When should a founder learn a function themselves versus hire a world-class expert to own it?

Kathryn Minshew · Sep 2, 2016

Scaling was one of the most exciting parts of being a founder because it let her double down on the areas where she adds the most value and hand functional areas she was merely muddling through to people who are brilliant at them, giving those leaders latitude and authority to run their own teams

Before scaling, founders muddle through areas they aren't gifted in until they can bring someone in

12:14 20VC: How To Win The Strategic Process Of Fundraising and Optimising Co-Founder Relationships and Break Ups with Kathryn Minshew, Founder & CEO @ The Muse

Linda Lian · Apr 1, 2021

A big part of growing as a person is accepting what you're bad at and delegating it, rather than persisting at it — weaknesses don't make you less valuable.

She is genuinely bad at administrative tasks and logistics, and hiring someone who loves that work solves it better than her continued effort would.

Scope: she says she's still working out the persist-vs-delegate line

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Nick Huber · Aug 21, 2023

Gathering talented operators across many companies with extreme delegation and layering on his brand, distribution and talent-attraction is a better strategy for him than focusing on one company

He is a very good gatherer of talent rather than a deep operator, so enabling talented people and staying largely uninvolved plays to his strength

Scope: still trying to identify which business would merit single-company focus; personal to his own skill set

53:22 20VC: The Biggest Lies of Silicon Valley, Why Entrepreneurship is Not For Everyone, Why VCs are Out of Touch, Why Many Would Be Great Entrepreneurs Will Burn Out, Why You Should Let Your Children Suffer and Why You Will Choose The Wrong Partner with Nick

Craig Courtemanche · Dec 4, 2023

Leaders should know their strengths and weaknesses and hire people to cover their weaknesses

His superpowers are not in low-level operational detail, so he hires excellent people to supplement the areas where he isn't good or passionate

35:40 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

Craig Courtemanche · Dec 4, 2023

You cannot improve your weaknesses to a level that is satisfactory for the business, so you should hire specialists rather than try to become good at them

At Procore's scale a mediocre finance, HR or sales capability in the CEO doesn't help the business; his own value is in setting vision, building the annual plan, resourcing teams and being with customers

Scope: framed at the scale Procore is at today

36:22 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

Severin Hacker · May 19, 2025

Being bad at finishing the last 20% of work is not a problem for a founder as long as the founding and exec team has complementary skills, including someone obsessed with details

The final 20% is basically details, so the company needs someone who genuinely cares about details even if you don't

Scope: depends on the rest of the team compensating

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TJ Parker · Jun 5, 2023

PillPack's worst decision was waiting nine months to a year too long to bring in experienced functional operators for finance and ops

They were a deeply operational business, so the cost of leaving less experienced people to figure it out was high and the delay was incredibly painful

Scope: finding the balance between doing things that don't scale and bringing in 'adults' is one of the hardest founder judgements

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Akshay Kothari · Sep 18, 2024

When standing up a new function, don't hire the leader first — do the job yourself to learn its shape, then hire individual contributors before a leader

You need to get a feel for what the function should look like in your specific company before you can hire for it

Scope: describes Notion's approach across multiple functions

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Varun Mohan · Jun 2, 2025 · hedged

You should not make a hire until you can already get 1-10% of the outcome internally yourself

Feeling the pain first teaches you what the function actually requires and proves to the candidate that you're a company worth joining; hiring someone who isn't important on day one means they manufacture work you don't care about

Scope: still believes domain experts are valuable; framed as a personal belief and 'interesting trade off'

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Zach Lloyd · Oct 17, 2025 · hedged

Founders should try running a function themselves before hiring a leader for it, but Zach waited too long to hire functional leaders

There's value in doing it yourself first, but many people know how to do things far better than the founder does

Scope: reflecting on his own growth function at Warp

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Jason James · Aug 29, 2025

These repeat firings are caused by the founder's own muddy thinking — a founder who lacks a crisp product, culture and growth vision cannot get that clarity from a hire

Founders vaguely know they want the product to work and the business to grow, but crisp vision belongs with the founder and can't be outsourced

26:25 Vision cannot be outsourced crisp thinking must stay with founder

Kathryn Minshew · Sep 2, 2016

A core founder skill is distinguishing where you can figure out the answer yourself from where an established best practice exists and you should hire a world-class expert instead

Some domains have known best practices, so the job is identifying someone world class and giving them space, authority and resources

16:25 Distinguish figure it out domains from best practice domains

Palmer Luckey · Sep 28, 2020

A founder does not get to work on what is most technically exciting to them; if he were still doing optical design or laying out circuit boards it would mean he was being negligent in hiring

There are many people in the world better than him at those tasks, and doing them himself would be a disservice to customers, employees and investors — 'playing house' instead of doing what he is uniquely good at

31:35 Delegate even tasks youre skilled at when others

Matt Mochary · Mar 9, 2020

The right question is not whether someone is good or bad at a task but whether they love it; people are typically bad at things precisely because they hate them and so never invest the hours to improve

If you hate something you do only the bare minimum, and bare minimum never equals phenomenal — mastery takes 10,000 hours, which you won't put in on work you don't want to do

22:03 Delegate what you hate not what you are bad at