What determines which investor wins a competitive round: price or a pre-existing relationship?

Jake Saper · Mar 10, 2025

No competing firm or brand intimidates him on a deal; the winning strategy is getting to know founders long before the round

In Fund V they knew founders on average thirteen months before investing, and they know that lead time matters

81:01 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital

Anish Acharya · Feb 9, 2026

When a founder has a healthy, successful relationship with a past investor, you should not expect them to switch and shouldn't try to overcome it

Having been that supportive past investor himself, he wouldn't expect his own founders to go work with someone else

41:47 20VC: Is SaaS Dead in a World of AI | Do Margins Matter Anymore | Is Triple, Triple, Double, Double Dead Today? | Who Wins the Dev Market: Cursor or Claude Code | Why We Are Not in an AI Bubble with Anish Acharya @ a16z

Matt Murphy · Jul 27, 2026

Deals are won on trust and relationships rather than valuation — having someone associated with the company who can guide you in is decisive

Trust can't be established in a shotgun-wedding sprint process; the best companies are always jump balls where a long-standing relationship with a board member or associate decides it

Scope: valuation can still be painful, and for the right companies you do what it takes

44:32 20VC: Leading Anthropic's First Ever Round | Will Open Source Threaten Anthropic's Business | Do Margins Matter in a World of AI | Why Triple, Triple, Double, Double is Not Good Enough Today | Why Series A is Hard Today with Matt Murphy @ Menlo

Pat Grady · Jul 8, 2024

Delivering concrete help to a founder can create an investment opportunity where none existed

ServiceNow was generating $20M of free cash flow on $25M of ARR and had no need to raise, but after Doug connected Fred Luddy to Marty Abbott to fix their technical operations problems, Fred created a round for Sequoia — $52M for 20%

Scope: based on one deal

30:50 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

Bucky Moore · May 5, 2025

Perks and status theatrics — helicopters, courtside seats, celebrity dinners — do not actually win competitive deals

In every highly competitive process he's been in, the winner was whoever had spent close to a year developing deep insight into the founder's business, not whoever offered the flashiest treatment

Scope: about highly competitive rounds; acknowledges every firm engages in these parlor tricks and some founders respond to them

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Mati Staniszewski · Sep 8, 2025

a16z won the round by demonstrating care before investing — making valuable introductions in the weeks before any money changed hands.

They did exactly what they had said they would, introducing the team to celebrities for voice licensing a week or two before investing.

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Ophelia Brown · Mar 17, 2023

Winning the most competitive deals comes down to relentless focus and genuine, visible passion and commitment rather than process

When she wants something to happen she focuses solely on making it happen and doesn't accept no; founders can tell the passion is real

5:28 20VC: Why Growth Investors Ruined the Venture Market, Why Marketing in Venture Has No Substance, Why Follow-On Investing Can Damage Returns and The Mistakes VCs Made in the Last 18 Months with Ophelia Brown, Founder @ Blossom Capital

Pat Grady · Jul 8, 2024

Doug Leone at his peak was the best there has ever been at winning founders, and people today have not seen what made him effective

Ten or fifteen years ago he was the tip of the spear — first meeting, asking the questions, doing the work — committing fully and understanding the person and business better than anyone could in forty-five minutes, whereas recently he's been asked to parachute in as the senior big dog

Scope: refers to Doug ten to fifteen years ago

33:57 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

Jason Lemkin · Jan 4, 2024 · hedged

The best investors are 'nudges' who push their way into deals, and his own inability to nudge is his biggest mistake as an investor

The classic playbook of sitting in the lobby with a term sheet still works — Sequoia did it twenty years ago and again two months ago — whereas he only offers help and tells founders to come to him if they want him

Scope: nudging can take softer forms than lobby-sitting, e.g. dinners and persistent relationship-building

57:24 20VC: Predictions for 2024: What Happens to Early Stage VC Funding, Do a Load of Venture Funds Die, What do LPs Do in 2024, Does Figma Kill the M&A Market, Will IPOs Comeback & What Does a Trump Administration do for Startups with Jason Lemkin @ SaaStr

Max Altman · Nov 21, 2025

Investors should be more aggressive about actually offering term sheets rather than assuming proximity to a founder secures the deal

He spent weeks whiteboarding with Chris of Hadrian during COVID but never made an offer, and Delian led the round instead

Scope: lesson drawn from one missed deal

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Harry Stebbings · Jan 4, 2024

He refuses to nudge his way into deals because pressuring a founder is like forcing them into a marriage and unfairly imposing on their free will

Founders he meets experience it that way, and he believes the choice should be theirs

57:53 Refusing to pressure founders respects their free choice in fundraising

Anish Acharya · Feb 9, 2026

Winning deals is not a sales job and there are no games to play; the right move is to respect the existing relationship, state your intent to be part of every important technology story, and earn the right to lead the next round

Founders today are extremely sophisticated — you have to assume they know everything you know

42:28 State intent honestly and earn the next round

Kevin Hartz · Jul 22, 2024

Investors should not try to 'win' a deal but earn the right to work with a founder for many years; these are very different things

Overselling and BS-ing is a slick used-car-salesman mentality that dupes founders into signing rather than serving what is best for their business; he can only offer sincerity

29:36 Earning the founders trust through sincerity beats overselling to win the deal

Cem Sertoglu · Nov 20, 2024 · hedged

They lose deals mainly because other venture investors have a much lower cost of capital and can underwrite the same opportunity to a lower outcome, and sometimes because existing investors block the ownership level they want

He has to underwrite to a certain level of return, so his offer ends up not high enough against investors with lower return requirements

34:37 Lower cost of capital and blocked ownership levels explain most lost competitive rounds

Harry Stebbings · Jun 26, 2023

He wins many deals precisely because founders expect him to sit back, respond when messaged, and otherwise stay out of the way

60:02 Reputation for staying out of the way wins competitive deals

Harry Stebbings · May 5, 2025

Domain specialization does not help you pick — generation-defining founders are obvious — it helps you win, because founders choose the investor who made them smarter

Founders pick the person who made them think differently and knew the market, not the person who was merely nice

34:54 Domain expertise that makes founders smarter wins competitive rounds

Mati Staniszewski · Sep 8, 2025

Speed of execution and speed of investing is the only real edge available today, both for companies and for investors.

31:37 Speed of execution decides competitive rounds

Matt Murphy · Jul 27, 2026

The most common reason a firm loses a deal is arriving late without a pre-existing relationship

Showing up a few weeks or a month before the round against someone with a year-long relationship is a death knell

44:05 Arriving late without a relationship is why you lose