Does the founder-CEO's job get harder or easier as the company scales?

Mike Salguero · Apr 5, 2023

Running a company never gets easier, only different — the challenges don't end even after product-market fit

Once you reach the very hard milestone of product-market fit you simply inherit new challenges, and without investors telling you what to do it becomes a journey of self-discovery about what keeps you going

Scope: especially true for founders who haven't raised money

73:43 20VC: The Memo: Scaling to $600M Revenues with No Venture Funding, The Most In Detail Breakdown of Consumer Subscription Unit Economics & Why D2C and Consumer Subscription is Not a VC Backable Model with Mike Salguero, Founder @ ButcherBox

Clem Delangue · May 12, 2023

Building a company does not get easier as you scale — every stage brings its own challenges — so founders should build a company they enjoy building now rather than deferring joy to future milestones

Deriving joy from the building itself rather than from reaching a Series B, Series C or IPO completely changes the entrepreneurial journey

39:01 20VC: Why The Future of AI Is Open Not Closed, Why We Are Years Away From AI Being Autonomous, Why AI Founders Do Not Need to Move to the Valley & Why Founders Should Not Meet Investors in Between Rounds with Clem Delangue @ Hugging Face

Clem Delangue · May 12, 2023

Building a company never gets easier, and accepting that should push founders to focus on the process and on building the company they enjoy building rather than the biggest company

Realizing nothing gets easier changed his own mindset toward process over scale, and that shift proved useful and impactful

43:40 20VC: Why The Future of AI Is Open Not Closed, Why We Are Years Away From AI Being Autonomous, Why AI Founders Do Not Need to Move to the Valley & Why Founders Should Not Meet Investors in Between Rounds with Clem Delangue @ Hugging Face

Ilir Sela · Aug 4, 2023

Founders should not expect the job to get easier with each hire or milestone — it gets progressively more challenging

He repeatedly assumed the next hire or next stage would make things easier and it never did; resetting that expectation is what let him enjoy it

34:38 20VC: Why "Hire Great People and Get Out of the Way" is Total BS, Why Your Upbringing Can Make You a Worse Leader & A Bentley, Two Nissan Cubes and Becoming One of Macedonia's Largest Employers; The Story of Slice with Ilir Sela

Harry Stebbings · Dec 1, 2023

The common claim that being a founder doesn't get easier over time is wrong — it does get easier.

35:12 20VC: HelloFresh CEO on Why When You Raise VC You Only Have Two Options, Why Your IPO Price is Irrelevant, Why Timing is So Important in Going Public & Why D2C is Not Dead with Dominik Richter

Fabien Pinckaers · Feb 12, 2025

Running the company is easier now at 5,000 people than it was at 100, and being a father is not the hard part

There are no cash issues anymore — you don't sleep when you have no cash, pay salaries late and have to work twice as hard

Scope: life is still complex

63:29 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Fabien Pinckaers · Feb 12, 2025

Running the company gets easier as it matures and becomes financially sustainable

Cash pressure is what makes life unbearable — you don't sleep when you can't pay salaries

Scope: about his own experience at Odoo

64:10 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Brendan Foody · Jun 1, 2026

Running the company is easier now than at smaller scale, because supporting functions like finance and legal absorb escalations and free the CEO to focus on product, research and customers

After 7-8x headcount growth and 25-30x business growth, the functional foundations now provide stability he previously lacked

Scope: specific to Mercor's trajectory

64:25 20VC: Mercor CEO on Why Application Layer Companies Have No Defensibility, The Model is the Product | Token Spend Will Exceed Headcount Spend in 5 Years | The True Cost of Hiring AI Researchers in the Valley Today with Brendan Foody

Parker Conrad · Oct 3, 2022

The early grind of company building — convincing skeptical customers, hires and investors — genuinely gets easier over time, but the pace and volume of things coming at you gets harder

Early on nobody has heard of you so every first customer and hire is a fight; later the firehose you're drinking from keeps getting bigger and coping with it is the hard part

25:31 20VC: Rippling's Parker Conrad on The Four Main Benefits From Building a Compound Startup | Why There Should Never Be a Trade-Off Between Speed and Quality | How Zenefits Gave Parker a Chip on the Shoulder and Why That is so Important?

Ilir Sela · Aug 4, 2023

Scaling makes the job harder even as it gets nicer, because the stakes and the number of people you can let down keep growing

One release can disappoint a huge number of customers, and investors and mission-driven team members are all people he doesn't want to fail; as that denominator scales, the pressure to limit mistakes grows

Scope: 'at least that's my approach'; concedes it is 'nicer' with more team support

35:11 20VC: Why "Hire Great People and Get Out of the Way" is Total BS, Why Your Upbringing Can Make You a Worse Leader & A Bentley, Two Nissan Cubes and Becoming One of Macedonia's Largest Employers; The Story of Slice with Ilir Sela

Craig Courtemanche · Dec 4, 2023

Being CEO doesn't get easier over time, it gets different — the baseline level of stress has not diminished at all

With 4,000 employees and 16,000+ customers the blast radius of a screw-up is so large that it can't be taken lightly

Scope: acknowledges that security and stability from success are priceless

38:07 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

Eléonore Crespo · May 9, 2025

As a company scales the founder's job gets easier in some ways and harder in others: delegation to empowered hires relieves the founder, but rising organisational complexity means every decision carries far bigger consequences

Hiring people who scale with you removes the need to do everything yourself, but with a larger team each decision now has a big impact

Scope: both effects hold simultaneously

50:57 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Harry Stebbings · Jun 26, 2023

The mantra that 'it doesn't get easier' is false — it does get easier

His own experience: he now gets San Pellegrino delivered and records in a nice studio in Belgravia

23:34 Personal life and work genuinely get easier with success contrary to the mantra

Harry Stebbings · Dec 4, 2023

Reaching success does make the CEO job easier in one respect — the absence of existential financial fear removes a real form of pressure

He contrasts early-stage terror of ending up on the street with now having a beautiful house and stability, even though pressure remains high

38:09 Removal of existential financial fear genuinely eases the ceo role even as stakes rise