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When I Grow Up.......

80's and 90's kids may remember Malcom in the Middle. It's the story of a boy genius growing up in a middle-class, blue collar family (before Bryan Cranston started cooking meth). In one of the most thematic episodes, Malcom took a career aptitude test, hoping to find clarity on college, career, and beyond. Unfortunately for our young protagonist, the tests came back troubling - you can do anything! While some people might be ecstatic to have a world full of possibility, the existence of a non-answer thrust Malcolm into an existential crisis - a feeling some Founders may be familiar with. Before $10m ARR, you are probably the best at just about everything in the company. You'll have the highest close rate, secure renewals and upgrades at a solid clip, marketing material you build will generate the highest engagement, and you'll be the best at discussing your product and market with investors and partners At some point, you need to pass some functions off. Unless you're a technical founder, product is the first to go, making a hire for a PM, VP Engineering, or proper CTO.

We're left with Marketing, Sales, and Customer Success, and a question set: 1. What order do you hire in? 2. Do you hire Director, VP, or CxO level? 3. How do you spend your time? 4. How "hands on" should you be with your new org leads?


Clearly a lot of deep second-order questions depending on model, market, funding, etc....are you differentiating based on product or brand, or both? How nascent is your market? Do you have some secret sauce in the model that is defensible? How long is your runway, and do you have a high probability of bridging to the next stage of your company?


Lets go all Dr. Phil for a second, and ignore that for a minute. For this article, lets call back to Malcolm's crisis, and think of some questions that help manage burnout, and fill the proper skill gaps. Principle 1: You do you Assuming you're pretty good at everything, what can you see yourself doing for the next year or so? Do you get more amped about closing a new deal, or meeting an old client looking to expand? When you finish a QBR or onsite visit, does your mind first drift to product+process, or are you thinking of ways to monetize? Do you get more excited looking at adoption dashboards, or watching pipeline develop? Answering these questions can help determine where you need solid individual contributors, and where you need an executive or senior manager.


Principle 2: What are you really good at?


What is your comparative advantage compared to other founders? Do you ship amazing code, or write user stories that give your firm a 6-12 month technical advantage? Can you close "stretch" deals that are above your product-market-fit? Are you an amazing recruiter and fundraiser? Do you get amped being a keynote, or having 1,000 people engage your content on LinkedIn or Medium? Early stage, your skillset is a competitive advantage when leveraged. Find people that are better then you at other things, and focus on your strength. Kinda like Free-Trade for team building.


Principle 3: What bores you to death? Simple on this one. What do you hate doing? Support? Client checkins? Appointment setting? Writing documentation? Find people that love what you hate, and don't burnout.


Principle 4: Dance when the music calls. ....or not. to reference Principle 1, you do you.

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