I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
Awkward silence made me $30,000
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Hey Reader, Imagine getting paid for being awkward. When the financial crisis hit in early 2009, my freelance clients dropped off and all of my work dried up. I was left with just one client who then offered me a full-time job. There was only one problem: I was 18 years old and had no idea how to negotiate a salary. I asked friends and family, read a book on negotiation, and picked up a few tips. One tip was to let the employer speak first. When they name a salary, don’t immediately accept or decline—respond thoughtfully and keep negotiating. On the drive to lunch with Ken, the COO, I was thinking about what salary I wanted. $45,000 would be good. $50,000 would be amazing. Midway through our lunch, Ken said, “We’d love for you to join the team at $50,000 per year. Does that work?” I wanted to shout “Yes!” and immediately accept. But right as Ken started talking, I took a bite of my bagel sandwich. Too big of a bite. I was raised with good manners, so there was no way I was going to talk with my mouth full. I just kept chewing. And chewing. And chewing. The more I silently chewed that dense bagel, the more Ken seemed to grow uncomfortable. He broke the awkward silence: “Or we could make it $60,000.” I finally swallowed, smiled, and said, “$60,000 will work just fine. Let’s talk about the rest of the comp package.” I stayed at that company for nearly three years. So enduring that moment of awkwardness earned me nearly $30,000 more than the salary I would have happily accepted. Most people aren’t willing to ask for the full market value of their skills because they’re afraid of the discomfort of potential rejection. That would have been my reaction to the $50,000 offer had it not been for my mom’s strict manners and that lucky bite of my sandwich. — If you enjoyed this, I go a lot more into my early career story and how I progressed from day job to working for myself and eventually building Kit in my upcoming book, The Ladders of Wealth. The book releases in March of 2027, but if you pre-order the hardcover now, I'll send you info on how to get the full ebook in October and the audiobook in November (for free), so you can read it early. Thanks for your support! PODCAST$300M+ Founder: What Nobody Tells You Before Selling Your BusinessShould you sell your business or build it to own forever? Ankur Nagpal sold Teachable for $250 million and Carry for $76 million. I bootstrapped Kit and turned down a $200 million offer from Spotify. We walked two very different paths, and talked about the differences, but a lot of what we cover applies whether or not you ever sell anything. We get into:
Watch or listen to episode » VIDEOShopify CEO: Most Businesses Are Using AI WrongShane Parrish sat down with Shopify CEO Tobi Lütke for a very dense and nerdy interview—in the best way. It’s fun to listen to two brilliant minds go deep. Among many topics, they cover:
They also touch on the critical skills you’ll need in the AI age. Have a great week! —Nathan |
Nathan Barry
I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
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