Lessons and Observations on Running Startups & Small Businesses

Lessons and Observations on Running Startups & Small Businesses

The operational know-how on a business is obvious, a startup, not so much.

If you know the path of your company and product/market fit are established, hire position players, not generalists.

To poach someone, take them to a customer meeting and watch their reactions.

Non-diverse teams fail more often.

Brute force you and your team’s collision factor in your industry and ask people from it tons of questions. Get them to talk talk talk while you learn learn learn.

If you’re in the app business, know all the apps. If you’re in the banana business, know every variety of banana. Know your business and the mechanics of how it operates under a variety of conditions and flavors.

Emotions, ego, and assumptions help ruin businesses, not competitors.

If you have competitors, you need to be highly performant, optimized or heuristically awesome, and have a much higher quality of user experience to grow quickly. Think orders of magnitude better not marginally improved.

Train your employees with documentation and video screencasts consistently when they onboard. This applies to startups too.

Your company culture is shit if it matches every other place. It’s not unique, special, or worth it. I think the best company cultures make most potential candidates want to vomit and leave the room, because then they filter for grabbing the best people who really want to be there.

A VC can get by on 4X returns to his LP’s, so be cognizant.

The same dance that many founders do with VC’s is the same dance VC’s do with LP’s. They use CRM’s, talk to other VC’s about LP’s, and try to get the right intros to the right family offices and institutions.

Over-communicate customer feedback and details with the entire team by forwarding them to the entire team.

In the early days, don’t have a cancellation button, you need to find out why they’re canceling.

In sales, if the customer isn’t doing most of the talking, then you’ve probably failed. The goal is to get them to characterize their problem for more than 50% of the conversation, so you can arbitrage it.

If you’ve raised funding, don’t do things you don’t have to do…. laundry, cooking, cleaning, scheduling, or booking travel. Outsource it. There’s too many teammates and too much money relying on you to do activities that affect the balance sheet and product outcomes.

If you’ve got a company card, do the math and load balance credit cards to make the points multiply into LTV for your team, and extend the lifeline. Maximize your points.

Engineering always costs more than selling. Get out there and sell.

If your business relies on networking, then do a monthly event and invite the most epic people in your life, and tell them they can bring friends, they just have to RSVP and say who they’re bringing. Your network will multiply automagically. Make intros at this event and have fun, because you’ll be busy the other 29 days of the month.

Most VC’s are losers. Numerically objective reality.

ALWAYS NEGOTIATE! Stop being a pansy and negotiate. It’s longer runway for your company.
Paying a supplier and short on cash? Ask for no-interest financing.
Using a SAAS service? Offer to blog about, share, and speak about the app in exchange for a discount. Offer a backlink yo. The pagerank struggle is real…

Don’t waste too much time blogging.

Pay your teammates well and train them. Egg them on because they’re awesome.

If there’s an elephant in the room, kill it.

Brand and marketing don’t always correlate with substance, be willing to accept this.

Don’t waste time with doryphores, they’ll drain you.

Everyone has flaws, accept it, move on, and remember everyone including yourself is a work in progress.

The really really freaking hard part about making decisions as a leader is understanding that even the things you might not think are decisions, actually are. The most subversive reality presented to a decision maker is that the decisions you make are followed by the perceptions of others, regardless of whether or not their opinion/viewpoint matters on the issue. Balancing this is really tough.