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!

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#336: Scott Belsky — How to Conquer the Messy Middle

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):

#312: Joseph Gordon-Levitt — Actor, Filmmaker, and Entrepreneur

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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]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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25 Replies to “Scott Belsky — How to Conquer the Messy Middle (#336)”

  1. Going pop-up crazy are we, Tim?

    I click away one, cause I’m already subscribed to all, and it obscures the content.

    Then one slides in from the left.

    Which I click away.

    Then the first one pops up again, which I have to click on again…

    Oh my… pop-up heaven! ;-p

    Ps. You know I love you, or you should, cause I’ve been reading your stuff, off- and online for a looooong time already, but pop-ups I don’t…

    Now I’ll just get back to the content, shall I? 😉

  2. Hi Tim, have you ever tried getting Kapil Gupta on your show? He has mentioned you before, so I know that you have some sort of relationship 🙂

  3. Hey there, man. So this is gonna sound like quite a long shot but I figured I’d give it a go because hey.. why not. I’m currently a 4th year student at the Maharishi University of Management in Fairfield, Iowa. You might’ve already heard of the place but if not, it’s where Jim Carrey gave his graduation speech a few years back. Consciousness-based education, meditation, all that stuff. Really unique place with some seriously impressive people living among us here.

    Anyways, to get to the point, I’m currently taking a course called growing a business and we are covering the stock market right now and the finer points of long term investment, how to assess the viability of a successful company, etc. Your books have played a pivotal role in my life over the past few years and I figured, again on a total long shot here, I’d reach out to see if you might have 20-30 minutes to skype in to our class and talk about your experience as an angel investor, what you look for before investing, and anything else you would deem relevant.

    Now, I know that time is money (especially for a man in your position), and you’ve probably got a million other things to deal with on a daily basis, but I’m asking anyways. I can’t personally offer you anything for your time other than my sincerest gratitude and appreciation so if that’s a deal breaker right there alone I’m willing to accept that, I have no expectations that you’ll even see this but you know.. what is there to lose. Whether this reaches you or not, and whether this interests you or not, I hope this message finds you well and that you’re having a good day, man. Thanks for all you do for others, you’ve brought a lot of good to this world and have every right to be proud of yourself (not that you need me to tell you that).

    Anyways, there’s my proposition. All the best to you, man

    – Danny Flynn

  4. Tim,

    Thank you and Scott Belsky for helping me see some light at the end of the start up tunnel. My last seven years has included a significant TBI, battles with addiction, depression, weight, my first marriage, having two kiddos, trying to transition from wild man to family man, three moves (one international), lay offs for both my wife and I (one literally a month after we just bought a new house), being a stay home dad and starting a my first business. Specifically the last two weeks have been especially low, for example, only got out of bed to drop kids off at school and help put them too bed. My “Start Up To Do” list only has about three weeks of focused work left until I can hang my open sign so to speak. It is so frustrating to be so close to something, to have all the info and abilities to do well yet see yourself unable to barely move at times. Having a pre-TBI frame of reference of being a 10+ year martial arts, college graduate, 15 years as an engineer, rich and motivated life seeing oneself flounder is heart breaking. Man depression, TBI and mental health in general is no joke.

    The bits Scott spoke of around endurance, boot strapping, levels of ambiguity, along with the crash that comes once the newness of startup wares off. Maybe best of all is telling oneself DO YOUR FUCKING JOB 😉

    Thanks again for all the info, tools and wisdom you’ve provided since episode 1 and for staying humble.


  5. Really enjoy your content. Just wondering when someone is going to interview you???

    Waiting for it…

    I binge listen Tim podcasts like normal people binge watch Netflix

    Maybe it’s out there and I’m just a hermit.

  6. Podcasts seem to be the new thing in the world of information. Do you have any thoughts on why this is becoming the case?


    Alexander Viking

  7. Hey Tim! Honestly trying to contact you any way I can at the minute haha. Reading through 4 hour work week at the minute and I said I’d make a stab at contacting you. I also genuinely wanted to ask you where you played hurling in Ireland during your short stay, and if you have plans to come back in the future?

    All the best! Un abrazo fuerte

  8. G’day Tim

    Here’s something that’s changing the way I look at anger. It’s from a hand out we were given at my mens’ group, where we discuss a different theme each week eg anger, sadness, joy, honouring, shame etc. Something may or may not resonate with you – I hope you (and your followers) at least enjoy the read!



    Anger, by Dick Silberman, Mankind Project

    Men feel anger for a variety of reasons, some obvious and some elusive. I might feel angry when I’m in danger, or when I feel disrespected by another man. In fact, I used to go to anger pretty often.

    Someone did something and it “made me angry.” I have read that another person can’t really “make” me angry, and that I can to respond to others without feeling or expressing anger, if though this might be my default—or even justified in the circumstances.

    Why, then, did I feel angry when I could just as easily have been sad or afraid in the same situations?

    Anger can cover up other feelings—feelings that we as men may feel less comfortable expressing. It seems that in our culture it’s “OK” for a “real man” to get angry and stick up for himself; but what man wants to admit he is feeling afraid or sad? It doesn’t sound nearly as macho, does it?

    It took some work on my part, but I came to realize that for me, almost all of my anger was covering fear. I eventually got to the point that as soon as I felt any hint of anger I asked myself, “So, what am I afraid of here?” And with a bit of practice I came up with answers.

    Here is an example: When my wife did such and such, I was afraid that her criticism was too accurate, which meant I wasn’t an ideal husband, which meant she might not like me anymore and I’d be alone again, and…damn it, I got mad instead of feeling all those bummer things.

    Once I learned to be aware of it and call myself on it, something magical happened: I stopped being angry. It was as if a switch had been thrown and I really came to understand what it meant to own my shadow.

    I’ve learned to use my anger in a healthy way, to let it out in a controlled, positive way.

    I’ve also learned that, at times, I use anger to make myself feel safer, and to hide other feelings, like sadness, fear and shame. Now, I don’t go to anger to cover other feelings, I instead I work on them in my igroup.

  9. Hello Tim, i am en entrepreneur and would like some suggestions on books to read for ideas in getting ones business to the next level; and how to invest in the business to bring about growth. Thank you love your podcasts.

  10. So even tough the wording is somewhat lame and generic, I have to start off by saying I am a big fan!! Working in a huge IT company for the past 7 years, I had paradoxically left the world of podcasts unexplored for too long and am only starting to catch up. Even though I have to say so far your show is my number one addiction in that area.

    I have just very recently quit my job and am now on a quest for self exploration which I shall be combining with travelling (south east Asia is making this affordable for me) and also initiating my training as a yoga instructor, which is a whole different story altogether.

    Anyhow, it is such a blessing to hear people from all backgrounds and all genres talk so openly about their life’s and failures, successes. I am often awestruck by the beauty of them sharing their vulnerability and it makes me feel less alone and more convinced that I need to be doing something different with my life and the quitting of such a secure job was the right decision for me personally.

    What strikes me, especially after listening to so many stories of enterpreneurs, is how to manage to organise oneself. I have a huge urge to learn and read more, yet, being an obliger personality and a somewhat twisted, creative mind, I seem to fail to make the time and structure in order to find the right medium and stay on it for long enough so I can actually bring my thoughts to paper and in appropriate form.

    I seem like a little puppy that is shown new toys constantly. I jump from one to the other and forget where I actually had left of, which leads

    To a lot of unfinished business and very little satisfaction and actual output.

    Listening to one of your podcasts with Scott belsky, I find the time as I am I a train ride which gives me time To listen, reflect and take notes. However my personal challenge mentally is still with the previous episode, in which Brandon Stanton mentioned how he read 100 pages non fiction (!!!!) on a daily basis. Something I am so awestruck with, I can’t even put in words how many years I’ve tried to read even 10

    Minutes on a daily basis and still managed to fuck that up. *sorrry about the f word there, but sometimes it’s just right*

    So my very long question would be, how do your hosts, including yourself manage your time for these ‘everyday goals’, let alone bigger ones? I am sure there is as many answers

    And tools of organisation to this as character traits (answer is in the question?!), but if you could help my ‘sack of flees’ brain on that one, I’d be eternally grateful. And hey, if the yoga proofs to be successful, I throw in a bunch of free lessons ^^

    Thanks for everything, in case this email remains unanswered, which I would not blame you for, understanding some tiny bits of the workload you must face.

    Keep on rocking it!! And small PS, I’d be great to hear even more female entrepreneurs on your show. As a women I can only underline how few role models one is presented with in everyday life and media that are famous for their wits instead of … you get the idea.

    Again, thanks and all the very best.


  11. I couldn’t be more grateful for the service you provide and the positivity you project. Even though we’ve never met, you’re one of the five people I hang out with the most because I’ve spent so much time with your podcasts. You’re awesome, I appreciate you, and thank you so much!

    -Reporting Live From The Messy Middle

  12. This was a great episode. I very much appreciated how you discussed your experience trying to volunteer with a nonprofit.

    I would like to suggest that you consider interviewing non profit entrepreneurs. For example, someone like Robin Steinberg, who has a proven track record of starting and building successful non profits (maybe in biased because I’m a lawyer). She would have a lot of experience to share in terms of leadership and growth.

    Anyway, just a suggestion!

  13. Yet another gem Tim. Thank you for doing what you do! As someone in the comments said below, we have never met before but I feel like I hang out the most with you and your brethren Shane Parrish, the most! I alternate between the two of you every week on my weekly long runs. At the end of 2 hours of run, I cannot ask for better mental/emotional health.

    What I loved in this episode:

    1) Carly Commando – found her beautiful “Everyday” track, about 10 years ago and listen to it every time I find a need for concentration. Couldn’t help but cheer out loud during my run when I heard Scott mention that as one of his tracks while writing.

    2) Obecalp!!!

  14. Tim, very curious how you approached the nonprofit after asking advice from Scott re: how to handle. How did that shake out?

    I submit below my clarifying questions and thoughts below on how I might hope to handle. I submit only b/c you asked for advice and b/c I’ve learned so much from you that I wanted to take a chance at *maybe* helping you in this situation.

    Firstly, I would ask, how do you think your mentor Ben Franklin would handle this situation? I would surmise that he would bring a cool-headedness and even keeled temperament toward next steps

    Secondly, clarifying Q’s for you to better understand how to approach your next steps:

    · Even though you feel like your time has been wasted and trust has been broken, how would you rate the upside of continuing forth? Does this have a likely life changing positive impact of 8, 9, or 10? If so, a bump in the road for that upside seems worthwhile

    · Would you be ok walking away from this group entirely? Or do you think that at age 80 looking back you’ll wish you attempted to reconcile?

    Given the context that I have from your podcast, my proposed response is below:

    Dear nonprofit representative name,

    I realize that coordinating the volume of volunteers and their specific demands must be a difficult and almost thankless job given everyone’s high expectations. You face the unenviable task of balancing each volunteer’s desired schedule with the overall program schedule to ensure everything simply gets done. Given this, I must commend you partaking to solve this logistical nightmare as part of our collective brooder desire to help.

    That said, I must still express my sadness in seeing my proposed schedule (which I am unable to accommodate) given the upfront agreement that I thought we had of when I could participate.

    I would humbly ask that you please honor our original proposed schedule that we had agreed upon previously, if you can do so I would be eternally grateful and look forward to this endeavor which I believe will be a life changing positive event for both me and for all involved.

    If this cannot be accommodated I will be forced to withdraw from all participation whatsoever due to prior engagements. This greatly saddens me as I believe I’ll look back at age 80 and wish this could’ve worked as we all intended in our upfront agreement. Your ability to move the puzzle pieces around to rectify things would certainly not be lost on me and I sincerely hope both of our 80 year old selves will book on all that we accomplished together after this moment

    Thank you

  15. Tim, I bet I know why you were angry over the non-profit incident. Your dominant need state was threatened. I’m sure you’re familiar with the six human needs as commonly discussed by Tony Robbins. Every time you’re triggered to the point ruminating for a weekend, I bet you can trace it to that.

  16. Hey Tim, been listening for a year or so and taking your advice as I can into my coaching and special education career. One thing hit home with me in your interview with Scott where you described you inner talk and that you seem to expect the good things that happen to happen because that was your job and then you get caught celebrating less. Then you described how that inner tough talk comes out when talking to other for my example it’s my players. How did you or are you working on this. I am going to look into the reviews and the mental toughness for athletes but looking for some help whether like you said help me to help other or have other help me.

  17. Hey Tim – Just wanted to say thank you for all the inspiration over the past few years. The more I grow up – the more I realize how much I have yet to learn, and yet to experience. Your books, teachings, and guidance have helped ground me in truth, in world that is losing touch of itself. Thank you, Dillon D (NYC)