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Risk, failure and advice

Bets that did not pay off, and the recurring warning that no piece of advice, including this collection, transfers cleanly.

38 entries from 23 named voices

Most popular

Opinion From a top issue

Learning, growth and network compound over a career and matter more for long-term success than jumps in job title.

Missing out on a role because the title is not senior enough optimizes for outside perception; areas of learning have compounding effects titles do not.

Zoe Jervier Hewitt, Talent Partner, Sequoia Capital

Opinion From a top issue

Startups should sell climate technology to authoritarian regimes because every country must transition to fossil-free transport, regardless of politics.

Hasselskog defended Candela's €20m electric-boat deal with Saudi Arabia's Neom project, its largest order, against criticism over Neom's human rights record.

Gustav Hasselskog, Founder & CEO, Candela

Opinion Most watched episode

Staying silent about wrongs to protect your climb toward influence is a bad trade; keep your morality intact even at a price.

Dada has empathy for peers who defer speaking up until they are rich enough to matter, but rejects the logic. Having grown up without money in a high-rise with two siblings, she says she would rather return to that than suck up to an authoritarian turn for comfort.

Judith Dada, General Partner, Visionaries Club · Episode 58

Everything in risk, failure and advice

Takeaway

Prevent set-and-forget OKRs with built-in cadence: weekly or bi-weekly team check-ins with digital documentation, leaders auditing the update logs, a monthly leadership review where every OKR owner presents, and a mid-cycle retro.

Set-and-forget is the typical failure point. Add ambient visibility: talk about OKRs in one-on-ones and hallways, print them on the office wall, or run them on a screen; one client cycled team OKR progress on an office LCD like a screensaver.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes · Episode 31

Takeaway

The single highest-leverage OKR action for a founder: get people into the same room to set OKRs together, creating vertical alignment with company direction and horizontal alignment across teams.

Silos set OKRs in separate rooms without knowing each other's priorities. Leadership gives direction first (vertical), then workshops between teams create the horizontal alignment; shared spreadsheets let teams see and comment on each other's drafts.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes · Episode 31

Takeaway

Integrate action planning into your OKR framework: teams miss perfectly set goals when nobody plans how they will be achieved and what is required from other teams or leadership.

Lack of action planning is a surprisingly common reason organizations discover too late in the cycle that they are falling short.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes

Takeaway

Use the regret minimization framework for hard calls: years from now, which choice would you regret not making?

It is why Alex Limpert started GuestReady and chose to start a family; the frame prioritizes long-term action over fear.

Alex Limpert, Co-founder and CEO, GuestReady

Takeaway

Never try to beat a game; break it and invent your own: in outlier-success spaces it is better to be unique than 'same but a tad better', combined with a ton of work and long-term thinking.

Andreas Klinger, Founder of the EU Inc initiative; investor, Prototype Capital

Insight

The migrant founder edge is structural: typically no vitamin B network for the first 100K, no family safety net, and no plan B, which forces exactly the all-in hunger that predicts founder success.

Growing up between two cultures also trains resilience and instant switching of language and mindset. She contrasts this with consultants who pick a company to found by market-size analysis, which she is allergic to.

Gülsah Wilke, Partner, DN Capital; co-founder, 2hearts · Episode 69

Insight

Regulatory risk grows with scale and can kill a market overnight: Singapore changed short-term rental rules from one day to the next and GuestReady had to stop its business there immediately.

Early on the team assumed that if Uber and Airbnb could route around regulation, they could too. After the Singapore lesson, monitoring and anticipating regulation became a key input to strategic planning. Broader point: at the start a startup has almost no downside risk, but as you grow the downside grows and deserves scenario planning.

Alex Limpert, Co-founder & CEO, GuestReady · Episode 34

Insight

OKRs complement KPIs and never replace them: KPIs are the car dashboard you always watch, OKRs are the temporary route you pick each cycle, and key results for new initiatives often graduate into new KPIs.

You cannot throw away the dashboard to focus on the GPS. KPIs monitor ongoing health and rarely change; OKRs change every two to four months based on priorities. Existing KPIs can show up inside key results, which is fine, but the two serve different jobs.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes · Episode 31

Insight

The three most common OKR failure modes: adopting for invalid reasons (the CEO read Measure What Matters, a competitor does it), letting HR run OKRs as a performance evaluation tool, and losing discipline after an enthusiastic first cycle.

OKRs belong to the strategy domain, not HR. Founders need skin in the game to keep the framework alive; clients who dropped the ball cite being busy, and their OKRs decay into a huge spreadsheet with no spirit in it.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes · Episode 31

Insight

yamo's collapse traced a concrete macro chain: Russian gas made its German manufacturers demand higher prices while German food inflation hit 17-19%, so retailers shelved everything that was not discount-priced.

After growing nearly 100% year on year, the second half of 2022 broke the model: consumer confidence in the main market plummeted, retail partners focused purely on price, and a premium newcomer could not grow as planned despite a solid Swiss business.

Tobias Gunzenhauser, Co-founder and former CEO, yamo · Episode 28

Insight

The moat of the eight global food giants is simply decades of physical and digital infrastructure investment, and any challenger must make those fixed investments too, which then forces a growth pace it has to sustain.

Serving dozens of retailers across 3,000 stores in seven markets under food regulation means playing the incumbents' game as it is played. The infrastructure only pays if you keep growing fast; when the macro stops the growth, the fixed base becomes the trap.

Tobias Gunzenhauser, Co-founder and former CEO, yamo · Episode 28

Insight

Unicorn founders typically worked at a startup first, had about 10 years of mostly product and engineering experience, and lived, worked, or studied abroad.

Endeavor study of 200 unicorn founders; they did not come from business schools or consulting firms. The blueprint: work at a startup, learn to build, see the world.

Tech Roundup, Feb 18, 2025

Insight

China's startup ecosystem collapsed under the state crackdown: 1,202 startups were founded in 2023 versus 51,302 in 2018, with VC investment nearly gone.

The crackdown began around Jack Ma's disappearance from public view in 2020; funds originally dedicated to China now seek targets in other regions, potentially benefiting Europe.

Tech Roundup, Sep 17, 2024

Insight

Competing with legacy giants at scale requires massive infrastructure investment, and when growth stalls, the fixed costs kill you regardless of intentions.

yamo scaled across seven European countries but could not sustain the infrastructure cost of competing with established food companies without matching growth.

Tobias Gunzenhauser, Co-founder and former CEO, yamo

Insight

OKRs are not a substitute for strategy; they work best when guided by a clear, shared direction.

Treating OKRs as a workaround for not having a strategy is one of the biggest missteps companies make.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes

Insight

KPIs measure health while OKRs drive focused change; confusing or substituting one for the other produces vanity metrics and misaligned goals.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes

Insight

Adding 1-2 percent Bitcoin and Ethereum historically doubled portfolio returns with only marginal volatility increase, due to low correlation with traditional assets.

Huegli frames small crypto allocations as an asymmetric-return play rather than a conviction bet; creeping institutional adoption will compress future outsized gains.

Pascal Huegli, Crypto analyst and educator, Maerki Baumann

Opinion

Most startup advice should be ignored because it is riddled with survival bias; your own judgment about your context is the better instrument.

Advisors typically recommend whatever worked for their own company (go to the US, do product-led growth) without accounting for context. By definition an innovative startup does something no one has done before, so playbooks from other companies only go so far.

Melanie Gabriel, Co-host, Follow the Gradient; Co-founder Yokoy; Co-director and CEO, ETH AI Center · Episode 54

Opinion

You do not need a strategy document to start OKRs: 80-90% of founders he asks have none or an outdated one, yet they know their top priority for the next three to four months, and that is enough.

A one-to-three-year strategy is best practice and ideal, but its absence should not block OKR adoption. What you do need is clarity on the next three to six months and, ideally, baselined metrics and KPIs to plug into key results.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes · Episode 31

Opinion

Gen Z entrepreneurship is driven by lost optimism: without the millennial sentiment that everything gets better, building becomes the answer to feeling helpless about big problems.

He pushes back on the lazy-Gen-Z cliche: in Berlin he met many young people who want to change something rather than watch the news and despair. The generational backdrop of large unsolved problems can itself be the motivation to build.

Nils Feigenwinter, Co-founder and CEO, Bling · Episode 16

Opinion

In entrepreneurship, done beats perfect: the 80-20 principle is far more crucial for a founder than it ever was in consulting.

Christina names learning to simply get things done as her biggest transition challenge from consultant to entrepreneur.

Christina Stahl, Co-founder, AMELI Zurich · Episode 13

Opinion

Outcomes are a function of execution, strategy and luck, and luck's share is growing as everyone's execution and strategy improve.

Dan Hockenmaier, Strategy leader (ex-Faire)

Opinion

Entrepreneurship must offer a realistic chance to earn more than a regular job; otherwise call it a hobby.

Hustling to pursue a dream is fine, but benchmark the venture against a money mindset.

Tony Kula, Founder

Opinion

The advice founders should ignore is 'play it safe': no great story starts with playing it safe.

Vincent Martinez, Co-founder, Nanoleq

Opinion

Startups need bold but deliberate bets early, like a competitive skier pushing big jumps early in the season to win later.

Roman Hoelzl transfers his freestyle-ski mindset to RobCo: calculated risk is key to long-term success, and the skill is knowing when to go all in and when to hold back.

Roman Hoelzl, Co-founder and CEO, RobCo

Opinion

Take in all advice but match it against your own company data and personal gut feeling; you know your company best.

Roman Hoelzl, Co-founder and CEO, RobCo

Opinion

Ignore all advice that claims to be right for every situation; advice is always contextual.

What sounds dumb in one context may be exactly right in another; no advice lives in a vacuum.

Tuomas Toivonen, Co-founder, Holvi

Opinion

The biggest myth about failure is that there is no professional life after a shutdown; five to seven years of committed building compresses decades of corporate learning.

Tobias Gunzenhauser, Co-founder and former CEO, yamo

Opinion

Ignore anyone claiming there is one way to build a company; gather several competing perspectives and apply the learnings to your own situation.

Input from a scaleup or VC further ahead on the journey is useful, but copying their playbook one-to-one is unlikely to work for you.

Enzo Waelchli, Commercial leader, Anybotics

Opinion

Startups should not run OKRs from day one; the framework pays off once you scale past the MVP stage into departments or cross-functional teams.

Early implementation can stifle agility; timely adoption supercharges alignment.

Omid Akhavan, OKR coach and Founder, Lucid Outcomes

Opinion

Ignore just about all founder advice; the only pieces that hold ground are 'work really hard', 'don't give up', and 'add as much value as possible to your end consumer'.

Patrick Spychalski, Co-founder, The Kiln

Opinion

In the end, no outside opinion beats the gut feeling of a successful founder.

Nicole Buettner, CEO, Merantix Momentum

Opinion

Ignore any advice that goes against your gut feeling.

Fabienne Doerig, Finance and Operations leader (ex WeFox); building AI back-office automation

Opinion

Earnestness and obsession outweigh hype every time when identifying world-changing founders.

The best founders are not chasing status; they act on an internal drive often present since childhood and build from long-term conviction, not trend-chasing.

Kitty Mayo, CEO, Project Europe

Opinion

Ignore the advice to only do things you already know work well; that mindset kills ventures.

Thomas Dubendorfer, Angel investor and President, SICTIC

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