Using Constraints To Fuel Your Best Work Ever w/ Scott Belsky

Scott is one of those guests where I couldn’t possibly do justice to their resume – so apologies in advance to Scott, but here’s the short version: He’s currently the Executive Chairmen of the professional referral platform Prefer, was the founder of Behance, the creative portfolio platform that I’m sure many of you use, VP at Adobe, and author of the bestselling book “Making Ideas Happen.” I’m leaving out a ton – such as his time at Goldman Sachs, Benchmark, and as an early investor in Pinterest, Uber, and Periscope among others – but you get  the idea – incredibly accomplished entrepreneur and passionate advocate for creativity.

This episode is overflowing with nuggets but one common thread I’d like to highlight is self-awareness. You’ll hear this come up again and again – Scott is so smart that he actually outsmarts himself by recognizing his imperfections and weak spots and setting up systems that correct them, surrounding himself with people who fill those gaps, and so forth. Although rarely discussed – its a fairly subtle concept that’s often drowned out by more straightforward ones – self-awareness is a massively important attribute and I love how Scott talks about it.

Today on the podcast,

  • He has an amazing term called “the messy middle,” which essentially refers to all the stuff between the start of a company and the flashy exit or spectacular failure – basically, the stuff that actually MATTERS yet is vastly under-represented in the headlines and discussions about business
  • He is also militant about the critical importance of, well, doing shit – of focusing on execution over plans or ideas. You’ve heard me talk about this many times but I am going to keep bringing it up because it’s a massive blind spot for so many creators
  • We also riff on the value of focus and prioritizing, another common weak point for creators and entrepreneurs who are full of ideas but often have trouble sticking with one to the point that they’re able to really see it through to completion – he’s got a very cool way of visually mapping out all your projects and using that as a lens that will instantly show you where your focus is, isn’t, or should be


Stop working for agencies that work for agencies that work for agencies that work for headhunters who work for agencies. Start working for yourself. Take the reins of your own career.

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Some Questions I Ask:

  • What are you working on right now? [1:08]
  • Take us before 2006 when you were building Behance when you were still at Goldman. [5:30]
  • What are some of the near death experiences that you went through with Behance? [10:00]
  • How important is access and transparency for a creator to have with their audience? [13:43]
  • Was it intentional or an aspiration of yours to helping others get shit done? [17:05]
  • How should a creator measure their day to day? [22:10]
  • What roles do you see yourself in on the creative versus the sober monitor? [26:00]
  • What should individual creators do if they don’t have a team around them? [27:47]
  • What are some of the violations that you see that we tell ourselves that perpetuate our biggest challenges? [31:06]
  • Talk about the psychology of successful creative. [37:31]
  • One of Tim Ferriss’ hacks for getting shit done. [42:30]
  • What are some of the things that we’d be surprised to learn about you? [45:00]
  • What was it like going from being your own boss to transitioning to working for Adobe after they acquired Behance? [51:55]
  • What does it look like for individual creators to go from being a scrappy creator to moving into a bigger team? [57:00]
  • Recap your story of investing. [1:00:00]
  • Is it fair to say that you are over-indexing on people and products in your investing forays? [1:04:46]
  • How important is design thinking and growth mindset and how do you think about it? [1:10:40]
  • What are some of the tools you use? [1:12:20]
  • How important to you are habits and what are some of yours? [1:13:20]
  • What’s the role of diversity and inclusion for building teams and products? [1:15:00]
  • What’s next? [1:18:12]

In This Episode, You Will Learn:

  • How Scott is trying to bring service providers with clients through referrals with his new business, Prefer. [1:15]
  • Scott has found success in looking at ways technology hurts rather than helps people and then trying to invert it with Prefer, and also Behance. [4:00]
  • Scott started Behance to “organize the creative world” and give his creative friends a way to take the reigns on their own career through paper products, online task management application and 99U conference, which is in its 9th year this year. [6:00]
  • Why you shouldn’t necessarily listen to what people think they want. [8:00]
  • How struggle and nearly shutting down gave Behance resourcefulness, which was more valuable than having resources. [11:10]
  • The importance of transparency and loyalty. [12:47]
  • The greatest competitive advantage in business is self-awareness. [14:10]
  • “Everything that irritates us about others is a window into our soul.” – Carl Jung [15:00]
  • Scott’s thoughts on the benefits of disagreement and discussing your views in the workplace. [15:30]
  • My thoughts on the ideal balance between planning vs doing. [17:30]
  • The creative community could stand to have fewer ideas and more execution on the ones they’ve already got. [18:25]
  • Herb Kelleher, founder of Southwest Airlines has a saying “I have a strategic plan. It’s called doing things.” [18:48]
  • Why it’s important to share progress with your team. [19:15]
  • Scott’s energy line exercise for deciding how much energy to allocate to each project- this works for individuals, teams and is a good indicator of priority misalignment when deadlines are missed. [22:50]
  • What happens when you hire based on the “would I want to have a beer with this person” test? [25:39]
  • What could happen if you are an “incrementalist” without accountability built into your creative workflow? [26:15]
  • Why creatives might be compromising their natural creative tendencies by working alone. [29:00]
  • How you’ll benefit from sharing your work before it’s ready. [30:30]
  • Why you should be seeking constraints as a creative. [32:45]
  • How to market yourself. [33:25]
  • There are competitors in the creative world; let the competition can push you like Noah Kalina did. [34:10]
  • Even if you have a great long term vision, you still need a set of short term awards. You can hack your own reward system. [39:00]
  • Got kids? Scott thinks they might make you *more* productive, even though you have less time. [47:10]
  • The role of struggle in success for Scott, as well as high school friend and now pop star, Rachel Platten. [47:40]
  • Scott helped Adobe build their mobile platforms and loved the ease of scaling and moving quickly with such a big team. [54:04]
  • If you stick with a labor of love long enough, it will pay off. Every time. Don’t sacrifice them for a bigger paycheck. [58:35]
  • How Scott stumbled into investing, one product and person at a time. [1:01:01]
  • Was your decision to transition from a partner investor to a venture investor at Benchmark a result of choosing a paycheck over passion? [1:06:20]
  • The pressures of navigating what society tells you to do vs. what feels right. Be willing to be misunderstood for long periods of time. [1:07:20]
  • Scott’s favorite tools: Slack, Wunderlist, Evernote. [1:12:37]
  • How ideas are like fine wine… [1:13:00]
  • Why diversity is the antidote to groupthink and will grow ideas at the edge of reason. [1:15:17]
  • Scott’s quest to glamorize the “messy middle”. [1:19:20]


This podcast is brought to you by CreativeLive. CreativeLive is the world’s largest hub for online creative education in photo/videoart/designmusic/audiocraft/makermoney/life and the ability to make a living in any of those disciplines. They are high quality, highly curated classes taught by the world’s top experts — Pulitzer, Oscar, Grammy Award winners, New York Times best selling authors and the best entrepreneurs of our times.

Ted Livingston