The advice and thinking that leads you to make important mistakes there really is no need to make:

1/ “Ask VCs for Advice When You Want Money, Money When You Want Advice”.

I don’t know who started this, but they must be smarter and more perceptive than me. I get asked for advice a lot. I get asked for money a lot. I have 60 hours a week. Please help me really know which you want. Especially the money part. I probably will pass on investing in you if I don’t know you want money. We recently did a New New in Venture event, and I asked the question of many top VCs, including David Sacks, Keith Rabois, Aileen Lee, and more. Most say the same — just send us the pitch when you are ready. We move quickly.

2/ “Just Give the VP of Sales More Time”.

This is always terrible advice. If a VP of Sales can’t improve things in one sales cycle or less, or at least just a smidge longer — they never will. And you are better off without them. This doesn’t mean the improvement has to be magical. But it does have to be there, quantitatively. In one sales cycle, or less. It’s your fault for making the wrong hire, but more time won’t fix it. More on that here.

3/ “We Can’t Afford It”.

Bear with me here. If something is accretive — you can afford it. As CEO, you need to find a way. That’s your job. If a great VP of Marketing can double your inbound leads — of course you can afford her salary. If an outbound sales team really can generate more revenue than it costs … if an event can generate more customer revenue than it costs to put on … if an engineer can build more features, that close more customer revenue than her salary … etc. etc. You can’t afford stuff that doesn’t make you money until you are relatively big. But after just $1m-$2m in ARR, you can afford everything that makes you money. Find a way. More on this here.

4/ “Let’s add a Freemium Edition.” “Let’s Add a Super Cheap Edition.”

This rarely works unless it’s truly a Top 3 corporate initiative … and even then, it’s tough. If you were going to have a successful freemium edition … you’d already have a freemium edition. It doesn’t work because freemium is rarely a go-to-market and marketing strategy. Free almost never generates enough users to be worth it. Nor does a Cheap Edition. The effort here is almost always extremely dilutive of your time and resources.

5/ “I don’t need a real VP of Marketing … Yet.”

Of course you do — if you have any sort of repeating business. Don’t hire some junior marketing person that can’t really get you more leads. Hire someone that can get it done. That can own it. That can get you more leads, more opportunities, more top-of-the-funnel stuff going. Hiring a junior person after even $20k in MRR is a waste of time. You need an owner. An owner will add more net new revenue than her salary. A non-owner won’t. So an owner is cheaper. At twice the price.



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