The Top 5 Things Investors Can Support You With

Some hands-off investors will be turned off when you turn to them for guidance, however...

An investor who put in $5 million certainly won’t hesitate to give you their 2 cents - especially on certain topics.

Most founders screw this up because they feel like they're asking too much, or that it's not an investor's job to help them with operational decisions.

White-knuckling your growth is probably the dumbest thing a founder can do.

The smartest founders I know regularly lean on their investors for a bit of help.

How to Think About Investor Assistance

It's a pretty simple rubric:

• What are they able to help you with...
• Where your investor has more expertise / connections than you...
• That isn't going to be a huge time commitment from them (i.e. the 10-minute rule)...
• But will have a huge impact on your business's value.

If you make it easy, fast and high-value, it'll probably be a great ask - AND it'll probably get done.

The Best Things to Ask Investors For

There's a few things that commonly fit into the "you should ask for this" rubric:

1. CFO. Most startups don't have their finance function sorted out. It's a problem. But any lead investor is going to be able to reco a few CFO candidates - and who better to watch their money than someone they already know and trust?
2. CMO. 70 cents of every dollar invested by VCs goes toward marketing. The wrong hire can mean burning cash for no apparent reason.
3. Large Enterprise Customer relationships. Maybe your best investor happens to play golf with your 5 best Fortune 500 customers. Why wouldn't they want to intro? (it will be YOUR job to make them look good!)
4. Channel Partner / Distribution relationships. They're tough to find, but some dream investors can put you in front of potential large channel partners that could see you distributing 10x next year.
5. Next-Stage Investors. It's shocking butnot every investor has relationships with next-round's investors (eg. Seed -x-> Series A). But some do, and you want to warm-intro those ASAP to get a head start on next round's relationships.

When to Ask

Get the best possible minds working for you for free. Do this by asking smart questions at pitch stage.

This allows you to get the investor actively thinking that “ok, it’s not just about the money, and they are clearly open to outside advice on key decisions.”

In other words, they’re picking up what you’re putting down. At investor deck stage, ‘a penny for your thoughts’ is a great carrot to dangle if you want to incentivize a more appropriate level of investor commitment.

Big Fish Only

But beware - a 0.5% investor and a 49% investor are not created equal!

When you ask a question, expect to get a reply.

Don’t let someone’s two cents buy more influence than they’re paying for. That’s how you wind up with someone’s wayward niece walking straight out of rehab onto your board.

Remember, you’re not a supplicant. You’re not a charity, and it's the founder who ultimately makes decisions unless the board votes otherwise.

Summary

When done correctly, asking questions of investors isn’t a sign of weakness. No one has all the answers. And teams don’t always have all the spots filled for their key positions. As long as you don’t come off completely clueless, then it’s no problem to ask.

I recommend a great book for getting in the right frame of mind to turn your investor deck into an investor onboarding. It’s called Pitch Anything: An Innovative Method for Presenting, Persuading and Winning the Deal. It’s author is Oren Klaff and he comes at things from an angle we like.