going to live in D.C. doing political work my whole career. At Thumbtack I led or was involved in our public policy work for years. I still love politics and in particular am passionate about ensuring that the next generation of people across America can get good jobs to support themselves and their families. I’m inspired by — and in some cases have become a part of — a handful of newer organizations or movements that support an “abundance agenda,” including Effective Government California, GrowSF, Dialogue, Merit America, YIMBY Action, a16z’s Katherine Boyle, Derek Thompson’s Progress and Ezra Klein’s work. This is a bipartisan group of folks who believe that maintaining vibrancy in our economy depends on focusing on outcomes not process, on minimizing protectionism, corporate welfare, monopolies, licensing organizations, local zoning regulations and other forms of concentrated interests. Let me know if you’re interested in connecting with any of these organizations or know of others doing good work here I should meet — I want to get more involved.
🦍 Self-promo of the month. Yours truly did a podcast with one of my favorite people + companies — Sam Corcos at Levels — about how to scale teams beyond 50 people. Take a listen if you’re curious about how we tackled team growth at Thumbtack during that period.
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See you next month!
👋 Sander
Sander's Newsletter, Issue 5
Explore v Exploit. I love the shifting between them and knowing how & when to reallocate your time. Too many people get off balance in exploit mode and forget to direct some of their time and energy towards exploring. There may be times when you don't do any exploration, but in my view they should be short sprints.