How should a founder-CEO decide what their own job should be as the company scales?

Delian Asparouhov · Jul 29, 2024

He chose not to be founder-CEO of Varda because you should occupy only the role where you can be in the top 0.1% — he is unsure he could be a top 0.1% CEO but is convinced his cofounder can, while he can be top 0.1% as president/chairman

Comparative conviction about who can be in the top 0.1% at the CEO job should determine who takes it

Scope: allows that over the next decade or two, with more experience and emotional maturity, he could do the CEO job

72:16 20VC: Twitter's Most Controversial VC Delian Asparouhov on Inside the Walls of Founders Fund: What the World Does Not See | Why Western Europe Will Be Like the Third World | Why SaaS as an Industry Might Be Dead

Guillaume Moubeche · Dec 13, 2024

A founder should move to chairman and hand the CEO role to someone else when that person is genuinely better at day-to-day operations, while the founder concentrates on the top of the funnel

He is best at conferences, content, webinars and attracting audiences, while a CEO needs to be in the trenches operating daily; the person he hired 18 months ago is definitively better at that

Scope: specific to his own skill profile; presupposes an already-proven internal hire

40:00 20Growth: How to Scale to $30M ARR Bootstrapped through Content and Brand | The Ultimate Equation to Success in Sales and Why Most Founders Suck at Sales | Why You Should Overpay People and What That Means with Guillaume Moubeche @ Lempire

Alex Bouaziz · Oct 22, 2025

He wants to keep running Deel whether public or private, conditional on being the best person for the job

The right criterion is who can best run the business, not the company's public/private status

Scope: conditional on remaining the best person to run it

59:39 20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Adam Foroughi · Apr 27, 2026

In any role, including CEO-as-chairman, if there is someone better suited you should step aside and let them take it over.

His job is to run the business day to day, not consume his time on governance; handing the chair to someone exceptionally talented at corporate governance is a good trade and keeps the whole team leveling up.

Scope: he notes it is uncommon for CEOs to step aside as chairman; he says he has limited experience with boards

69:35 20VC: Applovin: $160BN Market Cap, $5.48BN Revenue, $10M EBITDA Per Head | Why the Best Do Not Need Mentorship | Why Founders Should Not Angel Invest | Why Kindness in Business Will Slow You Down with Adam Foroughi

Ryan Petersen · Nov 13, 2023

In public companies, the CEOs with the best long-run stock returns are excellent resource allocators — they know when their stock is over- or undervalued and buy back or issue and acquire accordingly

Buying undervalued own stock and issuing overvalued stock to acquire other companies is the purest form of resource allocation available to a public company

Scope: public companies; over a long horizon, e.g. fifty years

10:58 20VC: Flexport's Ryan Petersen: Reflections on Leadership from 13 Years Leading Flexport, Why Velocity not Speed is Most Important in Company Building, How Money Creates Inefficiencies in Scaling, The Future of Trade with China & Why Remote Work is so Cha

Craig Courtemanche · Dec 4, 2023

Being an efficient capital allocator is one of the top four jobs of a CEO

Reading The Outsiders was cathartic in showing him this is the core of the job, and as the responsible party he has to get it right

49:33 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Sanjit Biswas · Dec 8, 2023

The CEO is the chief capital allocator of the company, which in a software company means deciding where people's time goes

For a software company most money is spent on salaries, so allocating people time is allocating capital, and somebody has to be the editor in chief on that call

Scope: framed for software companies specifically

31:45 20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara

Sanjit Biswas · Dec 8, 2023

Being CEO only started to feel natural several years in, around 100 people at Meraki, when he accepted that the job is leading the whole business rather than being the engineer or chief salesperson

Realising his salary was booked under G&A rather than R&D crystallised that leadership — capital allocation and being the soul of the company — is itself the job

40:32 20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara

Harry Stebbings · May 8, 2024

Outcome scenario planning that caps a company at $1-2B is facile thinking, because the difference between a $2B and a $10B business is a great founder and exec team

Execution quality by the founder and executive team, not the initially-assessed market, determines whether a company reaches $10B

36:56 20VC: GV's Tom Hulme on Why Investing in Foundation Models is like Investing in "Power Stations", The Conventional Wisdom in VC that is BS & Lessons from a 24x Angel Track Record, 255x on Robinhood and Making Billions on Uber

Harry Stebbings · May 8, 2024

A truly great founder and team will have a second act if the first insertion point is too small — parlaying it into a product suite or platform play and capitalizing a $1-2B business into a $10B one

Great founders don't stop at the initial insertion point; they extend into new products and platforms

Scope: applies only to 'truly great' founders and teams

37:30 20VC: GV's Tom Hulme on Why Investing in Foundation Models is like Investing in "Power Stations", The Conventional Wisdom in VC that is BS & Lessons from a 24x Angel Track Record, 255x on Robinhood and Making Billions on Uber

Harry Stebbings · Jul 8, 2024

The difference between a $1 billion company and a $10 billion company is a truly exceptional founder.

Exceptional founders find the second product.

16:45 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

Harry Stebbings · Sep 11, 2024

The difference between a billion-dollar company and a ten-billion-dollar company is a founder able to transition between chapters — a $10B company requires a second or third act

41:21 20VC: Scaling ServiceNow to $5BN in ARR | Leadership Lessons from Doug Leone, Frank Slootman and Bill McDermott | VC Value Add: Is it Real and Why the Worst VCs are "Seagull VCs"

Mike Shebat · Nov 27, 2023

As a company scales, a founder must concentrate their finite hours on the few highest-leverage activities that could 10x the business rather than treating every detail as equally important

There are only a finite number of hours and a finite amount of energy in a day, so equal weighting of details wastes the founder's leverage; the rest should be delegated while still being pressure-tested

Scope: details still matter; delegated work should still be pressure tested

39:27 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Victor Riparbelli · Jan 15, 2025

Existing lines of business can be delegated to smart hires, but pushing to the next product market fit and defining where the company needs to be in two or three years remains the founder's job

10:51 20VC: Why Scaling Laws Will Not Continue | OpenAI vs Anthropic vs X.ai: Who Wins and Why | How Far Will Model Providers Go Into the Application Layer | The End State for Models: Many Specialised or Few Generalised with Victor Riparbelli @ Synthesia

Johannes Reck · Jun 23, 2025

A CEO should treat themselves as a system and structure their time around the one or two things they are uniquely qualified to do better than anyone else in the organization

His own spike is strategy and intuition, so he deliberately reserves time to brainstorm, review metrics and refine strategy rather than filling his day

Scope: especially true for founder CEOs with historical context

66:32 20VC: The Wild Story Raising $450M From Masa and Softbank | Why My Biggest Mistakes Came From Listening to VCs | Why 100 VCs Turned Us Down | Why European Founders Are Tougher Than US Founders with Johannes Reck, GetYourGuide

Sanjit Biswas · Dec 8, 2023

Founders should periodically 'rehire themselves' by writing the job description the company needs for the next year or two and checking whether how they spend their time matches it

It forces you to test whether your current activities match what the organization actually needs from you

7:11 20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara

Andrew Dudum · Apr 4, 2026

If you can't hire people smarter than you, you will fail; a leader should aim to replace themselves every twelve months with talent equal or better

Your job changes every twelve months as the organization scales, so you have to level yourself up to the next highest-leverage focus area; young managers avoid this out of fear of being made redundant

9:19 20VC: Hims & Hers: $4.3BN Market Cap on $2.3BN of Revenue: The Comeback | Why Being Public is 10x Better | The Death of the "Strategy" Hire | Why Performance Marketing is Worse than Brand Marketing with Andrew Dudum

Jeff Lawson · Jun 28, 2021

In a fast-growing company a CEO has to reinvent how they lead roughly every twelve to eighteen months, or risk falling behind the needs of the company

The organization becomes bigger, more diverse and holds more viewpoints, so the mechanisms used to lead must continually evolve

Scope: give or take, generally speaking; in a rapidly growing environment

13:36 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better

Miki Kuusi · Nov 28, 2022

Being CEO of a fast-scaling company means repeatedly feeling underwater and having no idea what you are doing, because the role keeps changing beneath you

He went from idea to 7,000 people, and at each stage faced problems he had never encountered — hiring a first recruiter, building a growth-round deck — with no prior knowledge, and had to pick them apart under time pressure

33:36 20VC: Wolt CEO, Miki Kuusi on Leadership Lessons Scaling to a Reported $8.1BN Exit to Doordash, Building Teams not Families, The Difference Between Trust and Safety Within Companies, How To Use Compensation to Create Culture & Why You Should Not Be Lookin

Geoff Charles · Dec 6, 2023 · hedged

The CEO role is mostly storytelling, press and investor work, which would leave a builder-operator stretched and unhappy — so he doesn't want to be one

He has little patience for fundraising and isn't a strong marketer; he shines at building great products

Scope: maybe if he found people to compensate for those gaps

49:32 20VC: Ramp's Product Playbook: How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go Multi-Product with Geoff Charles, VP Product @ Ramp

Adam Foroughi · Apr 27, 2026

Once a company is playing at higher-stakes tables, being publicly visible and explaining the business model is a key part of the CEO role, and leaders should push themselves into uncomfortable formats like public speaking.

People need to understand what the company does to understand the business model and its prospects, and challenging yourself at things that are naturally uncomfortable is rewarding.

Scope: applies as the company gets bigger

40:33 20VC: Applovin: $160BN Market Cap, $5.48BN Revenue, $10M EBITDA Per Head | Why the Best Do Not Need Mentorship | Why Founders Should Not Angel Invest | Why Kindness in Business Will Slow You Down with Adam Foroughi

Craig Courtemanche · Dec 4, 2023

The hardest and most important leadership transition is learning to stop doing the work yourself and start leading, and it is one of the biggest challenges anyone faces

In early-stage companies your job is literally to do everything, so letting go and empowering people is an unnatural motion; he still sees new managers at Procore struggle with it

Scope: applies to new managers as much as founders

33:44 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Max Junestrand · Aug 15, 2025

The hardest founder transition is from individual contributor to manager, because the school-project instinct to just do the work yourself is wrong in a company

A group project lasts two months so doing it yourself is efficient, but a company lasts years or decades, so doing the work yourself saves fifteen minutes while failing to grow the team

67:09 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Alex Bouaziz · Oct 22, 2025

A CEO's job is to enable — to find what's broken for each leader and unblock it with resources, prioritization or reorgs

Being hands-on in the problems his reports face every day is what lets him do that enabling work

17:10 Ceo job is to enable by unblocking leaders

Zach Perret · Oct 16, 2024

The best long-tenured public-company CEOs are the best resource allocators, but at earlier stages the CEO's highest-value work is finding product market fit and then building an effective company

What matters depends on the horizon and scale of the business

8:29 Long tenured ceos are resource allocators but early stage job is pmf and org building

Alan Chang · Jan 5, 2026

Being CEO is worse than being a senior leader in one respect: you no longer get to choose which problems you work on, because you hand those opportunities to other leaders

At Revolut he could pick the role and problems he wanted; as CEO he gives that choice to his leaders, so by definition he can't choose — he'd rather be going deep on low-level hardware engineering

51:13 Ceo gives up choosing which problems to work on

Dominik Richter · Dec 1, 2023

Calling the best CEOs the best capital allocators is too narrow a financial framing; resource allocation — deploying and organising people to bring out their best — matters equally.

It's the view a PE fund would give; the CEO job includes where people are placed and how they are organised, which is as important as capital allocation.

16:40 Resource and people allocation matters as much as capital allocation

Anastasios Angelopoulos · Aug 3, 2026

Managing people is the most important part of running a company, and strategy and forecasting matter more than technical skill

He spent his PhD proving theorems, but running a company is about people, strategy and being able to see six months to two years ahead and plan for it

54:41 People management and forward planning over technical skill

Fabien Pinckaers · Feb 12, 2025

The founder's job changes qualitatively by stage: 1–10 is building the business and product, 10–100 is communicating culture because middle managers now carry it, and beyond 1,000 it is all about scalability

Above 10 people the culture is no longer you but the middle managers and how they behave with people, so alignment communication dominates

35:09 Founder job shifts by stage building then culture communication then scalability

Paul Erlanger · Jun 27, 2026

The founder and CEO's main job is sales — selling to future employees and selling the product and vision

23:00 Ceo job is selling vision to recruits and users

Tom Hulme · May 8, 2024

Team quality alone does not get a company from $2B to $10B: the market opportunity must persist for a long time, competitive threats must stay out, and the market must be big enough — and those three conditions are often absent

Building a $10B business usually takes a long time, so the market opportunity has to persist over that period

37:13 Market persistence and absence of competition also required not team alone

Tom Hulme · May 8, 2024

There is real option value in a brilliant, well-resourced team parlaying a $1-2B business into something larger, but under 1% of companies ever reach that starting point

A team that has already reached $1-2B has the resources to attempt a second act, but the base rate of getting there at all is extremely low

37:47 Option value exists but under one percent of companies reach the threshold

Christa Quarles · Jul 29, 2021

The three decisions only a CEO can make are the brand, mission and narrative of the company; putting the executive team in place; and owning the interface with the board.

No one else can craft the company's purpose or long-term narrative, only the CEO can assemble the team that makes the company successful, and the board relationship is the CEO's own fiduciary duty.

29:27 Three things only ceo can do brand narrative exec team board interface

Scott Farquhar · Oct 9, 2023

A CEO's job is four things: hiring/firing the management team, setting the vision, setting the culture, and resource allocation

These four are the most important levers, and he audits his calendar against them to check where his time goes

18:52 Ceo job is four things hiring firing vision culture and resource allocation