We are BACK.

We talk through how to approach a startup idea in a space you aren't in expert in, how to build momentum and make decisions fast, and the problem mindset. We also talk through how everyone was wrong about Robert Frost's The Road Not Taken and what that means for Brian's vertical farm startup. 

• The Tacklebox Method - link to discount for ITS listeners
• Founder Venn Diagram - free, in Foundations -> Founder Venn Diagram
• The Growth Mindset 
• Tom Eisenmann interview - Why Startups Fail

Jeff Sheldon is the founder of Ugmonk, a company I have an enormous amount of admiration for. It's a thoughtful, purposeful, highly effective business that creates and curates beautifully designed products. Jeff has run and grown the business slowly and sustainably (without funding), building an incredibly engaged customer base. This strong customer affinity allows him to launch products through crowdfunding campaigns without a massive marketing budget.

We talk through how he built Ugmonk, how he thinks about curation and design, and we go deep on his most recent Kickstarter campaign - a ~half million dollar raise for Analog.  

• Ugmonk
• Analog
• Tacklebox Self Serve Accelerator

The past 15 months kicked our butts. We all picked up some terrible habits, and we get a pass for it. But now it's time to dig ourselves out of the hole.

This episode goes through three questions that'll help you refocus, tactics to find your North Star, and a framework to reset your inputs. There's never been a better time to build a startup, and if you haven't got an idea or are deciding between a few - this is the place to start. 

• Spirited Away
• Tacklebox

Inertia is the tendency to not change. Everyone is on a path driven by inertia, which leads just about everyone to always repeat the same things. Which is a problem if you're starting a startup, since you need people to do something different (buy your thing).

In this episode we talk through inertia and how to build startups that leverage it vs. fight it, with cameos from Javier the Hot Air Balloon Guy, Erin Andrews, and Donald Trump. 

• SPONSOR: Bluprint + their Indiegogo campaign - the only coffee maker that cares about your entire day
• Tacklebox article: Don't Edit Your Deck, Edit Your Investors
• Article on Erin Andrews + Donald Trump on social media

Today we've got Tom Eisenmann on the pod. He's an entrepreneurship teacher at HBS and the author of the white-hot startup book "Why Startups Fail." We had a blast talking through all the mistakes startups make and the best ways to avoid them. We also talk through how to validate when you've got big up front costs, when domain experts are important (and when they're not), and how to start the gig-economy version of the private chef. 

• Why Startups Fail
• Tacklebox Cohort 28 (Apply)
• Validate Your Startup Idea in a Weekend (Webinar)
• The Mom Test
• Four Steps to the Epiphany

There’s one decision that early stage founders make that can drastically tip the tables in their favor.  This is a tactical episode, helping you push through the critical question of what customer segment to target first. We delve into a framework to help you identify and evaluate customer segments as your startup evolves. 

• Tacklebox Cohort 28 starts June 2 - apply by May 15
• Tacklebox Self-Serve no cohort, grow at your own pace

This week's ITS Classic covers whether your startup idea is any good. We talk through a failed startup Brian ran called Find Your Lobster, present a framework to ensure you choose the startup idea that best matches your skillset, and how to stay away from the dreaded Whisper Idea. 

• Byldd is a venture studio that’s democratizing software entrepreneurship.
• Tacklebox Accelerator Cohort 28 starts June 2, applications are due May 15th.

I recently asked a good investor friend of mine what he thought the most underrated but important skill for entrepreneurs in 2021 was. He responded quickly - storytelling. The amount of compelling copy a startup needs to write in 2021 is astounding - from ads to emails to socials to pitch decks - and the base rate has gotten extremely high. A startup can only be as successful as it's messaging, and that all starts with a founder's ability to tell the story of their customer and their product.

Today's ITS Classic episode talks through storytelling archetypes that'll help you write compelling copy and become a 10x better marketer.  

• Tacklebox Cohort 27 starts June 2, Apply by May 1
• Pixar's 22 Rules of Storytelling

We revisit an episode from the early days of the podcast on an operating system for founders. Not everything I say here has stuck, and not everything I do I recommend. But the bones of this podcast are rock solid. Being thoughtful about how you work and what you work on is the key for building a startup in the margins. And, everyone has more margins now. If you're one of the people who isn't going to have to commute again, this is your chance. Build an internal operating system so you maximize your output without burning out or killing your creativity.

• Tacklebox Cohort 28 (Apply by May 1, starts June 2) 
• Tacklebox Self-Serve (if you want to go through the cohort content at your own pace)

Predicting a startup will fail is like betting every number on the roulette wheel except that green double zero and then puffing out your chest when one of your numbers hits. It's just not impressive to predict that something going up against overwhelming odds won't beat those odds.

And yet.... Sometimes people build startups like horses asses. And in that case, they need to be called out.

This podcast originally aired the day Quibi launched back in April of 2020 and gave the company 18 months to survive. It didn't come close. This podcast isn't dancing on the grave of a company that failed. It's pointing out all the completely predictable and avoidable mistakes the company made so you won't make them, too. 

• Tacklebox Cohort 28 (June 2)