Scott Belsky in a leather chair gesturing toward Sean Blanda, with a "Pilcrow House" sign behind them

Lessons on “The Messy Middle” of business from Scott Belsky

You know startups. You know exits.

Most of the work of business takes place somewhere in between the very start and the very end. Yet a lot of media attention focuses on those two iconic poles. So you might know a lot less about the space between the two poles.

We need more guidance on the work stage. That’s the approach in The Messy Middle, a new book published late last year from Scott Belsky. He founded Behance, which sold in 2012 to Adobe for $150 million, and has been an active  investor.

I’ve known of Belsky through my close friend Sean Blanda, who worked at Behance. Blanda also hosted Belsky back in November in Phiadelphia for a fireside chat featuring themes from the book. It was the first of Blanda’s new event series he calls the Pilcrow House.

The book and the event are both worth a proper review. But I’ve sat on my notes since last month, and this week Blanda has his second event, so I wanted to share what stood out to me from hearing Beslky and starting his book.

Yellow cover 'The Messy Middle' book framed from a distance in an all-white background
The Messy Middle is a pretty canary yellow book with confirming and challenging thoughts

Here are some of the broad ideas that ring true to me:

  • We are not at our best at the lows or the highs. At the lows, we are often too scared to change. At the highs, we often don’t attribute success to right things.
  • Belsky is critical of how much we (media, peer networks, etc.) celebrate company financing news. There is a reason for it: for private companies, these are moments of external validation, but I certainly agree.
  • On financing: “For a strong strong company it’s a tactic. For a weak company it’s a goal.”
  • So why did Belsky raise a $6.5M round? “Because I was strangling growth. But we did it later stage so we could control the impact of it differently.”
  • “Money obfuscates real problems.” Uber is still spending more than it is making.
  • For hiring, what are some interview questions he likes? What are your interests and what have you done with it; Ask the same questions at each interview stage and see if the answers grow each step.
  • In a hyperconnected world, “maybe disconnection is a competitive advantage,” if a founder or CEO can find peace somewhere else to come back refreshed.
  • Every few days he has a block for creative time and plane time
  • Every organization needs a balance of both Alignment (design and images of progress and mission) and Process (meetings and documents). Too much of either is a problem.
  • “A prototype is worth a 1,000 meetings”
  • During every work session, “you need to be moving both pebbles and boulders.”
  • You want a company culture of “Disagree and commit,” in which teammates will express differences of opinions and then commit fully to the final decision, no matter what it is.
  • “When you place credit with a specific employee you give them influence.”
  • From starting, to the messy middle to whatever your company’s final state is, remember, “the last mile is a different business.”