Do You Need a Mentor?

For whatever reason, I'm not very good at having a mentor. I don't know exactly why — maybe it's because I have strong opinions or it seems like I'm not the most receptive to other people’s ideas, even though I like to think I am. I’ve never had a professional relationship with someone who has effectively said, “Come  here, son, let me take you under my wing.” Given that each business is so nuanced — and marketplaces like The Hub are essentially four-dimensional puzzles — I don’t know if it would be useful, quite frankly, to sit at someone’s knee and listen to them as they dole out advice from on high.

But I have found a lot of advice from people who have been through what I’m going through. They may never have positioned themselves as my mentor overtly, but they have given me nudges along the way.

The most successful of these kinds of people are those that are closer to my age. We can really meet each other at a one-to-one level when it comes to the state of each other’s lives, entrepreneurship, and the state of my company. This matters because when I think of people who are conventionally mentors, I think of people who are quite a bit older, and who have really lived some life. They might certainly have some wisdom, in the case of very tech-heavy entrepreneurship, the work I do often disrupts a lot of what other people know and love and cherish. I need someone to meet me at my level.

There are two such people who have been instrumental in my entrepreneurship journey. One is Chris Lavergne, the founder of Thought Catalog, who started his company when he was 20. When I met him he was just a little older and a little wiser, and has been through a lot of this stuff that I'd gone through. He’s given me a lot of helpful advice, as well as stern criticism, both of which have been helpful, and I’ve paid him for his time and insight along the way. Another is Julia, whom I cold-emailed after watching her in a YouTube recording of a panel. At the time, she was living in Bali, so we video chatted and then she became a formal consultant that I paid. We met on a weekly basis for a year or two, and those meetings were very helpful. She has been through a lot, knows startups, has incredible instincts and is one of the sharpest minds I know.

No matter whose advice you ultimately take, it’s difficult to find the right person. I find it funny when I see posts on LinkedIn where people say outright that they’re seeking a mentor like it’s a job posting. That’s the wrong way to go about it because mentorship, and advice-giving at large, is a very subtle, human thing. In order for the relationship to work, you have to really get close to someone and feel that you would be okay with turning into them if you took their advice. It's not as easy as simply meeting someone on the internet or having one meeting with someone in your industry and saying, bingo, you're my mentor. 

You do, however, need to find advice from somewhere. Pretty early on, I realized that The Hub was quickly becoming a personification of me, which means the company was quite objectively good at the things that I was good at, and pretty bad at other things like organizational and executive functioning, as  well as legal and accounting. Because of this, I realized that I either needed to become a lot better at those things very quickly, or hire someone, partner with someone, or learn from someone who could help. 

It is easier for me to sign off on the idea that you should build a board or a group of advisors very quickly, because these people can offer an amalgam of the varying opinions you and your company need. You can take what resonates with you from different people at different times in different ways, and sort of build your own mentorship service through this board, as opposed to relying on and perhaps vehemently disagreeing with one person who has very steadfast beliefs.

I created a board not because someone told me to, but because I wanted to. And I have to say, after my first board meeting, I was like, “Why didn't I do this sooner?” It was less about the advice I got right out of the gate, because it takes time for a board to understand the ins and outs of your company to really be able to provide tailored advice. I was, however, floored by my emotional reaction to looking around the proverbial (IE, Zoom) room seeing people, all of whom I really respect, and knowing that they'd be in the weeds with me.

This is important because one trait that distinguishes mentors and advisors from everyone else who gives you advice is that they really make it their business to understand the full picture, and to give you advice with context. This is distinct from the way a lot of people give me advice: They'll sort of fly by and off-handedly say I shouldn’t do x or y without knowing 16 other pieces of my company’s history and current workings. You don't want to be disrespectful and tell them that they don’t understand, or that you’re not going to take their advice, but when someone doesn't understand all the little things that are connected, it can be rightfully difficult to trust that their insight is what’s best. 

But in the case of a board, these are people who do know. We have two-hour board meetings, during which I can really explain the nuances of what I'm grappling with. Over time, my board has come to understand my company almost as well as I do, so when they give me advice, they're smart enough and they have enough context that I'm ready to listen to this. I know they’re not just some smart person flying by and saying something out the car window. 

If you can, seek out the wisdom of crowds rather than the definitive judgment of any one person. In my case, that’s maybe 25 percent Chris, 25 percent Julia, and about 5 percent from ten other people whose insight I've added all together and taken pieces from.I get the best thinking of all of them, as opposed to okay thinking from one of them. Not only does it help me take the advice more readily, but I’ve found it’s often sounder and more solid advice in the long run. Because while you do not know all of the answers you will need on your journey, you can work with other people who will help you figure it out.