A primer to startup advising

Issue 137: Looking at what advising is and if you should do it

David Hoang

Apr 2

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Happy Sunday. I was in Brooklyn this past week working, seeing friends, and two wonderful days at Kinference—the reboot of Brooklyn Beta. It's the Wednesday Adams of design conferences. This event was what so many people in design needed after nearly three years of not connecting in person.

We heard some incredible talks from wonderful keynote speakers. What's amazing is any person in the audience could have been a speaker at this. The best part was spending time and connecting with old friends and making new ones. Thank you Cameron Koczon for putting together such an awesome reunion, and reminding us why Brooklyn is truly a special place.

This week I'm sharing a bit about startup advising from the advisor lens. Though my background is in design and advising in such a capacity, I'm writing this contextually to any role.

A note about the paywall content
For free subscribers, you'll notice this is the first paywalled section. Below includes additional content on specific steps on how to get started in an advisory.

My leadership philosophy is encouraging people to work on side projects (should they want to). It helps people find a way to recharge from the day-to-day, get some variety, and learn skills they can bring back to the day job. For the past three years, my side projects have been angel investing and advising early-stage startups. With angel investing and advising, I get to work with different founders and companies in different verticals to scratch the variety itch. I've also been working at high-growth companies for the last eight years and this passion allows me to provide guidance on design, product, and company-building. I used to think advising was a bit of a farse, thinking the role was basically making suggestions to people without doing any of the work. Though there's truth to that, helping founders see around corners and share what they've seen gives them tremendously to consider their paths.

This post will focus on startup advising instead of angel investing. I wrote a blog post about angel investing from a designer's lens if you want to learn more about that. The difference between angel investing and advising is angel investors write checks and advisors don't, though angel investors might also serve as an advisor.

The role of an advisor

A startup advisor is being the Phone a Friend from Who Wants to be a Millionaire or summoning The Wolf from Pulp Fiction to fix a mess. The startup advisor is the cheat code for founders to navigate through various situations, especially when they need it most. In early-stage startups, everyone is doing multiple roles. Your Head of Design might also be your Head of Marketing and IT manager. Though not ideal, it’s the reality of early company building. In the aforementioned example, a Head of Design co-founder could bring on an advisor who is a VP of Marketing or CMO serve as an advisor. 30 minutes with an advisor with that depth of experience can help a founder get the input they need to make great decisions.

Here are a few examples of how I've helped founders I advised for:

Refer Webflow developers to design and build their company website
Review and provide feedback on the product experience
Recommend people who are great candidates for their first design hire
Suggest vendors and tools they may need to run an effective company

Adding value means being actually useful

A great advisor has deep experience and the foresight to help founders see around corners. Someone shouldn’t rush into advising until their expertise is at a place that can truly guide companies. Founders are putting a lot of their livelihoods at stake to work for the company, and there’s nothing deadlier than bad advice. In the same way, 30 minutes with a highly valuable advisor can help, executing bad advice is costly. I didn't start advising until I was a decade into my career. This isn't a requirement and an example to give you a reference point.

When I think of value add, you might have:

Subject matter expertise in an area the founder has gaps in
Useful Industry knowledge (ex: healthcare, marketplaces, etc.)
A professional network that founders would have to put a large effort getting into

High-value advisors equip startups with capabilities they don't have now.

Diligence and risks

As my friend Lauren says, "do the dilly!" In the same manner, you’re constantly closing a candidate throughout the interview process, you should be doing your diligence is something you are constantly doing, not just at the very end. The venture ecosystem is a high risk, that's why they're ventures. Risk comes in what you invest in and also what you get involved in.

Setting clear expectations

Communicating clear expectations is the key to any relationship, and the advisor/founder relationship is no different. If I advise a company, I set expectations that I never help with hiring whenever I'm in a hiring manager role due to the conflict of incentives. I also am not going to help with intros to their sales pipelines.

Don't let advising be a distracting

The majority of advisors have full-time jobs at a company. Be mindful of optics and you do not want to have this be a distraction for your day job. Perform well at your company and be clear. When I'm working full-time I do not do advising sessions during core work hours. I'll set expected time blocks to be available or meet after work.

Explore it

Advising is not something you have to do to develop your career. If you're hoping to make money from your advisory quickly, it may not be the best fit. However, if you see it as a way of mentorship, giving back, and finding a sense of fulfillment, it's a good path to consider.