Part 3: Company-Internals Mistakes

Everything started out with good intentions… then you can’t get funding, reviews dip on Glassdoor – or worse – there’s a lawsuit. How did things get there?! Most likely, one small misstep at a time.

As you know, there's a lot going on. The goal of this list is not to add more to your plate, but to start getting you aware of things to think about, in the short - and long-term.

Business Operations

Product Focus

Mentors and Advisors

Congratulations! You’ve been accepted into an accelerator and/or just brought on an advisor (or two). Here are some DOs and DONTs :) 

Company Culture

Companies are made of people who aren’t perfect; there’s no perfect company culture that works for everyone – my company included. Where are you doing well? What can be improved?

[Biggest mistake] #1 mistake I see founders make is not communicating enough, with each other – and the rest of the company. Everyone can improve on their communication, myself included. To make sure there are no surprises for anyone, strive to overcommunicate! Even if there are “only” two of you (!).



Do you have an onboarding doc, sharing not just the company mission and goals, but also whom to go to for what, where everything is, along with the goals for the first week? 


Hiring is hard! The Biggest mistake that I see founders make (understandably because of budget constraints and hiring for an early-stage start-up), is crafting a job description that reads either like a kitchen sink of technologies they’re mostly not using (but everyone else seems to be using and hiring for) – or (on the flip-side) the needs are for one person that will be doing 3 full-time roles, across departments… all for equity compensation only. 


infrastructure_cost + platform_team_cost < current_vendor_costs

where platform_team_costs can be $1M+/year for a manager to lead a team of 4-5 developers.

Data and AI Strategy

Parting Advice

There’s a story (or two) behind each of these (!); I’m always happy to meet other leaders and swap stories and lessons learned.


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