/Scott Belsky — How to Conquer the Messy Middle (#336)

Scott Belsky — How to Conquer the Messy Middle (#336)

Photo by Eric Einwiller

“In the startup world, resources are like carbs. Resourcefulness is like muscle. When you develop it, it actually stays with you and impacts everything you do going forward.”
— Scott Belsky

Scott Belsky (@scottbelsky) is an entrepreneur, author, investor, Chief Product Officer of Adobe, and venture partner with venture capital firm Benchmark. Scott co-founded Behance in 2006 and served as CEO until Adobe acquired the company in 2012. Millions of people use Behance to display their portfolios, as well as track and find top talent across the creative industries.

Scott is an early investor and advisor in Pinterest, Uber, and Periscope among many other fast-growing startups, and his new book, The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture, hits the shelves October 2nd.

I urge you to check it out, but until then, please enjoy this interview!

Want to hear another podcast with someone who wears many different hats? — Listen to my conversation with actor, filmmaker, artist, musician, and entrepreneur Joseph Gordon-Levitt! (Stream below or right-click here to download):

This podcast is brought to you by FreshBooks. FreshBooks is the #1 cloud bookkeeping software, which is used by a ton of the start-ups I advise and many of the contractors I work with. It is the easiest way to send invoices, get paid, track your time, and track your clients.

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Scott Belsky:

Website | Twitter | Instagram | Facebook


  • Scott elaborates on how eclectic his career has been thus far — from starting Behance to becoming an investor and everything in between. [07:02]
  • Scott keeps hundreds of ideas in Evernote. Here’s why he started to organize them and what he learned in the process of breaking them down into three themes: endurance, optimization, and the final mile. [10:47]
  • What were Scott and his team trying to create and sell when they started Behance? [13:14]
  • What a venture capitalist taught Scott about salaries, heroin, and the occasional need to short-circuit one’s reward system. [15:02]
  • What recommendations does Scott have for founders, CEOs, or any kind of leader who needs to keep their team motivated through times of lean rewards? [16:58]
  • How Scott would play out best and worst case scenarios for his team. [18:28]
  • How helping a team accept the burden of uncertainty is akin to merchandising. [19:47]
  • How Scott short-circuits his own reward system, and the music and snacks he allows himself when he’s on track with his goals. [20:56]
  • Other methods for getting through tough times in the middle. [23:42]
  • What did Scott gain by looking back at old photos from five years of bootstrapping? [25:13]
  • It’s easy to get stuck in the mire of what’s not ideal about life without little reminders to keep us going, but sometimes we just have to do the job, regardless. [27:26]
  • What emotions does Scott experience by default in times of stress? [30:07]
  • What Scott discovered during times when fear would take the driver’s wheel. [31:39]
  • How Scott tries to maintain lessons learned from mistakes made under the sway of fear — even though the struggle is still quite real. [33:51]
  • How does Scott go through “what if” scenarios? [37:44]
  • Suspending disbelief as a tactic towards endurance and what Scott’s father taught him about generating hope in a New York City emergency room with 100cc of Obecalp. [40:24]
  • What increasing expectations of a current project by a hundred does to near-term doubts. [41:27]
  • The empowerment of naivete. [42:11]
  • Self-talk for founders experiencing self-doubt in their industry of choice. [43:44]
  • How do you know whether you should quit or persist? [45:18]
  • How does Scott assess conviction? [46:49]
  • Why Scott believes timing in investing is more about the present than the future. [49:20]
  • Building and perpetuating patience into a company’s culture with examples from Amazon and Alphabet/Google. [50:28]
  • What online resources does Scott reference for investing and entrepreneurship? [54:54]
  • What non-investment content is Scott reading these days? [57:52]
  • A leadership lesson from Ernest Shackleton. [58:17]
  • This part of the podcast brought to you courtesy of the truth barrel. [1:00:27]
  • What anger management wisdom can even-keeled Scott impart to me so I can have a relaxing weekend after a particularly frustrating Friday? How might this apply to someone managing a team? [1:01:11]
  • For post-conflict resolution and coping with slow progress, Scott asks what designer and thinker John Maeda would do. [1:09:48]
  • Okay. But what should I do? What will I probably do? [1:13:22]
  • Compartmentalizing uncertainty. Is a honeymoon irresponsible when your startup isn’t exactly prospering? [1:16:15]
  • Admiring people on both sides of the spectrum: from fully professional to emotionally authentic. Toward which side of the spectrum does Scott aspire? [1:17:34]
  • Sometimes the job you think you signed up for isn’t the job at all. [1:18:53]
  • Sweating and half-naked in a sauna is a perfect time to address optimization. How is resourcefulness like muscle? How did Behance’s first operations leader deal with teams who requested more resources than they really needed? [1:20:40]
  • How do I resist the urge to strain my resources? [1:23:44]
  • Real-life examples of innovative resourcefulness. [1:25:05]
  • In Jack Ma’s counterintuitive view, a startup’s lack of resources is an advantage. [1:26:58]
  • Why is initiative more important than experience in the resource-deprived startup world, and what does this look like? [1:27:14]
  • How observing initiative in others can make us take better initiative ourselves — and, as a result, better lead by example. [1:28:48]
  • What might hiring someone who has experienced adversity bring to your company’s culture? [1:30:51]
  • What the Periscope founders impressed upon Scott and why he tries to interview promising senior role candidates twice before deciding who to hire. [1:32:35]
  • After a cool-off break, we talk about everyone’s true blind spot, the context of reaction, and the role Scott once played in a Lord of the Flies style scenario. [1:34:38]
  • Scott’s experience with something called the mirror exercise and the question it prompted him to start asking others. [1:37:09]
  • What a 360 review entails, and why I recommend it to everyone even though it will probably make them feel — as I did — like a broken human being. [1:40:53]
  • Is the voice in your head you identify as you really your voice? [1:46:01]
  • Escaping the sauna to enjoy the outside world, we engage in product talk and the 30 seconds when all customers are lazy, vain, and selfish. How does not having faith in people seeing the genius of your product inform its improvement? [1:46:57]
  • How does Scott’s team stress test a product’s first design and guide its customer’s initial, first-mile experience? [1:51:18]
  • A first-mile experience going perfectly doesn’t guarantee a smooth second mile. Early adopters tend to be more forgiving than later waves of customers. [1:52:38]
  • “The Devil is in the default”: The most important decision you have to make about your product. [1:54:47]
  • Is empathy more important than passion when an entrepreneur needs to make the best choice between two or more products to launch? How does Scott recommend such a choice be made, and what does this choice mean for the team’s work that follows? [1:55:05]
  • What’s wrong with putting out a minimally viable product with the intention of making the next iteration better? For what kinds of products might this be a grudging exception? [1:56:25]
  • Are you proud of your company’s email address? Why this is often a consideration in the stages of designing a brand before a product has even been developed. [1:59:41]
  • The skills and decisions that get a leader through the beginning stages of a product launch are different from the skills necessary to keep it going and see it through acquisition and IPO — if that’s the end game. [2:04:00]
  • How one of Scott’s senior staff subconsciously worked to sabotage his own success before the company’s big pay day, and what Scott did to connect and correct the situation. [2:06:44]
  • My own experiences with “last-minute churn.” [2:08:35]
  • How do you make sure you have a successful final mile? [2:09:55]
  • Why I found it necessary to move on from what might have been the lucky success of my first book. [2:11:31]
  • What to expect from The Messy Middle, Scott’s upcoming book. [2:13:46]
  • Parting thoughts. [2:16:41]


Posted on: September 13, 2018.

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Who was interviewed? Here’s a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.