SWLW #619: A Startup Founder to Scaleup CEO’s Journey, "Owner Mode" beats "Founder Mode", and more.

A weekly newsletter by Oren Ellenbogen with the best content I found around people, culture and leadership in tech. You can also read this issue online and recommend this newsletter to your teammates for a great discussion.

Like always, sharing my best findings for the week.  

 

This Week's Favorite


A Startup Founder to Scaleup CEO’s Journey From $0 to $25billion (Halliganism’s)
12 minutes read.

Brian Halligan shares his journey of over 15 years as HubSpot's CEO, starting from a tiny startup to a successful public company. One insight that took me a decade to learn is how to optimize decision making, or as Brian puts it: "EV>TV>MeV: It is critical that everyone in the organization solve for the Enterprise Value over their Team's Value and over Their Own Value (MeV) when they are making decisions."

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Culture


The Season 7 of Silicon Valley
1 minute read.

My humble effort to help you start the weekend with a smile on your face. There is a probability of 97% of it happening both in the TV show and in real life.

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To Scale to $100M ARR, “Owner Mode” Beats “Founder Mode”
9 minutes read.

This is an insightful post managers must read. The section under "Where I land: Six principles for founder-CEOs" at the end should be reviewed and benchmarked against. Keeper test, meetings overflow, management layers, OKRs trap. So many gems.

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10 Companies That Hit Massive Scale With Surprisingly Small Teams (Thread)
4 minutes read.

You can get inspired by these companies, staying lean yet creating tremendous impact. Hiring more people shouldn't be your first (or only) solution to increase your capacity.

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Founder Mode: A Sign You Have Yet To, or Failed To, Hire the Right People and Build the Right Culture.
4 minutes read.

Amir Shevat covers what feels like a misalignment between the people we hired, their (intrinsic) motivation, and the company's needs: "The essence of founder mode, or diving deep, is a fantastic concept. I see successful founders use it all the time. They find places where things aren’t working, deep-dive into them, fix them, make sure they’re staffed with the right people, and move on. [...] Talented people understand that leadership sometimes needs to be in founder mode, but if it persists for too long, they feel strangled and leave [...] So, don’t take the cop-out route and the ego trip that comes with “I can do it all.” Instead, do the hard thing — hire amazing, driven people and build a culture that outlasts you."

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Peopleware


When to Do What You Love
5 minutes read.

"What do you do in the face of uncertainty? Get more certainty. And probably the best way to do that is to try working on things you're interested in. That will get you more information about how interested you are in them, how good you are at them, and how much scope they offer for ambition. [...] One useful trick for judging different kinds of work is to look at who your colleagues will be. You'll become like whoever you work with. Do you want to become like these people?" -- For many of us, it takes decades (if not a lifetime) to figure out what we truly want to do. For all of us, who we surround ourselves means everything to us. Iteration is one way to learn that, but make sure your environment sounds as appealing as the work you'll do.

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Ask HN: As a Manager, How to Increase the Sense of Urgency of the Team? (Thread)
5 minutes read.

Interesting comments and ideas for creating urgency in the team. For me, urgency can be done by external factors (deadlines due to customers' commitments) that lose their effectiveness if it happens more than 3-4 per year. A better approach is to hire someone who wants to prove a point (intrinsic motivation), give them a clear goal that aligns with the company's needs and their needs, and then iterate with them on what else they want to prove once they get there.

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Bureaucrat Mode
5 minutes read.

"We can read the above list and laugh (and cry a little too) but of course they fundamentally are the result of good intentions. After all, we’re forming committees to facilitate communication when very complex initiatives like products are getting launched. There’s just a lot of details, and a lot of tradeoffs, and not everyone agrees. This is the good interpretation of this." -- Given that we've all seen people adopt and work for the process (instead of it serving them), there needs to be a counterforce that constantly challenges core assumptions and methodologies and gets the authority to act to simplify the organization and the processes. Alignment is critical, consensus is not. Shared context is critical, equal experience is not.

Read it later via Pocket or Instapaper.
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And finally, inspiring tweets...


@lateinteraction: “Complexity is actually a necessary ingredient to progress, but it's not where we stop. We're not done by the time we've solved it — we're done by the time we've made it simple.”

@nukemberg: There's more to making senior engineers than teaching or mentoring. Giving personal example for example, developing good protocols and guardrails another.



p.s. if you're interested in joining SWLW's Slack channel, simply reply to this email and let me know. If you're leading a team, consider writing your Manager README (it's free) or getting my e-book and interviews Leading Snowflakes: The New Engineering Manager's Handbook. You can also support me by becoming a SWLW Patron. Thank you ❤️




Keep reading, keep learning.
-- Oren Ellenbogen.

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