Pencil Problems

Pencil Problems
Conversations on getting started, and finishing.

47: Season 2 Premiere: Let The Past Die
Jan 14 • 94 min
In this Season 2 Premier, Kent and Nick talk about what is here, what was and what is to come.
46: On to the next one
Jan 10 • 0 min
We stole the summary style from Rick and Morty bruh, it's a good show if you give it a chance. We are coming back but only the shadow knows when… Probably next week… But maybe never…. But next week, most likely.
45: Getting the Book Published and It’s a Business Not a Side Project. Goals for 2019.
Jan 9, 2019 • 67 min
Description Nick's book will be published. Kent decides to stop packing boxes. And Pencil Problems will become a media conglomerate, all in 356 days. Things we talked about Arnold YouTube video Ryan Holiday - Getting advice from mentors Kitchen…
44: Nick’s Book is Done, Finishing off Details, Setting Goals for 2019
Jan 2, 2019 • 111 min
Nick's Book is Done and he's actually holding it during this episode. This calls for a celebration! But the celebration quickly moves into what is next for the book and where all of this can go in 2019 and beyond. Kent is still worried that Able Cells…
43: A new app idea, and practical tips for finding your dream job
Dec 12, 2018 • 86 min
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,…
Kent’s new career, imposter syndrome v3, dating vs. marrying companies, wolves vs. dogs, building your public persona
Dec 5, 2018 • 57 min
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.
41: Essays, SEO, Project Updates, The New Rap, The Coddling Of The American Mind and more
Nov 26, 2018 • 66 min
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.
40: Screen time, Project Update, and Ramblings of a Dystopian Future
Nov 4, 2018 • 83 min
As part of a long overdue project update, we talk about: Screen time in our household, procrastination, and holding too much inventory.
39: Tales from the gig economy
Oct 1, 2018 • 86 min
Nick and Kent take a different approach on the gig economy and talk about how software, not just hardware is making it possible to crowdsource information in new and interesting ways. Nick argues that it's all about incentives, and Kent and his Dad…
38: Life at a VC Backed Startup
Aug 31, 2018 • 99 min
Today Nick picks Kent's brain about his time at Tilt and life at a VC backed startup in the 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…
37: Starting an e-commerce store. Deep dive + Tips & Tricks.
Aug 21, 2018 • 104 min
How To Start an E-commerce Store That Doesn't Dropship
36: The Other Side of “Hey I have an app idea!”
Aug 10, 2018 • 99 min
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.
35: Feedback From My Editor
Aug 2, 2018 • 49 min
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…
34: How much would you pay for Google?
Jul 23, 2018 • 83 min
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.
33: Project Update + Goals + WWDC
Jun 24, 2018 • 53 min
Nick is back from Apple's worldwide developer conference (WWDC) and answers Kent's questions about it. Before that Nick and Kent talk about their progress towards the goals, they set a few weeks ago for their side projects. Nick is doing well, Kent isn't.
32: The Dip
Jun 6, 2018 • 90 min
We hit a dip in our projects! Kent's e-commerce store, Nick's book project, even the podcast. It's starting to feel like work and not like fun. We talk through it all and we hope you can relate!
31: Running an e-commerce store, cash flow, debt and financing, buying products, managing suppliers, calculating margins and more… A deep retail dive.
May 28, 2018 • 58 min
Kent recently appeared as a guest on This Commerce Life, a podcast about all things retail, and gets to ask Phil and Kenny, two industry veterans a ton of questions about Able Cells. They cover inventory, managing suppliers, cash flow, margins, debt and…
30: Is Google sentient? How do we build side projects in the age of strong AI? Plus some WWDC predictions.
May 21, 2018 • 87 min
Nick and Kent discuss the Google Assistant demo where an AI places a call and books a reservation. Is this software sentient? No. And how does this shape ambition when building side projects? Are certain industries dead? Plus some WWDC predictions.
29: Products we love | Fahrenheit Coffee
May 13, 2018 • 48 min
Description: Experimenting with a new episode type, Nick chats with Sameer - owner of Fahrenheit coffee. Incredible coffee, amazing dude. This episode is about passion, about craft, and about relationships. It’ll also really make you want to drink coffee!…
28: Let’s Jam | A Social Podcasting App
May 8, 2018 • 93 min
Kent and Nick chat about an app idea: A social podcasting app. Really interesting idea and lots of different directions it can go. Let's see where this goes!
27: Product vs. Marketing
Apr 30, 2018 • 111 min
Nick and Kent give their perspective on the age old debate between product and marketing. Where does product end and marketing begin, what should product people know about marketing? What should good marketers know about the product? How can you apply all…
26: Family-Work Balance
Apr 19, 2018 • 78 min
Kent and Nick have a conversation around balancing Work, Family and Side Projects.
25: Q&A - Productivity Tools, outsourcing tech, letting someone go.
Apr 13, 2018 • 65 min
We open with some project updates (, followed by some Q&A from fans (I can't believe people still listen to this!). 00:00 Project Updates 17:00 Productivity Tools 30:00 Does Kent own 300 domain names? 33:00 Does…
24: How morals and ethics affects startups, building ethics into your side project, and deleting Facebook
Apr 2, 2018 • 73 min
Nick asks Kent if he plans to delete Facebook, this leads to a discussion about Facebook's recent drama, how ethics and morals play into business, and how you can build good ethics into your side project or company. Q&A episode coming soon, send in your…
23: Hero worship, self-doubt and winning
Mar 26, 2018 • 108 min
Kent and Nick talk about Hero Worship and Self-Doubt. They ruminate about when/if they'd go all in on something and the secret to winning at side projects. Bonus Parent Corner content at the very end. Enjoy!
22: Pros and Cons of Building Side Projects with a Team or Going Solo
Mar 18, 2018 • 104 min
Nick and Kent talk about the pros and cons of starting side projects with a team or going solo. They also answer a hypothetical question about what would they tell their 25-year-old selves.
21: Filming a Kickstarter Video, How to Deal with a Drop in Shopify Orders - Project Update #3
Mar 7, 2018 • 35 min
In this episode, Kent and Nick give a quick product update on the book and Able Cells. Kent is worried that he went 2 days without an order and wants to rebuild Shopify. Nick is working on storyboards for his likely Kickstarter video. Kent records a…
20: Lessons Learned Pitching Sponsors
Mar 3, 2018 • 56 min
In this episode, Nick and Kent talk about how it went pitching the podcast to a few potential sponsors. Like a good math problem, they work out a solution for what sponsorship could look like going forward. Remember to send any feedback or questions to…
19: Getting Sponsors
Feb 22, 2018 • 77 min
In this episode, Nick and I talk about the vision of Pencil Problems going forward and how we would try and pitch it to potential sponsors. We also kick-off Parent Corner around 1:03. Enjoy
18: Book Club
Feb 16, 2018 • 127 min
Nick and Kent talk about the books they love and how they shape their actions, worldview, and their kids' future. Full of tangential goodness.
17: State of our Unions
Feb 2, 2018 • 61 min
Kent and Nick talk about whether Jack should kick Donald off Twitter, then roll right into an extended project update with a snazzy new transition sound effect. Kent rails about Able Cells, while Nick tries to figure out a broader context for his book…
16: Self-driving roulette
Jan 25, 2018 • 101 min
Kent and Nick talk about their side projects, answer listener questions about email marketing, and health and fitness, the difference between tools and products, Nick tells us about CES and Kent and Nick make a bitcoin bet about self driving cars in 2030.
15: Intellectual Summer Camp
Jan 12, 2018 • 111 min
Kent and Nick get their first listener feedback, they talk about their time at The DGP, why grad school is like intellectual summer camp, advice for people thinking about grad school, academic politics, doing research, intellectual freedom and end with a…
14: A time for selling
Jan 4, 2018 • 117 min
Nick and Kent talk about the future of pencil problems, their goals for the podcast in 2018, whether or not Nick should dabble in the black hat world of e-commerce, personal goals, las vegas buffets, zig ziglar, kent's crypto corner and so much more. This…
13: Crypto
Dec 14, 2017 • 130 min
Kent and Nick talk about Bitcoin, Etherium, Litecoin, tokens, and their gambling problems
12: OK Google, open the pod bay doors
Dec 8, 2017 • 103 min
Nick and Kent talk about their worst episode yet, then move right into the war of the living room, Google Home, vs. Echo vs. Homepod vs. Sonos, they talk about the internet of things, the role of voice, and stay tuned for a bitcoin price prediction.
11: Imposter Syndrome
Dec 2, 2017 • 101 min
Nick and Kent talk about the imposter syndrome, confidence, the Dreyfus model of skills acquisition, pragmatic thinking and learning, cooking, achieving mastery, and Kent puts out a reward to our 5 listeners
10: What Would Jay-Z Do?
Nov 26, 2017 • 107 min
Nick and Kent talk about Disney World, Pandora, Pixar, Jay-Z, ambition, Jay-Z level ambition, good being the enemy of great, the secret, reality distortion fields, the fact that we made it to 10 episodes and then back to Jay-Z.
9: Pivot
Nov 15, 2017 • 109 min
Kent and Nick talk about pivoting a company or business, Microsoft and their failure to pivot, Google and their dozens of pivots, Apple's big pivot, Facebook's huge pivot gamble, VR, AR, becoming a God in Second Life, and when you know it's time to…
8: Programming System 1
Nov 9, 2017 • 96 min
Kent and Nick talk about Cargo Cults, making data driven decisions, system 1 and system 2, intuition, doctors, AI and that's about it.
7: Rationing your Wonderbread
Nov 3, 2017 • 82 min
Nick and Kent talk about company culture, the good and bad of backchanneling, the right way to give feedback, and finding a balance between the light and the dark.
6: Welcome to the Rock
Oct 25, 2017 • 75 min
Kent and Nick talk about piracy, publishing on Medium, making money on Medium, Prometheus, The Rock, and how not to get a book published.
5: Waiting for that Casper money
Oct 20, 2017 • 106 min
Kent and Nick talk about ambition curves, what they would do if they got paid to do the podcast, what they really want to do with their lives, and talked more about potential productive pencil problems.
4: Productive epiphanies
Oct 11, 2017 • 99 min
Show Notes Trello Asana 10 Years of Getting Things Done OmniFocus Chapter markers Coming soon.
3: Searching for breadth vs. depth
Oct 4, 2017 • 104 min
Nick and Kent talk about bluetooth headsets, breadth vs. depth, the problem with drop shippers, how grad school is basically paid summer camp, and how Nick is looking for an agent.
2: That time I went to Taylor
Sep 27, 2017 • 87 min
Nick and Kent talk about the difference between main street and big retail and how that applies to apps. Kent rails on the kids these days, and Nick shares an awkward story involving vulgar lyrics and his mother.
1: Everyone has a price…
Sep 20, 2017 • 80 min
In the first episode of Pencil Problems, Nick and Kent talk about why this podcast nearly didn't happen, what projects they are currently working on, what ketones are, how they pick projects and decide which ones to stick with, how parenting is…