Pencil Problems

Conversations on getting started, and finishing.

About the show

Kent Fenwick (@kentf) and Nick Shim (@nim342) talk about their side projects, their day jobs, technology, the future, philosophy, 90s action movies, and much much more.

Pencil Problems on social media


  • Response: Consumer Centric Car Buying App

    May 31st, 2021  |  4 mins 15 secs
    agile, feedback, idea, mvp, pitching ideas, prototyping, startups

    Nick responds to Kent's idea

  • Episode 48: Pitch: Consumer Centric Car Buying App

    May 30th, 2021  |  3 mins 11 secs
    agile, feedback, idea, mvp, pitching ideas, prototyping, startups

    Kent pitches an idea for an app that puts the consumer in the driver seat when buying or leasing a car (pun is absolutely intended).

  • Episode 47: Season 2 Premiere: Let The Past Die

    January 14th, 2020  |  1 hr 34 mins
    books, side projects

    In this Season 2 Premier, Kent and Nick talk about what is here, what was and what is to come.

  • Episode 46: On to the next one

    January 10th, 2020  |  27 secs

    This isn't an episode it's just a teaser bruh, lots of space things and other planets in this one.

  • Episode 45: Getting the Book Published and It's a Business Not a Side Project. Goals for 2019.

    January 9th, 2019  |  1 hr 7 mins
    goals, side-projects

    Nick and Kent talk about their goals for 2019 and how a motivational video from Arnold has changed both of them in meaningful ways.

  • Episode 44: Nick's Book is Done, Finishing off Details, Setting Goals for 2019

    January 2nd, 2019  |  1 hr 51 mins
    books, business, finishing

    Nick's Book is done, like done done. Kent and Nick talk about that and what's next. Kent is worried Able Cells isn't a business but gets over it.

  • 43: A new app idea, and practical tips for finding your dream job

    December 12th, 2018  |  1 hr 26 mins
    app ideas, imposter syndrome, jobs

    In this episode Kent talks about how LinkedIn is really good if you are looking for a job. Kent talks about being open to a bunch of different opportunities and an exercise for finding the right job for you. Meanwhile, Nick has a great idea for an app, and is suffering from imposter syndrome again when it comes to be being an authority in educational gaming for kids.

  • Kent's new career, imposter syndrome v3, dating vs. marrying companies, wolves vs. dogs, building your public persona

    December 5th, 2018  |  57 mins 29 secs
    blogging, careers, meta, tech

    In this episode Kent and Nick talk about Kent's career change, building your public persona as a resume or a portfolio, marrying companies vs. dating them, the difference between being a wolf and a dog and so much more.

  • Episode 41: Essays, SEO, Project Updates, The New Rap, The Coddling Of The American Mind and more

    November 26th, 2018  |  1 hr 6 mins
    books, project update, seo, writing

    Nick and Kent talk about the new rap these days, The Coddling Of The American Mind and how we might be messing up a generation of kids, Nick talks about essays and how his book is nearly done. Kent talks Able Cells and SEO.

  • Episode 40: Screen time, Project Update, and Ramblings of a Dystopian Future

    November 4th, 2018  |  1 hr 23 mins
    books, e-commerce, ketones, nootropics, selling, side-projects, writing

    As part of a long overdue project update, we talk about: Screen time in our household, procrastination, and holding too much inventory.

  • Episode 39: Tales from the gig economy

    October 1st, 2018  |  1 hr 26 mins

    Nick and Kent talk about how software and hardware is empowering the gig economy and blowing the doors off traditional industries like lead generation for businesses.

  • Episode 38: Life at a VC Backed Startup

    August 31st, 2018  |  1 hr 39 mins
    airbnb, silicon valley, startup, tech, tilt, vc

    Today Nick picks Kent's brain about his time at Tilt and life at a VC backed startup in Silicon Valley.

    Tilt allowed users to pool funds for objectives in a simple, social, and frictionless way online. At it's zenith it was valued at almost a billion dollars and has since been acquired by Airbnb.

  • Episode 37: Starting an e-commerce store. Deep dive + Tips & Tricks.

    August 21st, 2018  |  1 hr 44 mins
    dropshipping, e-commerce, facebook ads, google ads, marketing, revenue, shopify, side hustle

    Kent got into the Mission this week, and Nick has some questions. Most of the episode centers around the article Kent wrote about how to start an e-commerce store that doesn't dropship. It goes into the weeds around starting a business, finding and pricing products, Google vs. Facebook marketing and more. Nick also confronts Kent on the question of whether this was all an elaborate piece of content marketing

  • Episode 36: The Other Side of "Hey I have an app idea!"

    August 10th, 2018  |  1 hr 39 mins
    app, builder, consulting, craft, diy, estimation

    If you make stuff I'm sure you've been approached about an idea for app or website or video or movie. We talk through our thought process and considerations when taking on other people's projects.

  • Episode 35: Feedback From My Editor

    August 2nd, 2018  |  49 mins 43 secs
    blog, book, editing, publishing, writing

    Nick gets his writing edited by Michelle Brown! They discuss how this could translate into a book. She goes over bigger on-going themes, framing devices, structure, language. It's a fun listen for anyone who has been following along with my blog or for anyone who writes!

    Michelle's book, Safe Words:

  • Episode 34: How much would you pay for Google?

    July 23rd, 2018  |  1 hr 23 mins
    advertising, freemium, google, payment, payments

    Kent and Nick talk about paying for software vs. ad based payment models. They discuss how much they would pay for services like Google, and Facebook and speculate on what the future of these payment models look like.