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Jim Hopkinson on Embracing the New, the Importance of a Side Projects, and Tips on Negotiation – Cracking Creativity Episode 34

Jim Hopkinson is an author, speaker, teacher, and, entrepreneur. Jim has worked at startups, big corporations, and for himself at In this episode, Jim talks about the lessons he learned while working at ESPN and WIRED, why side projects are important, and the best ways to negotiate your salary.

Here are three lessons you can learn from Jim:

Embrace the New

Jim has always been ahead of the curve when it comes to emerging technologies. He was a digital producer before that title even existed and he has always embraced new technology.

While at ESPN he worked on the team that was creating the ESPN phone before cell phones became a part of every day life. He helped manage the Twitter and Facebook accounts at WIRED, and helped WIRED get into podcasting.

All this isn’t to tout his accomplishments. It just shows you that embracing change can put you ahead of the curve. Don’t be stuck in your old ways. Be willing to pivot and try new things.

Importance of Side Projects

While Jim was working at WIRED he was also working on his own projects. He was podcasting on the side for five years and wrote his own eBook on salary negotiation.
These endeavors may not have paid off immediately, but when he was let got at WIRED, he had something to fall back on. Instead of scrambling to find a new job, Jim was prepared because he was doing things on the side.

Right around the time he was fired, he was also offered the chance to speak at SxSW. He has now spoken there six times. He was also able to leverage his eBook into

All of this shows you that you can’t rely on others to make your living. Jim has been let go multiple times, and each time he was able to get right back on his feet.

Research Before Taking an Employer’s Offer

When most people accept a new job, they take what’s given to them. They normally think “I should just be grateful to have a job.” Jim doesn’t think that way. If you don’t negotiate your salary, you could be missing out on thousands if not tens of thousands of dollars.

The biggest problem with most people is, they do very little research when negotiating. Here are the five places to learn about how much your job could be paying you: salary research sites, job board sites, industry research guides, your internal network, and your external network. By doing a little research, you can find out exactly what you are worth. Instead of going in blind, be prepared to ask what you’re worth.


  • Jim’s career overview
    • three careers – startups, corporations, and solopreneur
    • third employee at interactive training program
    • decided to pursue dream job, moved from Boston to Seattle doing fantasy football
    • moved on to WIRE while also doing side gigs
    • when he was laid off in 2011, he had something to fall back on
  • Steve Jobs quote: “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”
    • saw major trends in career
    • worked in different emerging technologies
    • the remote work and online learning as the future
  • what he learned at different stops
    • took the internet a while to catch up with what he was good at
    • his job title finally emerged as a producer (knowing info. in a bunch of different areas)
  • specialization vs. being jack of all trades
    • for job seekers, it is easier to be specialized in a certain area
    • his specialization early on was being a tech geek
    • struggled to find a job after graduating so he worked at Staples
    • got an interview with Spinnaker Software and used selling Dell computers to get his job
  • job at ESPN
    • didn’t want to renew lease and wanted to move to do what he loved
    • looked at things he loved to do
    • knew he needed to do something creative to get a job there
    • got an in through networking, called contact once a week
    • bluffed and said he would be in Seattle and asked for an interview
    • made excuse and made his way to Seattle
    • studied site and company

“I just knew so much about the company [ESPN] that there was no way I wasn’t going to get that job once I got that opportunity.”

  • moving from ESPN to WIRED
    • switching jobs and the affect of 9/11
    • stayed for 5 more years
    • ESPN phone team was let go while he was apart of it
    • interviewed right before trip to Africa
  • working at WIRED
    • launched Twitter/Facebook page/podcast
    • strength of brand takes you a long way
    • testing to see what works
    • was transferred from tech to publishing
    • went from working with cool tools to trying to convince people to subscribe
    • giving away freebies for subscriptions
    • disruptions in business vs. existing business models
  • Good to Great – Jim Collins and knowing when to pivot
    • Kodak and digital cameras
    • designating people to keep up to date on the industry you are in
    • being large vs. being small and agile
    • change forcing you to evaluate your place in life
    • entrepreneurs need to constantly evolve and evaluate

“How do you pivot? How do you keep disrupting yourself? And I think it has to be in your culture from the beginning to constantly act as if you’re the upstart.”

  • side business and building an audience
    • started his podcast on the side for five years for free
    • wrote ebook on negotiating salary write before he was laid off
    • within thirty deals of being laid off he went to Buenos Aires to work remotely
  • choosing the published vs unpublished route
    • weighed pros and cons
    • physical book, marketing support, etc. vs. doing all the work himself
    • nothing has compelled him enough to make another book
    • has turned to online courses instead
  • becoming the salary tutor
    • he has been on both sides of the hiring process
    • salary negotiation for job out of college
    • finding success in a “failed” negotiation
    • being prepared and doing everything you can to get a higher salary
    • pursuing another job or taking the offer
    • story of two men hired on the same day with same experience and having a $20k salary difference

Even if you do make a counter-offer and they say no, at least you’re avoiding that one word, and that one word is regret.

  • doing HR for startup
    • saw hiring process from the other side
    • immersed himself in negotiation techniques
    • most advice for negotiating deals with the minor details: handshake, resume, etc.
    • teaches social media at NYU, which allows him to take classes, so he got certified in career development

“One thing I do really great is, I look into a problem that fascinates me and do cray deep dive research and I have to share it with people in an entertain and informative way.”

  • tale of two interns
    • opening for an assistant
    • his intern Suzie getting call for job
      • didn’t negotiating when receiving it
    • intern Kenny held off when they made first offer
      • call back and verify info
      • got advice from Jim on what to do
      • told different story of living situation during interview
    • just by asking, Kenny got the highest pay for an intern in company history
  • being willing to ask
    • Amanda Palmer’s book The Art of Asking and TED talk
    • worked with woman working entry level job who negotiated up a few dollars an hour
    • asking for more sets a great precedent
    • if you do it the right way in a professional manner, it shows what you can do and makes a statement to hiring manager that you know your worth, are good at business, and are willing to have difficult conversations
    • getting discount at Banana Republic
    • you never know until you ask
    • Noah Kagan – asking 10% off at coffee shop
    • friend getting a discount for tires by fake talking to Jim
    • the worst thing that can happen is paying regular price

“If you know enough and you would like to have fun with it and get over that fear… say is there anything you an do about that, is there any flexibility in that number… it’s amazing what you can do.”

  • other keys to negotiation
    • doing research and knowing value on the market
    • there’s so much more you can do then look up your salary on Glassdoor,, etc.
    • go beyond research and have confidence
    • five keys to negotiating a higher salary
      1. salary research sites
      2. job board sites
      3. industry research guides
      4. internal network
      5. external network
    • info and research lead to confidence
  • biggest gain for client was $70k
    • got no raise for 4 years
    • researched and found she was worth $120k-$150k
    • asked for $140k HR said no
    • she was willing to leave, they called her back a few hours later
    • goes back to give 2 weeks notice, old job is then willing to concede and she turns them down
  • speaking at SxSW
    • got offer after first book came out
    • first year was book reading, second was facilitation, third was panel with moderator and speakers
    • spoke 3x at Austin and Las Vegas
    • adds credibility to his name
  • morning routine
    • checks emails and deletes things
    • water to hydrate and gym/smoothie
    • email/shower/meditation with Calm
    • gratitude journal
  • podcasts, tools, resources
  • creative people
    • Jason Zook – I Wear Your Shirt, selling his last name, Buy My Future
    • Elon Musk – starting every venture that he wants to
  • definition of creativity
    • getting podcast sponsored by WIRED
    • making podcast demo with friend
    • recording of friend talking about his phone company – they weren’t interested
    • talk about brunch place – they became interested

“What would you do if you couldn’t fail?”

“Try things as if only possible outcome is to succeed” | Salary and Negotiation Fast Class

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