As Risky As It Gets, 2012 to present

Writing

92 essays about companies, risk, management and life.

Search the archive92 essays

2026Don’t Do Brazilian Jiu JitsuLife & practice · 3 min

2026My Own Private Midlife CrisisLife & practice · 2 min

2026You don’t need a new board member. Most of the time.Leadership · 1 min

2025Slack and email aren’t going anywhereLeadership · 3 min

2025An Introduction to Gustavo Batista’s Guard PassingLife & practice · 4 min

202411 yearsBuilding companies · 2 min

2023Generations of foodLife & practice · 2 min

2023All I have is timeBuilding companies · 1 min

2022Founders, normies, conformismLeadership · 2 min

2022The life cycles of tech executivesLife & practice · 3 min

2022Side questsLife & practice · 2 min

2021The visionary and the desperate (3 observations on how early products get traction)Fintech & risk · 2 min

2021Bad monkeyLife & practice · 3 min

2021Slaying dragons for fun and profitFintech & risk · 1 min

2021The worst type of career advice (although it’s given in good faith)Leadership · 2 min

2021The cages we build for ourselvesBuilding companies · 5 min

2021Nothing matters and we’re all going to dieLife & practice · 2 min

2021White belt, black beltLife & practice · 2 min

2021How to be less boring in panels and podcastsLife & practice · 2 min

2020Staying sane as an executive in hypergrowthFintech & risk · 2 min

2020Two approaches, one culture.Fintech & risk · 2 min

2020On the moral authority of the founding CEOBuilding companies · 8 min

2020Why I look up to Miki HalikaBuilding companies · 4 min

2020Let’s talk about luck in startups.Life & practice · 2 min

2020Raising defensively: founding companies without losing themFintech & risk · 12 min

2020EquifinalityBuilding companies · 3 min

2020A warrior walks into a room: startup founders right nowLife & practice · 1 min

2020The decade of ShouldLife & practice · 2 min

2019CEO dinnersBuilding companies · 2 min

2019Founders, VC funding won’t save youBuilding companies · 3 min

2019What’s a Chief of StaffLeadership · 2 min

2019About finding your placeLife & practice · 4 min

2018My talk for TrueAccord’s 2018 Holiday partyBuilding companies · 4 min

2018What happens after you’re hotBuilding companies · 2 min

2018MercenariesLeadership · 2 min

2018Solving problems when growing is more complex. Here are some ideas.Leadership · 3 min

2018Staying on the rollercoaster gets easier over timeBuilding companies · 2 min

2018Why I’m back to bloggingBuilding companies · 1 min

2018People are basically goodFintech & risk · 2 min

2018Subprime Blindness is holding back the next big break in fintechFintech & risk · 2 min

2018Power doesn’t corrupt.Life & practice · 3 min

2018The 50% ruleLeadership · 2 min

2018Why work for a Series B startupLeadership · 2 min

2018MotivationLife & practice · 2 min

20184th of JulyBuilding companies · 1 min

2017About leavingFintech & risk · 3 min

2017With great power comes… a great misunderstandingLeadership · 2 min

2016Why I Can’t Get Behind John Oliver’s Latest Debt Collection PieceFintech & risk · 4 min

2015Why Start a Company in a Regulated Industry?Building companies · 4 min

2014I really want Apple Pay to fail. So much.Fintech & risk · 3 min

2014Hiring inexperienced employees helps me beat the talent wars. Here’s how I do it.Fintech & risk · 4 min

2014My answer to “How are you doing?” and hacking the startup CEO gameBuilding companies · 2 min

2014STARTUPS DON’T GET SOLD. THEY GET BOUGHT.Fintech & risk · 5 min

2013Dealing with Account Take Over? Here are my top tips (O’Reilly post)Fintech & risk · 1 min

2013Working on risk and fraud prevention? Don’t dig your career into a holeFintech & risk · 3 min

2013Why did PayPal buy Braintree?Fintech & risk · 1 min

2013TrueAccord is looking for a community managerFintech & risk · 2 min

2013BitCoin mass-adoption challengesFintech & risk · 4 min

2013The top 8 reasons you have a fraud problem – my talk at BalancedFintech & risk · 1 min

2013Risk Management Talk, July 11th at Balanced’s officeFintech & risk · 1 min

2013How to get the most out of your acquired entrepreneurBuilding companies · 4 min

2013Babylon’s bait and switch (updated)Building companies · 4 min

2013Payments: What is the best career play in payments today (Jan 2013)?Fintech & risk · 1 min

2013Online and Mobile Payments: What are the risks of mobile POS systems?Fintech & risk · 2 min

2013How does TripAdvisor and Yelp detect fake reviews?Building companies · 1 min

2013Israeli Culture: Why are Israeli people so hard to work with?Leadership · 3 min

2013Payments: Why does the payment industry lack technical and UX innovation?Fintech & risk · 2 min

2013Salvaging some Quora answersBuilding companies · 1 min

2013Why using Bitcoin is like abstinence, and other thoughts about cryptocurrency and financial systemsFintech & risk · 4 min

2013Fraud in Digital Goods Sales 201 (Signifyd post)Fintech & risk · 3 min

2013How does paypal’s fraud detection compare with other other money exchange services/banks?Fintech & risk · 1 min

2013PayPal, Lenovo and killing the passwordFintech & risk · 3 min

2013Don’t pitch me, bro: 4 common payment startup ideas that you should avoidFintech & risk · 4 min

2013Using social network data in fraud preventionFintech & risk · 4 min

2013Smart, non-techie people sought for new projectFintech & risk · 2 min

2013Lost knowledge and failing teams: how managers undermine successful culturesLeadership · 4 min

2013Getting advisors on board: a few practical tipsLeadership · 3 min

2012What are the risks of mobile POS systems?Fintech & risk · 1 min

2012Why isn’t anyone using MoneyBookers?Fintech & risk · 1 min

2012An Englishman (or Israeli) in the Valley: why lingo matters when you pitchFintech & risk · 3 min

2012Forget Big DataLife & practice · 1 min

2012Even good things come to an end – Why I’m leaving KlarnaFintech & risk · 3 min

2012What does the Google Wallet Card mean for the mobile payments industry?Fintech & risk · 1 min

2012Feature companies in risk and fraud (or: enterprise and consumer startups are different)Fintech & risk · 4 min

2012Vouch for me: social collateral and voter fraudFintech & risk · 3 min

2012Apple’s iPhone 5 and Why NFC Doesn’t MatterFintech & risk · 1 min

2012Smart risk management: why the “factory” approach could bring you downFintech & risk · 5 min

2012Why hasn’t Venmo succeeded?Fintech & risk · 2 min

2012What’s Missing in Data Science TalksFintech & risk · 4 min

2012In Defense of Knowledge Sharing in Fraud PreventionFintech & risk · 3 min

2012What Winning in Payments Should Mean, and How to Stay Away from the 0% Interchange TrapFintech & risk · 3 min

2012Why we’re going to hit 0% interchange, and why it’s all a big spinFintech & risk · 4 min