What if the wisdom of one of Silicon Valley’s legendary leaders was sitting on your desk, any time you needed it? Maynard Webb’s rèsumè reads like a who’s who of tech darlings through the ages — CIO of Gateway, COO of eBay, CEO of LiveOps, and most recently the managing partner of the Webb Investment Network (WIN) — and “Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business” is exactly that.

Our team at Koan has had the incredible good fortune to count Maynard as a mentor and friend since day one. We had some idea what to expect when we chose “Dear Founder” for our most recent Book Club, but it didn’t disappoint. As a growing startup, many of the letters hit close to home; even those less applicable at our present scale touched on situations we’ve experienced through the eyes of our customers.

Letters of our own

We use Koan’s Book Club to explore all sorts of great leadership practices. Each installment goes as you’d expect: we read the book, share our learnings, and discuss where best practices can fit into both our day-to-day work and the broader Koan ecosystem. But Dear Founder’s a different sort of book, and this time we wanted to try something a little different—in this case, a small, individual assignment.

1. Read “Dear Founder”
2. Pick 2–3 of the letters in the book that feel most relevant to Koan
3. Write a short letter recommending them to a new hire

One of the great things about the sort of team that would build a leadership platform is our near-pathological obsession with initiative, leadership, and getting things done — even when things mean going just a bit above and beyond. On top of our usual, lively conversation, we ended up with a nice collection of thoughtful letters and a few recommendations of our own.

Koan’s Recommendations

Out of all of the letters Maynard Webb shares in “Dear Founder”, three came up time and again:

• “When you’re afraid you might be a ‘tweener’”. Even massively successful companies pass through a “tweener” phase on their path from early traction to massive growth. The interest is there, but the trajectory isn’t, and as Koan CEO Matt Tucker put it, this letter was “a good reminder of why we’re in this; Koan exists to be a breakout company. Full stop.” Being a “tweener” is part of life. The important thing is not to get stuck.
• “When you need to go from good to great”. Positive feedback gives our team a great boost, but what we’re really after are those terrific outcomes that get Koan’s customers singing our praises in the streets. This letter’s warning against complacency resonated with our team. As Ashwin Bhat from Koan’s dev team wrote, “we’re in a position where we have a lot going for us, but it’s ours to lose.”
• “When you need to improve execution”. Of course this letter resonated: helping our customers improve execution is what Koan does! Developer Randall Gordon summed it up nicely: “it reads much like a list of high-level ‘Dos’ that Koan either directly implements or attempts to actively reinforce. Set objectives? Check. Measurable key results? Check. Quickly identifying issues? Check. Reflecting on outcomes? Check!”

These are just the sort of recommendations you’d expect from a team building a world-beating leadership platform. Good traction and great feedback? Fantastic. Now, how can we get even better?

And in “Dear Founder”, we found the beginnings of an answer!