A portfolio founder approaching $100M in ARR asked me about the single biggest and most impactful hire they can make.
I thought for a bit tand said: "Hire a near-peer".
In every generational company I've been part of, the founders hired a near-peer, who was essential to the company's success.
- Google: Larry and Sergey hired @ericschmidt .
- Facebook: Mark hired @sherylsandberg .
- Square: Jack hired @rabois .
- DoorDash: Tony hired @chrispa
- Coinbase: Brian hired @emiliemc
Characteristics of a near-peer: 1. They're so good that the founder will be fine reporting to them if the roles were reversed. (Mark has said publicly that he'd be fine reporting to Sheryl) 2. Their strengths perfectly complement the founder's strengths; however, they share many cultural attributes with the founder and pass the founder's airport test, since the founder will be spending a ton of time with them (example: Eric being a Computer Scientist, which was culturally very important at Google back in the day) 3. They're systems builders who have already operated at the scale you're growing into. Pattern recognition on $100M to $1B is not something you build in real-time.
A near-peer lets the founder focus on what only the founder can do (product, vision, culture). The near-peer handles everything else.
Also, near-peers stay for the long haul. Decade-plus tenure is standard.
The reason this hire matters more than any other: after $50M ARR, the bottleneck shifts from product-market fit to organizational scale. The founder is still the visionary. But the company needs someone who has already scaled a company of that size.
Most founders wait too long. They hire functional VPs first (Sales, Marketing, Engineering, Finance) and hope the collective covers the gap. It rarely does. A stack of VPs reporting into a founder who has never scaled a company creates coordination overhead, and the founder becomes the bottleneck.
The near-peer absorbs that overhead. They turn the founder's vision into daily operating decisions. They give the VPs a leader who has actually run a company this size.
Growth founders: if you're between $50M and $300M in ARR and every week feels like a coordination tax, the near-peer is the hire that determines whether you build a $10-100B company or top out at $1B. Start the search now, ideally through warm intros from your venture/angel investors and advisors.
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I didn’t overlap with @keithrabois at @Square, but when I joined, his precepts were (and still are) all over the company. One of the most powerful metaphors - not least because of the vivid imagery - was that of barrels and ammunition.
2. I use this metaphor often with founders. We were fortunate that Keith hired a number of barrels at Square. Not surprising that barrels make great entrepreneurs - many of these people have started category-defining companies.
1. One of the maxims about a startup is “everyone wears all hats”. This is not true about founder roles. With very few exceptions, it’s extremely important to clearly delineate founder roles between a BUiLDER and a SELLER. (Or more colloquially, a hacker and a hustler).
2. The builder role owns building the product, end to end. The seller role owns figuring out how to get distribution for the predict, but also interfacing with external constituents such as investors and partners.
3. Note that i didn’t say “skills”. I said “roles”. When two trained engineers are cofounders, one assumes the Builder role and the other takes on the Seller role.
With three cofounders, at least one must assume the Seller role.
0. Founders/CEOs: what are your thoughts on employee transparency? how transparent should founders be with employees? And on what topics?
DISCLAIMER this question is for startups and private cos only. Public CoS have a much higher level of requirements around confidentiality.
1. Context: A founder confided that a good chunk of their engineers quit because the founder was too transparent about the company’s fundraising struggles last year (co did ultimately raise strong round). He agonized over whether this was preventable, whether he had over shared.
2. My take: founders should be transparent about things that directly impact employees’ work, things that are in the here and now, and things that are irrefutably true and verifiable.
1. Founders and CEOs don’t have a good way to think about competitors. Some ignore them, others obsess over them. Neither is optimal.
IMO, the right way to evaluate competitors is through a customer lens.
2. Specifically, being obsessed with your customers’ problems will help you see early if a competitor is solving their problems better than you are.
The bigget thing that matters wrt competition is if your customers are choosing or switching to a competitor over you.
3. And if you see this happening, you need to root cause it with extreme urgency, figure out why your solution is falling short of your customer needs, and fix it.
1. If you work in tech, especially in Silicon Valley, check out @arta_finance - they just launched a new way to manage your finances with advanced tech like AI & ML. It’s designed to address the financial questions & challenges that so many of us in the tech industry have.
2. How do I manage my equity, make it work for me, get liquidity without selling, optimize for taxes, and determine if and when financing is worth it?
3. What’s the best way to build long-term wealth with my resources? How do I think through the tax implications of grants or vests or sales? How should I think about my RSUs? The list goes on.
1. There will be a spate of acquihires in the next 18-24 months. I've been closely involved in a dozen plus acquihires. After seeing both successes and failures, I believe he 3 principles of a successful acquihire are:
(a) Talent
(b) Domain
(c) Team size
2. Talent: Since acquihires are about talent, there must be 1-2 verifiably (ideally through prior collaboration) exceptional people on an acquihired team, folks who raise the bar for that function or domain at the acquirer. Acquihiring an average team is not worth the trouble.
3. Domain: The acquihired team should work in the same (or adjacent) domain as the acquirer. Otherwise, the acquirer ends up with a team that went along with the process for lack of options, but leave after 6-12 months because they are not excited about the space or mission.