Alisa Cohn on Prenups for Startup Founders, How to Reinvent Your Career, the Importance of “Pre-Mortems,” and the Three Selves (#539)

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“If you like these problems, let’s solve these problems. These are the problems you’ve chosen for yourself.”

Alisa Cohn

Alisa Cohn (@AlisaCohn) is one of the most prominent startup coaches in the world. She has advised founders and executives at Venmo, Etsy, DraftKings, Wirecutter, Mack Weldon, InVision, Tory Burch, and others. She has also coached CEOs and C-suite executives at enterprises such as Dell, Hitachi, Sony, Google, Microsoft, Bloomberg, The New York Times Company, and Calvin Klein.

She is the author of From Start-Up to Grown-Up, a guidebook for entrepreneurs on the leadership journey from founder to CEO, and host of the From Start-Up to Grown-Up Podcast. Her articles have appeared in Harvard Business Review, Forbes, and Inc. magazines, and she has been featured as an expert on Bloomberg TV, the BBC World News, and in The New York Times. A recovering CPA and one-time startup CFO and strategy consultant, she is now an angel investor and advisory board member. Outside of work, she is a (very) amateur rap artist and an investor in Broadway shows, two of which have won Tony Awards.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

Alisa Cohn on Prenups for Startup Founders, How to Reinvent Your Career, the Importance of “Pre-Mortems,” and the Three Selves (#539)

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with someone else who understands the value of difficult feedback? Listen in on my conversation with Instagram co-founder Kevin Systrom, in which we discuss approaches to getting honest feedback from the conflict-avoidant, how to take honest feedback non-defensively, how to give honest feedback without fear, what a 360 interview can teach us, how disallowing a seven on a one-to-10 scale when soliciting feedback prompts honesty, and much more.

#369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users


  • Connect with Alisa Cohn:

Website | Twitter | Facebook | Instagram | LinkedIn


  • Alisa fills us in on her background, the journey, and the catalyst that opened her up to coaching as a career possibility. [06:51]
  • How trying to backtrack at a crossroads revealed Alisa’s superpower, and what she learned about unexpected qualifications sometimes outshining impressive resume highlights and postgraduate degrees in the eyes of a potential employer. [17:11]
  • What was it about coach Cheryl Richardson that appealed to Alisa when she was still trying to figure out her own career trajectory? [22:12]
  • How does Alisa’s approach to dispensing advice empower the person asking for it? [23:56]
  • When it was clear the door to Alisa’s Goldman Sachs opportunity had closed, how did she fare at the startup she’d chosen instead? [25:56]
  • How Alisa finally found her footing as a “real” coach after reluctantly bouncing back and forth across the country to act as a startup’s temporary CFO and home office GM. [28:22]
  • Alisa shares what happened on her San Diego pilgrimage to meet legendary coach Marshall Goldsmith, how she was able to make the connection through a cold email pitch, and what she brought to the table that made her a valuable part of his coaching team. [33:23]
  • On the devastating power of 360 feedback. [40:16]
  • When 360 feedback prompted an unexpectedly terrifying response from a COO in India. [43:50]
  • The challenges of addressing concerns and fixing problems with 360 feedback while maintaining anonymity when working with a small team. [46:21]
  • What have I found valuable about 360 feedback in my own experience, and what have I changed as a result of enduring it? [50:09]
  • Premortem versus postmortem in the 360 feedback process. [52:34]
  • Alisa’s suggestions for ensuring a meeting is productive. [55:11]
  • To offsite or not to offsite? [58:29]
  • Clarifying why it makes no sense for an organization to fret over small expenses when it doesn’t prioritize a need for meetings to be productive. [1:04:28]
  • How Alisa suggests communicating with someone who doesn’t improve upon feedback you’ve already given them (perhaps multiple times). [1:08:27]
  • When no amount of feedback does the trick and the only recourse is to fire the repeat offender, how does that conversation go? [1:11:32]
  • Books or resources for making these types of conversations go more smoothly. [1:14:00]
  • An example of why holding off on having a difficult conversation with an underperforming team member doesn’t do either party any favors. [1:17:01]
  • The “three words that you think about when you think about me” exercise and how it’s meant to demonstrate the way we see ourselves versus how others see us. [1:19:53]
  • Reframing through failures and accepting that obstacles aren’t merely obstructions along a given path, but the path itself. [1:25:50]
  • How Alisa gears her self-talk to favor motivation over demoralization. [1:28:21]
  • The three selfs: self-awareness, self-compassion, and self-talk, and the bridge of self-compassion that takes you to them. [1:33:11]
  • Where does “I will be okay no matter what” come in? [1:35:28]
  • Just because life’s circumstances may have taken a turn for the better doesn’t mean the anxiety from which you’ve always suffered will follow suit. [1:37:02]
  • How did From Start-Up to Grown-Up come to be, and why did it take 10-and-a-half-years of work? [1:39:00]
  • What got Alisa over the hurdle of procrastination to actually finish the book? What changed? [1:42:12]
  • On the three sections of From Start-Up to Grown-UpManaging YouManaging Them, and Managing the Business. [1:46:36]
  • The prenup and checklist questions for managing the “marriage” of business partnership. [1:49:10]
  • What does Alisa hope readers will take away from From Start-Up to Grown-Up? [1:53:11]
  • Leadership is an unnatural act. [1:55:43]
  • Resources for people who want to learn more about the economics and ecosystem of Broadway. [1:56:20]
  • What would Alisa’s two-sided billboard say? [1:59:05]
  • Parting thoughts. [1:59:52]
  • Alisa gives a rundown of the scripts she’ll share here, the people who will make the best use of them, and the circumstances for which they’re most ideal. [2:02:11]
  • Scripts for quick, positive feedback (including one to use when someone is struggling), and how to make sure you integrate their use into your daily routine. [2:05:50]
  • A developmental feedback script to use with an employee who is junior to you. [2:08:03]
  • A developmental feedback script to use with an employee who plays a managerial role. [2:08:50]
  • A script for having a difficult feedback conversation (aka constructive criticism) with an employee. [2:09:50]
  • A couple of scripts for having difficult feedback conversations with employees when the first one’s been used but the situation hasn’t improved (and you’re not ready to fire them — yet). [2:12:02]
  • The firing conversation script. [2:15:33]
  • Scripts for soliciting more feedback from your managers and bosses. [2:17:47]
  • A script you can use to either set or reset expectations for your employees. [2:21:03]
  • Questions you can ask your employees so that you can have a deeper conversation about work in your one-on-one. [2:22:23]
  • A script for introducing the idea of career coaching, and proactive questions to ask about future goals and expectations. [2:23:23]
  • A script for telling someone you’re bringing in a manager on top of them. [2:25:30]
  • Simple networking scripts, resources, and suggestions. [2:27:54]
  • An email script you can use to reconnect with an old friend or colleague. [2:31:42]


“Leadership is an unnatural act.”
— Alisa Cohn

“I don’t know what it’s like to be with me. I only know what it’s like to be me.”
— Alisa Cohn

“If you’re lucky, you pick your problems.”
— Alisa Cohn

“When you talk down to yourself, when you criticize yourself, especially harshly, you’re actually burning up a lot of calories that you could have used to actually solve the problem. You’re not your most resourceful, you’re not your most creative and best self when you’re beating yourself up.”
— Alisa Cohn

“Believe in yourself, and then act like it.”
— Alisa Cohn

“Problems, problems everywhere.”
— Alisa Cohn

“If you like these problems, let’s solve these problems. These are the problems you’ve chosen for yourself.”
— Alisa Cohn


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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7 Replies to “Alisa Cohn on Prenups for Startup Founders, How to Reinvent Your Career, the Importance of “Pre-Mortems,” and the Three Selves (#539)”

  1. Hi Tim

    Prenups are based upon the concept that after 20 years of marriage you have some tangible assets …

    I took the esoteric eastern minimalistic life a little too far and made the bread line look like the skyline.

    Between immigration and debt we are making inroads to a decent living now .

    Should I be worried now my Life partner will elope with the mailman now?


  2. This comment doesn’t relate to this episode, which I’ve not yet listened to. It’s a podcast guest recommendation: Jonathan Meiburg, longtime member of the the Austin based band Shearwater and author of the recently published book, “A Most Remarkable Creature,” which was just long listed for a 2022 Andrew Carnegie Medal for Excellence. The remarkable creature being referred to in the book title is the striated caracara, found in the Falkland Islands, but, as the Dallas Morning News said in a review, “Calling this a bird book is like calling ‘Moby Dick’ a whaling manual.” I think a conversation with him would make for a great show. And, if you haven’t read the book, I think that for sure you’ll enjoy it.

  3. I just listened to this episode and was struck by how easily and openly Alisa shared how she works, it was very generous of her to do so. “Leadership is an unnatural act’ will be forever in my memory.

    The conversation about Tim’s 360 feedback was priceless. It’s so very common for people to recoil, at first. As Alisa said, it can be tough to see criticism in black and white print. Even when it’s mild, it can disrupt very accomplished, smart, people. Talking about it specifically and from personal experience is so helpful for people to hear.

    I was listening to this episode while in my car and upon arriving at my destination, I stayed in the car in a dank parking garage so I could listen to the very end.

    Well done!

  4. you are an expert on your intention. Everyone else is expert on your impact. And also People observe your communication and what you do. Pre-mortem. Assume failure. What contributed to it

  5. Pre-mortems and Broadway in one episode. I feel like Alisa and Jen Waldman (Coach to many Broadway actors who’s also a big proponent of pre-mortems) could be best friends! Great Ep, Tim.

  6. She was amazing, but Tim, you weirdly used more curse words with her during this interview — definitely more than you ever have with the men you’ve interviewed. Take a look. Something to think about.