How much of career and startup success is luck versus deliberately engineered?

Ophelia Brown · Mar 17, 2023

99% of building a fund or a company is sheer determination and perseverance

In her own raise there was simply no option other than getting to a first close

43:46 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

Bastian Lehmann · Apr 8, 2024 · hedged

He doesn't much believe in luck and leans instead toward determination and grit, though he has no definite answer

Scope: admits he has no definite answer

4:28 20VC: Postmates Founder Basti Lehmann on How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN, Why Great VCs Add No Value and VC Value Add is BS Marketing & Why The Biggest Companies in History Will be Born Today and Replace Incumbents

Eléonore Crespo · May 9, 2025

No successful founder is lucky — building a company is far harder than outsiders think and founders work harder than anyone.

People attribute company success to luck without seeing the work involved.

60:50 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Craig Courtemanche · Dec 4, 2023

Procore's success is attributable mostly to persistence and luck, with skill ranking lowest

Single chance moments — a family friend knocking on his door with a tech job, the irrational decision to wind down a profitable business for Procore — determined everything; change one and none of it happens

Scope: counts persistence as a skill when pressed

62:55 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

Markus Villig · Nov 13, 2024

Bolt's success was close to 100% luck

Without Oliver, who happened to answer a random forum post, the company would never have reached where it is

Scope: speaking about his own company's case

12:44 20VC: Bolt; The Most Insane Story in Startups | Turning a $5K Loan into an $8BN Company | Why Every VC Turned Down One of Europe's Biggest Winners | Competing with Uber & The Future of Micromobility and Self-Driving

Harry Stebbings · Jan 5, 2026

In order of importance for founder success: luck, then talent, then timing

49:02 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Sahil Bloom · Feb 25, 2022

Luck is largely engineerable: what people call luck is usually the macro result of thousands of consistent micro actions that put you in the right situations.

His own break — six months of daily 5am gym conversations with Tim Cook that became a key mentorship — came not from being impressive but from consistently showing up with no end goal in mind.

Scope: distinguishes engineered luck from 'true luck'

21:56 20VC Exclusive: Sahil Bloom on Raising his Debut Venture Fund (SRB Ventures), Why Traditional Venture Firms Are Going to Lose and How Sahil Built a Twitter Audience to 500K+ in 18 Months

Brian Halligan · Jan 15, 2024 · hedged

Career success is roughly half preparation and half luck, and well-prepared people tend to end up in the right place at the right time

He has always been over-prepared for everything, and observes a high correlation between preparation and lucky positioning

Scope: 'maybe' half and half; reflecting on his own career after his first job

6:51 20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?

Sanjit Biswas · Dec 8, 2023

Samsara could only sustain its operating intensity and speed because it was a second-time team — a first-time team would have blown apart

Pattern matching meant they recognised product market fit without questioning it, and people matching meant they could re-recruit known colleagues into known role fits when scaling sales

34:21 Repeat team pattern and people matching enables speed

Sanjit Biswas · Dec 8, 2023

Serial founders carry a selection-bias effect: many who've been through it once won't fully re-commit, so the ones who do opt in wholeheartedly are especially powerful — but you shouldn't filter out first-time founders

Some second-time founders are reluctant or want to do it lightheartedly; meanwhile first-timers like Jensen Huang, Zuckerberg and Toby Lütke are phenomenal and you wouldn't want to miss them

35:33 Committed second timers are strongest but first timers still win

Zaria Parvez · Jan 19, 2024

Her success is roughly 20% luck (access and opportunity) and 80% hard work, and could be replicated by anyone given the same access and opportunity

She had a supportive family, a good college, internships, and landed at a brand willing to take risks and post trending audio — all access she then took advantage of

32:29 Luck is only access the rest is replicable work

Klaus Hommels · Nov 27, 2024

If you behave ethically and generously, luck comes back to you and losses can be turned into positive outcomes

Job rejections from Goldman and McKinsey saved his life; and the Wunderloop failure introduced him to a buyer with whom he later founded Mekafoni, sold to Naspers for $150m, more than overcompensating the loss

54:34 Ethical generous behavior returns as luck that recovers losses

Kevin Ryan · Apr 10, 2024

Luck plays a real role in startup outcomes because material factors are outside the founder's control

Serial founders with 20 companies never have 20 successes; Gilt hit $500M revenue in four years but became unprofitable once the whole fashion industry started discounting online — a dynamic outside their control

5:38 Material factors outside founders control shape startup outcomes

Stephane Kurgan · Jul 28, 2023

The most useful thing a professional can do is accumulate skills, knowledge and network so they can seize an opportunity when it appears, since luck is the meeting of opportunity and preparedness

Luck matters enormously in business but is not controllable; preparedness is the only part you control, so when opportunity knocks you can execute against it

36:15 Luck is the meeting of opportunity and preparedness so accumulating skills and network is what you control

Shyam Sankar · Jan 17, 2024 · hedged

The most productive mindset is to assume you have good luck and focus on hard work, since work is the only variable you control

Believing your luck can vary isn't productive; only one of the two variables is under your control

6:00 Assume good luck exists but focus on hard work since effort is the only controllable variable

Harry Stebbings · Jan 17, 2024 · hedged

The role of fake humility has been overvalued; many successful people are happy to admit to themselves that they got where they are largely by working extremely hard

People are happy to admit to themselves that they worked their asses off, but won't say it publicly

6:35 Private belief in hard work is suppressed by public fake humility norms

Chris Sacca · Oct 11, 2021

Investors should invert their instinctive attributions: treat gains as luck and losses as a lack of talent that demands more work.

The natural instinct is the reverse — crediting genius on the way up and blaming bad luck on the way down — which prevents learning.

6:41 Invert natural attribution credit luck for wins blame effort for losses

Chris Sacca · Oct 11, 2021

Success is luck but not an accident — it correlates with extra work, insight and commitment, while also depending on dozens of single points of failure outside one's control.

Looking back he can identify both effort and insight behind wins and arbitrary introductions or gut calls without which nothing would have happened.

8:30 Success is luck that correlates with effort insight and commitment not pure accident

Antoine Le Nel · Oct 18, 2024

Candy Crush's success was not mainly luck; King won because it tested everything extensively as a volume game and shipped games at an extremely fast pace

They understood early that if you try as many things as you can, at some point something picks up; the rate of producing and releasing games mattered more than any individual hit

3:29 Systematic high volume testing not luck drove candy crushs success

Tom Hulme · May 8, 2024

What looks like luck in great investors and founders is mostly the product of a deep network — serendipity favours the connected

Successful people almost always have an incredible network around them, and by Metcalfe's law network value rises with the square of the number of nodes; his own career came from being in a network of amazing people plus staying optimistic and grabbing opportunities

31:54 Luck is explained by deep network serendipity favors the connected

Craig Courtemanche · Dec 4, 2023

Literally anyone can be successful if they follow what they believe in and get the required amount of luck

62:26 Anyone can succeed given belief and enough luck

Christa Quarles · Jul 29, 2021

The biggest lie rich people tell themselves is that their success wasn't luck but rather that they are simply that much more capable than everyone else

Luck is preparation meeting opportunity, and where and when you were born feeds heavily into how success and money come to be

41:13 Rich people falsely attribute success to skill rather than luck

Eric Vishria · Sep 25, 2024

You cannot judge in the moment whether an outcome was lucky or unlucky — good and bad only resolve in the fullness of time

The Chinese parable of the horse and the draft, applied to RockMelt: they didn't realize the potential they wanted, yet he couldn't be happier where he ended up and his old team landed at great companies

55:09 Luck and outcome can only be judged with hindsight not in the moment