Rookie founder mistakes

after founding and selling a handful of companies i’m qualified to share a few ways founders (including myself) waste time, money, and effort.

Monday meetings

weekly standup meetings are a great way to maintain momentum, but Monday is the worst day to do it. thanks to the federal government (statutory holidays) you’ll lose 10+ of them annually, not to mention countless other no-shows by team members due to 3 day vacations and “sick” days.

think of each meeting as a cycle, or a round in your chamber. you want all 52 rounds per year.

having patience

regular managers at regular companies may be able to afford the “marathon, not a sprint” ethos, but startups cannot. letting team members repeatedly slip on timelines will create a lax culture of non shipping. one of my portfolio companies deploys 5-10x per day, the other just 3-4x per month. the only difference is that i founded the former and acquired the latter.

one way to increase urgency is to start breaking things yourself. push untested changes directly to master, upload a sub-par design asset in a blog post, and unsubscribe from crutch subscription services. as a bonus, these tactics will also reveal who takes pride in their work.

recruiting rainmakers

this especially plagues founders with funding, either from investors or customers. they’ll decide “i need a killer sales person,” then go looking for a high performing rep from a household brand. but the larger company acquisition strategy is thanks to their system, not their people. a simple analog is McDonald’s, where team members are frequently low IQ yet produce delicious burgers.

if you hire from a large company, get ready to become their b*tch. they will spend 3 months telling you what tools and people they need to succeed. they are incapable of making their own decks, sending their own cold emails, or qualifying leads.

podcasts

when 2 dudes sit on a couch and share “battle stories,” you are not learning. you are mentally masturbating. do not listen to podcasts. read books.

delegating

high leverage roles attract 2 types of people: hard workers, and grifters. it’s easy to spot the latter because they attempt to delegate everything. these people love to say stuff like “my head of X” or “my therapist.” but good founders have a vision, which by definition cannot be assigned.

only delegate the implementation of your vision. if you don’t have a vision, get a job.

strong titles

a lot of cash-strapped startups grant C-Suite designations in lieu of compensation, rationalizing that even if the company fails, each team member’s prestigious title will help in acquiring future roles. but this is not a free exchange. thanks to our zones of competence, one day you’ll need to inject someone new, “above” your early hire, and there will be no room on the org chart.

the same goes with “Director.” at best call people Lead ___ or Senior ____. it’s your company and you do not need to explain yourself with a word salad when someone is no longer the best you can afford. i first voiced this concern 13 years ago.

reserved keywords

programming languages have words that cannot be used as variables or function names, for example if or end. in leadership a few examples include ASAP and #1 Priority. startups have dozens of priorities and everything should be ASAP.

using these words reduces their meaning to zero, which reduces your influence to zero.

publishing strategy

i’m a long time supporter of the Build In Public movement whereby founders share wins, losses, and embarrassing bug fixes to build connections and help other founders. but there is a big difference in sharing “what” vs sharing “how.”

in the past i made the mistake of outlining exactly how we acquired customers, how we built some piece of tech. then after the upvote dopamine wore off a competitor would emerge, sometimes copy-pasting our homepage word for word.

it takes tremendous effort to align yourself with customers and tap into the collective consciousness. do not provide CliffsNotes unless you’ve made your nut, are arrogant, or both.

taking advice

interweaving most of my opinions is an even stronger one to not give or take advice. if this post was interpreted as such, i apologize.