How long a time horizon should founders operate on when making decisions?

Kulveer Taggar · May 31, 2019

Founders who think on a long (10–20 year) time horizon make better decisions and gain an advantage over those operating on short horizons

His Auctomatic team was impatient and sold within a year; he believes a longer horizon would have produced a better outcome

6:19 20VC: Why You Must Have A Customer Acquisition Strategy From Day 1, How To Test and Validate Ideas At Speed & Why You Should Speak To Investors Before Starting Work On Your Idea with Kulveer Taggar, Founder @ CEO @ Zeus Living

Sanjit Biswas · Dec 8, 2023

If you intend to scale 10x repeatedly you must allocate capital for the long term, including R&D budget for products shipping one to three and three-plus years out

At Meraki they were just trying to hit the next revenue milestone and survive, so they didn't build for the long term; at Samsara they assumed repeated 10x scaling from the start

Scope: contrast drawn against a capital-constrained post-GFC environment

32:08 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

Building for the long term rather than a year at a time is the underappreciated key advantage, and most first-time startups don't do it initially — they're just trying to stay alive

He has seen it work through two startups; even Facebook went through an early survival phase before building for the long term

Scope: first-time founders eventually figure it out

43:32 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

Jean-Michel Lemieux · Mar 20, 2024

What Shopify and Atlassian share is founders playing a long game and being excellent at marketing

Long-game decisions kept them alive longer, and Harley, Mike and Scott understood the value of getting eyeballs

6:28 20Product: Why Process is Killing Your Product Team and How to Remove it | Three Product Decisions Every Team Needs to Make | Why the Best Companies Build Movements and Lessons from Shopify and Atlassian on How to Do It Right with Jean-Michel Lemieux

Kevin Hartz · Jul 22, 2024

Founders and investors should build for where the market will be three to five to seven years out rather than copying what is working right now

Human nature is to look at what's working today and produce memetically duplicative companies; the real failure mode is not looking far enough ahead

41:16 20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*

Gokul Rajaram · Mar 16, 2026

DoorDash's decision to take no revenue share from restaurants for a month at the start of COVID was the right long-term call despite being extremely painful short-term.

Restaurants were shut down and DoorDash had balance-sheet cash it could deploy to keep them open.

Scope: DoorDash was still private at the time

9:04 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

Tobias Lütke · May 4, 2026

Taking a long-term perspective changes the base framing of every challenge, because investments in developing people compound and accrue back to what you're building.

Sitting with people, helping them become the best version of themselves and giving them the hardest task they can manage only pays off if you're around long enough to capture the benefit.

5:35 20VC: Shopify's Tobi Lütke on How AI is a Scapegoat for Mass Layoffs & What Will Labour Markets Be in the Future | Why We Need More Scrutiny on Charitable Giving, Governments are Bad at What They Do and Trump Derangement Syndrome in Canada

Howie Liu · Aug 25, 2023

Software companies should pair long time horizons with the discipline of holding themselves to dated milestones — a sequenced long-term plan with revenue and transition milestones

Milestone discipline works as a self-fulfilling prophecy, as it does for hardware companies like SpaceX and Tesla that can't say 'we'll figure it out' while burning cash

Scope: acknowledges predicting a company's path usually doesn't work because of volatility and factors outside your control

32:28 20Product: Enterprises are not Adopting AI Yet, When Will AI Break Into Enterprise, What are the Blockers, What Do Enterprises Need from AI & Why Services Companies Will Win in the Next 10 Years of AI Implementation with Howie Liu, Founder & CEO @ Airtabl

Mike Cannon-Brookes · Oct 13, 2025

Companies must form explicit multi-year hunches about how the world will evolve, reassess them roughly every quarter, and be willing to abandon them

You cannot operate in this era saying you're not sure what's going on, but the environment changes fast enough that convictions must be revisited

18:23 20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

Harry Stebbings · Dec 6, 2024

Building a media and venture business is a forty to fifty year game and should be planned on that time horizon

He thinks in unusually long time horizons rather than planning to step back

61:11 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov

Jack Zhang · May 27, 2025

Committing your entire life — decades — to building one company is the right ambition for a founder

Patrick told him he would build Stripe for the next twenty, thirty, forty years, which Jack had never heard from a founder and found deeply inspiring

Scope: framed around building real economic infrastructure that impacts millions of businesses

59:32 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Harry Stebbings · Aug 22, 2022 · hedged

Planning a hundred years out can be futile and even limiting because things change so much

the world changes too much for long-range plans to hold

Scope: posed as a question to the guest

13:19 20VC: Why Market Always Wins Over the Founder & Why I Do Not Do Market Sizing | Why it is not the Best Time to be Investing but it is the Best Time to Have a Fund & The Type of Deals to do Today | Why The Best Founders Have 100 Year Plans with Wes Chan, C

Noam Shazeer · Aug 31, 2023

It is roughly impossible to predict where any company will be in ten years, so the important thing is to stay agile

The technological improvement between now and then will be so large — like being asked in 1900 where a company would be in 2000

31:22 20VC: Spending $2M to Train a Single AI Model: What Matters More; Model Size or Data Size | Hallucinations: Feature or Bug | Will Everyone Have an AI Friend in the Future & Raising $150M from a16z with Noam Shazeer, Co-Founder & CEO @ Character.ai

Kieran Flanagan · Jul 11, 2025

His usual growth rule — if an experiment can't show a success metric in six weeks it isn't worth doing — should not be applied to core AI bets like personalization, which need a longer concerted commitment

HubSpot's AI email personalization and auto-prospecting took around ten months to work, with the first months producing poor results; enforcing the six-week rule would have killed it

58:02 Ai bets warrant a longer commitment horizon than standard six week experiments

Wesley Chan · Aug 22, 2022

Truly visionary founders have hundred-year plans and know what the world looks like in a hundred years, even though the plan will not play out as envisioned

Larry and Sergey, Canva's founders, and Flexport's founders all had such plans and adapt them as they go — that knowledge is the differentiator

13:26 Founders with genuine hundred year plans hold a differentiating long term vision even if it wont play out exactly

Aravind Srinivas · Jun 15, 2026

Asking how a ten-year task could be done in ten months gets you much further than accepting the ten-year timeline, even if the compressed timeline proves impossible

The framing forces you to find the constraints instead of taking the default duration for granted

58:24 Compress the timeline to expose the real constraints

Jeff Lawson · Jun 28, 2021

Scaling well as a founder comes from thinking about the organization you will be in twenty-four to thirty-six months and building the leaders and mechanisms to fill those gaps ahead of the challenges you see coming

The times he has done this well were when he planned ahead of the coming challenges rather than reacting

16:29 Scale ahead by building leaders and mechanisms 24 to 36 months before need

Adam Foroughi · Apr 27, 2026

Nothing you decide today can change the outcome of the next twelve months — the present is already determined by past decisions; today's work only moves outcomes one to five years out.

He plans three to five years forward and works backwards; current results are the product of earlier choices.

68:31 Near term outcomes are already locked by past decisions

Guy Podjarny · May 24, 2023

If you cannot rationalize why your company's core value proposition will be more needed in five years, you should pick a different idea

You won't be at any real scale before then, so five years out is precisely when your idea should be most needed

10:12 Test idea viability by projecting five year necessity of the value proposition

Guy Podjarny · May 24, 2023

Founders should operate on 'big vision, small steps': know the destination and the next one or two steps, and only take steps you wouldn't regret if you got stuck on them for years

You can't know the path past the next couple of steps, so if you stall you should still be left holding something of value and able to continue or change path

11:13 Big vision small steps take only reversible steps toward a known destination

Aman Narang · Aug 21, 2024

Expansion across segments, geographies and platform should be sequenced over a decade rather than compressed into a single year

You underestimate what you can do over a decade but overestimate what you can do in a year, so it is a long game

44:16 Expansion should sequence over a decade not be compressed into a year

William Hockey · Dec 2, 2022 · hedged

Startups are extremely hard and the world moves slightly slower than people expect, so companies take longer to build than founders think

His own experience — he expects to be doing the same thing in ten years with more gray hair and several breakdowns along the way

48:25 Companies take longer to build than founders expect because the world moves slower than expected