Executing Outside-the-Box
Occasionally, I’ll see founders who want to do everything differently. I admire their courage. If they are quick learners, this type of founder has tremendous potential.
More commonly, I’ll see founders who want to do everything by the book. This approach seems reasonable. On average, I think a startup will do better in a specific area by following the best practices playbook instead of setting it on fire.
But I think the founders most likely to build an iconic tech company will execute both inside-the-box and outside-the-box. Ideally, they understand best practices and then intentionally decided to veer from them. 1
Stripe is a classic example of getting this right. Early on, they went physically on-site with users to install their software. That was an unheard of tactic for a cloud software company. At the same time, they followed conventional practices such as focusing on making a beloved product and in seeking to hire top talent.
Many of today’s top tech companies went outside-the-box at the early stage and found tremendous success:
Palantir: early on, they rejected the ubiquitous GTM strategy of hiring retired generals to help win defense contracts. Instead, they relied on the sales charisma of key executives, notably CEO Alex Karp. This worked like magic.
Canva: they didn’t hire a sales person until over $100m in revenue. They were nailing product-led-growth many years before the term was coined.
Zapier: they built an SEO-driven go-to-market motion when SEO was frowned upon by Silicon Valley’s cool kids. They raised all of $1.4m to reach unicorn status.
Of course, these strategies aren’t so contrarian any more. What are the unconventional strategies that today’s savviest early stage startups are using? Let’s check back in a few years to see. Undoubtedly, many of the most successful startup will have nailed both inside-the-box and outside-the-box strategies.
The one area where I’d caution against ever going outside-the-box is in practicing user empathy. Sometimes, founders with outside-the-box inclinations might want to blame users for not “getting it.” This mindset can create a major drag on finding product-market-fit.