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Startups: A great early-stage startup CEO needs to be a killer COO

No one likes schleps, but hackers especially dislike them. Most hackers who start startups wish they could do it by just writing some clever software, putting it on a server somewhere, and watching the money roll in—without ever having to talk to users, or negotiate with other companies, or deal with other people’s broken code. Maybe that’s possible, but I haven’t seen it.” 

— Paul Graham, Founder of  YCombinator

Paul Graham has a great article on Schlep Blindness. Schleps is a Yiddish word for tedious unpleasant tasks which as Paul rightly puts it, is what business mostly consists of. As I’ve been working on building Stocked Robotics, no words could have rung truer to my ears. Hence the title of this post, a great startup CEO needs to be a killer COO.

Let’s talk a bit about what is the difference between a CEO and a COO. Here’s a quora thread on differences between CEO and COO. I find it hard to write out a definition of these two roles, but like I usually do best when I’m learning something new, let’s learn by doing. I’ll list some common startup founder tasks, you decide whether they fall into the CEO basket or COO basket.

  1. Talking to investors to raise funding.
  2. Negotiating lease agreements for your office.
  3. Setting up bank direct debits for all your business recurring expenses.
  4. Identifying skill gaps and hiring new team members.
  5. Driving to the post office to send out vendor checks.
  6. Driving back to the office from the post office to pick up an amazon return package that you forgot to take.
  7. Working with the lawyers to iron out the terms of a pilot contract with a customer.
  8. Booking hotels for your team to travel to a customer site, then making sure they can check in and be comfortable.
  9. Building relationships with customers for sales and marketing.
  10. Driving to costco every two weeks to pick up office supplies (energy bars, soda, water, food) to make your team comfortable.
  11. Assembling IKEA furniture for every new hire.
  12. Fine tuning VAR (value added reseller) contracts.

These are my baskets:

CEO:

  1. Talking to investors to raise funding.
  2. Identifying skill gaps and hiring new team members.
  3. Building relationships with customers for sales and marketing.

COO:

Everything else.

Holy Crap, is a startup CEO more of a COO than a CEO?

Well Yes! Which echoes to what Paul Graham says in his post on schlep blindness. Let me put a disclaimer, the list I put up there has more operational tasks than leadership tasks. That’s because there is a point to all of this. As a startup CEO, you will spend a major chunk of your time doing mundane operational tasks which ensure that your business runs like a well oiled machine. The funny thing about operations is that it has a tendency to take up large amounts of time for seemingly simple tasks.

I’ve met a lot of first time founders who fall into the “avoid schleps at all costs trap”. These are people who are usually technologists first and pay no importance to the daily grind of running a business. For them, the next tweak to their algorithm or the next killer feature is what is going to keep their office lighting and plumbing running. These are the people who consider schleps as menial, worthless grunt work for lesser beings. They assume that schleps happen magically in every business and they as founders should not be bothered by such tasks. These are the fools whose startups will most likely fail hard and fast.

How do you become be a killer full stack CEO+COO startup founder?

Time management.

Time management.

Time management.

Time is the most critical resource a startup founder has and you need to start using it wisely. In a resource constrained startup environment (resources = cash, employees, equipment etc.), I like to follow what I call the bottleneck philosophy. The bottleneck philosophy dictates that in order to move the needle the most for your business, you need to focus on the biggest bottleneck your business faces today and prioritize your tasks in increasing order of bottlneck radius. (if the radius is larger, its less of a blocker, which means you can put it off for later.)

Dedicate an hour a day on weekdays and a few hours on 1 day of the weekend for operations exercises. I usually count Saturday as my operations day and try to allocate 1 hour every weekday morning before lunchtime to any pending operational tasks. If your operational task can be solved over the phone/email, save it for a car/train/bus ride as you can use your non-productive travel time.

What tools do you use to manage your time effectively?

Project Tracking

I love trello! Trello is a great way to organize your tasks into lists and cards and set checklists and due dates. Trello is how we run fundraising at Stocked Robotics and its how we manage all our administrative, legal, finance,payroll and HR related tasks. Cardinal rules of trello:

  1. As soon as a task comes to mind, add it to trello lest you forget it. Set a due date, try to set an aggressive due date and break down the task into small chunks by using a checklist. For example, If we are pitching to ABC investor, then the checklist could include steps such as reached out, 1st meeting, 2nd meeting, …, yes /  no. The due date is used to reflect the due date of the next unchecked item in the check list.
  2. Keep every task time bound. Organize priority by using the bottleneck approach.
  3. If a task becomes a blocker for your business, label it (we use the color black) and move it up the list and try to solve it immediately. Example, your landlord was unable to deduct the rent payment because of an autopay fail and threatens to evict you, you should probably send your landlord a check ASAP.

Email Scheduling

I use Evie an AI meeting scheduling assistant which is an insanely amazing tool to help cut down the time wasted in coordinating meeting times. I highly highly recommend it.

I also use Calendly especially when I’m recruiting to setup interview times with candidates. I highly recommend this tool as well.

Software Development

Jira for issue tracking and Scrum. Confluence for documentation. Bitbucket for online code repos. I highly  recommend both these tools from Atlassian. Most software engineers are very familiar with both.

Recruiting / Applicant Tracking

I love using Angellists’s track tool which is a great way to setup hiring workflow. I’ve recently started using Freshteam by Freshworks which is a pretty powerful tool for automating the recruiting process and adding candidates from multiple sources. Its also not too expensive.

When should I hire a COO?

“Great CEOs look up and out. Great COOs look down and in. It’s the parthership of their perspectives that make great companies.”

— Simon Sinek, on twitter.

There is a great article here on powerful CEO/COO relationships in silicon valley. A great COO can free up the CEO to focus on looking up and out. The CEO can focus on where the business should be a few quarters to a few years from now in order to grow into unchartered domains and take the next big leap in the business’ evolution. A great COO has the ability to look deep and down to understand how a business can improve its current operations and ready its internal machinery for future challenges.

Hiring a COO too early may not be a good thing as it is my firm belief that every startup CEO should learn the job of a COO as it reveals critical insights required to run his or her business. As your company grows, and you feel that COO responsibilities hinder your ability as the CEO to deliver value to the business, find a great COO and be best friends with him or her. It is proven that effective teamwork between a CEO and a COO can lead to tremendous success and growth for a company.

Which COO do you admire the most?

I absolutely love and admire Dave Grow‘s work. He is President & COO of Lucidchart and shares amazing pearls of wisdom on linkedin. BTW, we use lucidchart and lucidpress for pretty much everything.

Last piece of advice

Don’t ignore the mechanics of your business as its critical to building and growing your business. We all love the dynamics (fundraising, sales, giving talks at conferences), but its very important in the early days to build a well oiled machine. Get to know every little mundane detail of your business because someday that knowledge is going to help you make critical decisions that make or break your business. It will make you a more self-reliant founder, which is very important in the early days. If you’re successful and grow your team you may not have to do it on a day-to-day basis, but having the knowledge and skill set to do it sets you apart from the herd and no-one will be able to take you for a fool. They say ideas are dime a dozen, execution is key.

Published in Entrepreneurship

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