How much risk should companies accept on unconventional go-to-market experiments?

Sam Blond · Apr 12, 2024 · hedged

Not all creative or crazy ideas will land, and it's better to have tried than not tried — failures should even be celebrated

The glass-half-full framing of a costly failed experiment

Scope: offered as a 'maybe' framing

63:58 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Andrew Dudum · Apr 4, 2026

Eucalyptus became the dominant player in Australia, the UK and Germany because its willingness to experiment, fail and refocus let it move faster than everybody else

Experimentation velocity and willingness to kill failing markets compounds into speed advantage

28:10 20VC: Hims & Hers: $4.3BN Market Cap on $2.3BN of Revenue: The Comeback | Why Being Public is 10x Better | The Death of the "Strategy" Hire | Why Performance Marketing is Worse than Brand Marketing with Andrew Dudum

Carles Reina · Apr 11, 2026

Go-to-market should be run like venture investing: test a hundred things expecting only three to six to perform

In venture you invest believing all will work and accept that only a few do; the same portfolio logic applies to markets, self-service, resellers, cloud ecosystem, grants and affiliate programs

20:38 20Sales: ElevenLabs: Why We Set a 20x Sales Quota | How to Structure Sales Compensation Plans | Customer Success: 'Total BS' or Growth Engine? | Building an AI Sales Machine: What Tools & Tactics Must CROs Adopt Today with Carles Reina

Harry Stebbings · Apr 12, 2024

Founders should run out-there contrarian experiments but cap the downside so failures don't run into the millions

Trying contrarian things is worth it, but the losses need a ceiling

64:19 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Kyle Norton · May 30, 2025

Spending hundreds of thousands of dollars on channel experiments that may fail is a correct cost of doing business; you think in bets and triple down on the winners

The world is probabilistic — some channels will work and some won't — and their CTV test only stopped because better-performing channels deserved the resources

Scope: CTV was abandoned for resource allocation reasons rather than proven failure

35:12 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Carles Reina · Apr 11, 2026

Budget should never be the constraint on new initiatives; the gate is whether a small, cheap experiment has proven the idea works before scaling

Give someone $50-200k to prove a thesis on the side; once results show up, scale it with all the budget they want — but don't commit a million dollars, a dedicated team, or six months of someone's time upfront

47:58 20Sales: ElevenLabs: Why We Set a 20x Sales Quota | How to Structure Sales Compensation Plans | Customer Success: 'Total BS' or Growth Engine? | Building an AI Sales Machine: What Tools & Tactics Must CROs Adopt Today with Carles Reina

Zaria Parvez · Jan 19, 2024

Social media managers easily lose sight of the weight of posting to millions of people and slip up, and crossing the line is often how you learn where the line is

It's easy to get lost in the sauce commenting and chasing viral content; she commented on something she shouldn't have and only then learned the boundary

Scope: framed as her own early mistake

23:07 20VC: How Duolingo Scaled to 8M TikTok Followers, How to Create Viral Content, Why Most Companies Suck at Content Marketing and How to Change & Why You Should Not Work with Content Agencies with Zaria Parvez, Global Social Media Manager @ Duolingo

Tobias Lütke · May 4, 2026

'You can just do things' — if you know what a good outcome looks like you should step outside the system and try, because the cost of action is lower than ever and action causes information

Systems exist to produce good outcomes, so where you can see the outcome you can bypass the system; and discovering why the system discourages something is itself valuable

Scope: only when the endeavour is completely victimless

60:47 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

Martin Gontovnikas · Feb 14, 2024

No company achieves exponential growth without problems and crazy bets, so taking big risks is essential to exponential growth

At Auth0, going from $40M to $80M ARR was impossible on the existing plan, so half of marketing and a big chunk of product focused solely on sign-ups and activation, dropping product marketing and launches; without that bet the company would have ceased to exist

4:13 Exponential growth requires big bets and accepting problems

Martin Gontovnikas · Feb 14, 2024

A 'culture of failure' amounts to not treating people badly for a well-set-up failed swing; the only firing criterion is whether they learned something

If they learned something they can iterate; if they learned nothing there's no value in the failure

6:51 No punishment for a well set up failure only for failing to learn

Sri Batchu · Jul 26, 2023

Growth work has an inherently high failure rate — roughly two thirds of projects will fail — so the goal is to fail quickly and conclusively rather than to avoid failure

Failure is the base rate in growth, so the controllable variable is cycle time to a conclusive result

0:00 High failure rate is expected so teams should optimize for fast conclusive results

Harry Stebbings · Dec 12, 2025

Marketing today is more forgiving of mistakes because attention is so fleeting that people forget things far faster than they used to

What is interesting today is not interesting tomorrow, so a failed experiment doesn't stick to you

12:02 Fleeting attention means failed experiments do not stick