Six for February 10

Welcome new subscribers! Here’s six more actionable startup reads for you.

Trust Issues // Trust, Ben Kuhn, says is the main bottleneck for teams being effective while they grow. Kuhn, an engineering leader at AI giant Anthropic, explores trust deficiency and the many ways it manifests in slower work and missed outcomes. He also offers specific remedies for trusting others more, and for getting them to trust you. link

Interested in trust and teams? Spoiler alert: absence of trust is one of the Five Dysfunctions of a Team, according to Patrick Lencioni.

More Shipping, Less Planning // They don’t use product roadmaps at Ashby. The Series-C startup that’s disrupting the talent space doesn’t expend effort on longer-term feature planning that they admit is just as likely to end up being right as it is wrong. Instead, they focus on shipping often and plan effort investment by product area instead of by feature. This allows them to be far more nimble in responding to emergent customer needs, as well as shifts in technology and market demand - it also reduces time spent in planning meetings. link 

More Planning, Less Shipping // Big projects always take longer and cost more than expected because teams move too quickly to start building, and don’t plan enough. Bent Flyvbjerg, economist and megaproject expert, details this phenomena in his book How Big Things Get Done. It’s a stark reminder that we must consider the type of challenge we’re facing before we decide whose advice to follow. What’s true for constructing an opera house might not apply to my SaaS application, but it’s still worthwhile to understand the pitfalls of big projects so we don’t fall prey to them. link

Why do big projects break ground before planning is done? Robert Moses discovered that while big budget requests were often hard to get through, budget officials were loathe to cut funding to projects that were already in progress. His strategy was to get enough funding to get started, and then ‘realize’ they needed more money once the shovels were in the ground. Read more about Moses’ devastatingly effective tactics in The Power Broker.

Winners Need Not Apply // Venture capitalists only pick winners 2.5% of the time. So says Clint Korver, co-founder at Ulu Ventures, who explains that VCs aren’t in the business of picking winners, but instead that of assembling portfolios that achieve profitability by boosting the chance of containing outliers (think unicorns like Airbnb, Google, etc). For founders going out for investment, understanding this distinction can be instructive for pitching, as well as knowing the motivations of your investment partners. link

Decision Intrigue // There is a science to making good decisions. When you’re a founder, a leader, or a builder, you’re constantly making impactful decisions. Shane Parrish wrote a great starting point for delving into the world of decision-making processes. As far as primitive skills go, you’d be hard-pressed to find one as broadly applicable as decision-making. link 

Fixer Upper // Things break. Knowing which ones to fix, and when to fix them, is the hard part. David Cain argues that broken things incur costs beyond their direct expense, weighing also on our psyches. His plan: allocate time to fix three things per week; it’s often easier than you think it’ll be, and the relief that accrues will be well worth the effort. link

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Six for Startups is compiled each week by me, Isaac Krasny. I’m a veteran startup product leader, founder, & CPO. I’m currently the product advisor for the GrowthCraft Startup Community and a coach and consultant helping guide founders to product-market fit.