Startup Mentors — How Do You Filter Out The Good, The Bad And The Ugly?

In light of the recent brouhaha over the actions of a particular European investor who had a habit of attaching himself to accelerators as a ‘mentor’, it seems an appropriate time to do a quick rundown on the kinds of things entrepreneurs need to look for in genuine potential mentor to them and their companies. Because, in case you have been hiding under a rock, there a lot of new ’mentors’ flooding towards technology startups, and it would be good if everyone had a clear idea of how this relationship should play out.

I asked on Twitter and on Facebook for some fast feedback on this and got what I think is a pretty representative list of ideas around what due diligence you should do when looking for a mentor for your startup. (Apologies if I don’t name-check everyone who contributed, but to give you a flavour…)

Matt Clifford of Entrepreneur First, thinks there are three main issues.

Firstly, he says, “you can’t get a (good) mentor by asking someone to be your mentor.”

He says a lot of young entrepreneurs think they need a mentor, so they assume that they should go around asking for on. But, the “best mentor relationships seem to develop organically. The entrepreneur has a series of interactions with someone and after a while both sides realise they’re getting value from the conversations and – de facto – the person has become a mentor.”

Secondly, “asking good questions is the key to being a good mentee (but is hard work).” A question like “What should I do?” is way too vague. You’ll get the most out of mentors when you ask them real, important, very specific questions that provide a lot of context, says Clifford.

Thirdly, first-time founders usually “want the wrong mentors.” First timers picking a “celebrity mentor” or one who is far, far ahead, is often a bad idea and they are much better off with someone “two to five years ahead of them on a similar journey” says Clifford.

Most of the day-to-day challenges founders face are highly stage-specific, he says. Is this the right person to help you get your first 1,000 users, for instance? “Hire more sales people” is not really an answer, and someone who’s been in that same place very recently is usually better.

Startups can of course help themselves by clubbing together and sharing information on mentors. Perhaps write a notional “mentor spec”?

But still, the basic questions apply: what they’ve done or achieved besides mentoring and advising.

Entrepreneur Ian Broom tells me: “I get mentors to agree a contract, like a staff member, and set expectations. Especially if you’re offering equity, it’s crucial the mentor vests like everyone else.”

James Bromley of Swiftkey adds that you should ask for references. And are they “ground level practical”? Also check if the mentor is a frequent ‘conference bore’, rather than actually working.

Matthias Metternich of says you should check out the prospective mentor’s network and whether they’d be open to making relevant introductions to others. He also advises getting mentors who fulfil functional roles and who can go deep. “We have separate mentors for mobile, bus dev, branding, marketing, hiring, etc”

Mentors who are still “doers” are more valuable.

And keep them in the loop: “No one can mentor well without understanding what’s up – it’s a two-way street,” points out Metternich .

Russell Buckley, formerly of Admob now partner of Ballpark Ventures, says you shouldn’t over-pay mentors and Non-Execs, and wrote about here.

He agrees that vesting options along with other staff members means “you can fire people who don’t deliver to the stated expectations.”

“I’m also encouraging some of the companies I work with to set OKRs or KPIs (depending on the tools they use) for their Board and advisors. Not a popular idea with many Directors, but I would like to see it as normal. After all, most investor/directors sell themselves as adding value prior to the investment, so why not hold them accountable?”

Use tools to check out a mentor’s credentials and investments such as Companies House /

And looking through their AngelList, LinkedIn and Twitter / social profiles etc is an obvious move but sometimes forgotten.

Eileen Tso Burbidge of Passion Capital says if the mentor has written catchy blog posts that can even qualify as usefulness as a mentor.

Then there is Jason Lemkin’s 2.5x rule which is: “After 2 1/2 meetings, after 2 1/2 intros to VCs or potential VP hires, after 2 1/2 times they “help” … you need to “pay” or they go away. Until then, you don’t have to pay. And many people if they are interested in you will make a few connections and help for free. 2-3 times.”

The simplest way to pay mentors he says is to give them some stock options and if you can, let them invest in your seed, “A and B rounds IF they want to”. But, don’t connect the two. “The first is a (for now) unquantifiable “payment” for helping. The second is a “thank you”. Don’t confuse the two, but try to do both.”

Michael Geer, COO of Dream Industries in Moscow, emailed be a few choice thoughts. “Mentorship takes the perfect timing of the team looking for mentorship and the mentor actually having the bandwidth and desire to mentor. That is much harder to get when just one side reaches out.” He says it comes together roost naturally when his mentorships have “started from accelerators or classes I’ve taught.”

He notes a drawback: many teams are either not ready to listen or not at the right stage to actually action some mentors’ most valuable advice when one side or the other reaches out. “Of course, when the timing is right, both sides learn and gain a lot.”

But how do you avoid bad mentors?

Matt Clifford says: “This is a very effective way of avoiding bad mentors, especially financially motivated ones: they just won’t last out the repeated interactions.”

In other words, bad mentors don’t burnt out, they fade away…