How to Be a Startup Advisor (Without Doing More Harm Than Good)

The advisory relationship is one of the most helpful and misunderstood relationships in the startup world. Here’s how to get involved if you’re a domain expert and a mensch and why to stay the fuck away from founders if you’re not.

If you’re searching how to be a startup advisor or how to become a startup advisor, this is the real job: show up with empathy, create clarity, and add leverage without hijacking the company.

Quick Summary: The 7 Rules of Great Startup Advising

• Be of service. Don’t feed your ego.
• Start with empathy for the founder journey.
• Define the advisory role clearly (scope, cadence, success criteria).
• Deliver real value (clarity, introductions, pattern recognition).
• Don’t be prescriptive. Your experience is data, not “the answer.”
• Don’t ask for compensation before you’ve proven usefulness.
• End cleanly if you can’t be helpful anymore.

What Does a Startup Advisor Do (and What They Don’t)?

This is where most people get it wrong. Advising is not “being important.” It’s being useful in a narrow lane.

If you want to become a startup advisor, start by being clear with yourself and the founder which box you’re in.

Is Advising a Fit for You?

What is the advisor’s role, and is it a fit for you?

If you’ve developed some expertise in a particular area of business building, or if you’re a current or prior operator, advising can be a great way to give back to the startup community, make new relationships, and even explore opportunities for angel investing or full-time roles.

That said, coming from a prior founder, please avoid these common mistakes and recognize that if you are taking on an advisory role your primary job is to be a mensch: your focus must be on being of service to the company.

If you’re here for ego, status, or to feel powerful, please look elsewhere. Founders don’t need another person projecting.

 Quick self-check before you advise a startup:

• Can you listen more than you talk?
• Can you say “I don’t know” without faking certainty?
• Can you respect the founder’s context even when you disagree?
• Do you have consistent time and emotional bandwidth?
• Are you willing to be judged by outcomes, not opinions?

The Advisor’s Responsibility: Be Human First

The advisor’s responsibility

Especially if you aren’t a prior founder or CEO yourself, it’s critical before entering into an advisory relationship that you familiarize yourself with and build empathy for the incredibly challenging journey an early-stage team is on.

Advisors who can’t begin with an empathic understanding of the journey will do more harm than good in an advisory role.

The responsibility here is to put care for the company and the team ahead of your own ego.

Yes, you have expertise. Yes, you deserve to be recognized and compensated for your effort. But there are thousands of people out there with expertise. What makes great advisors different from mediocre or harmful advisors is a willingness and ability to show up with empathy and humanity for the company that’s engaged you.

Your aim should be to make the short list of people the CEO or founders call when they’re feeling alone on the journey.

You get there by showing up with clear headspace and listening deeply. Seek to understand more than to be understood. A good rule: listen 3x more than you speak.

 What great startup advisors do in practice:

• They ask questions before giving opinions
• They help founders see tradeoffs and second-order effects
• They make relevant introductions and follow through
• They don’t shame founders for not taking advice
• They leave founders clearer, not smaller

Clarity: Define the Advisory Role Before You Start

The importance of clarity

Before beginning an advisory relationship, it’s critical to slow down and get to clarity on exactly what the company is looking for. Just as you would for a new job, ask for or co-create a job description and list of accountabilities for the advisory role. Work with the CEO or team to create a list of objectives and some success criteria by which you’ll know whether or not those objectives have been met.

This effort at clarity will pay major dividends as the relationship progresses. Most importantly, it will allow you to engage in the work with a shared understanding of what matters most.

After the job description is drafted and the key goals are set, assess honestly whether you’re the right person to help. If this process raises any concerns, talk through them openly with the company. Better to part ways with honesty than to fake your way through an effort that’s doomed from the offset.

Some of the people I respect most in the startup ecosystem are those willing to say ‘I don’t know enough about that, but I have a couple people in mind who can probably be helpful; let me connect you with them directly.” Aim to be that kind of advisor.

Advisory role template (copy/paste):

• Focus area:
• Primary objective (next 90 days):
• Cadence (calls / async):
• Deliverables (intros, reviews, sessions):
• Boundaries (what’s out of scope):
• Success criteria:
• Trial period length:

Clarity protects founders from wasted time and protects you from pretending you’re the right fit.

How to Manage the Advisory Relationship

How to manage the relationship

Part of the clarity setting should be determining the cadence for check-ins or working sessions with the company. If the company doesn’t suggest it, ask if there is a regular weekly, monthly, or quarterly update the company sends out that you could receive in order to stay abreast of the broader journey of the company. This will help give you context for your work.

Beyond these regular check-ins, the best advisors recognize that startup leaders, and CEO’s and founders in particular, are on an often-lonesome journey. Even as a very people-centric CEO with a lot of close friendships around me, I was surprised how many hard days I found myself wishing more people around me were checking in on me.

As a founder going through the hardest days of startup life, the days and weeks can be surprisingly slow and difficult. The loneliness can be staggering.

If a startup has asked you to advise, consider your domain expertise secondary. If you want to be true gold to the company, be the person that checks in on the people. Ask the CEO, or whomever you’re working with , how he or she is really doing. And ask a few times in a row until you get the real answer.

Be patient. Be willing to listen. Be willing to hold space without needing to override their experience with your own narrative or discomfort.

Just be there. And be there as often as you can.

Remember: this journey can get dangerously dark for some founders. Check in like it’s your job. Don’t let them disappear on your watch.

 A simple cadence that works for most startup advisors:

• 1 working session per month (45–60 min)
• 1 async update per month (short memo or email)
• 1 “human check-in” every 1–2 weeks
• Clear expectation for response time on urgent asks

Embrace the Complexity: Don’t Hand Out “The Answer”

Embrace the complexity.

So you have some experience, and some expertise. That’s just great. Really. But if you’re worth your salt you realize all teams, companies, and markets are different. What worked in your prior company may have no bearing whatsoever on what’s happening in this company today.

That doesn’t mean your experience isn’t helpful. But it’s just data. Data that gets fed into the training algorithm of this team in this company today as one thing that worked once upon a time someplace else. Nothing more.

It does not fucking mean it’s the right answer here today.

Please, advisors, read that last sentence again.

Even if you find a founder asking you for the right answer to their situation, do not offer one. Caveats are your friend here. Certainty is seductive and usually wrong. Be careful with it.

This is where sentences like ‘I’m happy to share how we thought about it and what we chose to do, but I don’t want to be prescriptive here because this is a different time and place,’ can be very helpful to both you and the company. Especially with first-time founders who are still suffering with the right answer trap.

Lean into holding awareness for the company around the complexity and around this gray zone. The best advisors will, and you should aim to be one of the greats.

 Useful phrases for startup advisors (steal these):

• “Here’s how we approached it. Different context though.”
• “Let’s map options and tradeoffs.”
• “What would make this decision obviously wrong?”
• “What’s the smallest experiment that would teach us something?”

Compensation: How to Ask (or Not Ask) as a Startup Advisor

How to ask (or not ask) for compensation

Recognize that founders are inundated with service providers, investors, and would-be advisors who are all looking for a piece of the action. Either in the form of equity asks or cash.

Once you raise a little venture capital, it seems all the crazies come out of the woodwork looking to break off their piece.

You want to be different.

In my experience, most great advisors asked for no formal structure or compensation for several months at minimum. They focus on giving value and being available to help. They try to be mensches.

If you’re providing real partnership and value, most founders will proactively offer equity compensation fairly early in the relationship. If they don’t, I won’t fault you for asking to formalize the relationship a few months in. That’s entirely appropriate. But don’t ask over your first coffee. And don’t ask before you’ve proven you actually are able to be a real partner and deliver real value.

 How startup advisor compensation usually works (high level):

• Early-stage: equity is common, cash is rarer
• Use vesting (you earn it over time)
• Start with a trial period, then formalize if it’s working

This isn’t legal advice. The point is behavior: prove value first, then formalize.

How to Become a Startup Advisor (How People Actually Get These Roles)

Most advisor roles don’t come from cold outreach. They come from reputation, visibility, and being useful in public.

 Ways to become a startup advisor:

• Pick a lane (domain + stage you’re best at)
• Share what you know (write, speak, teach)
• Help founders first (quick feedback, intros, small wins)
• Spend time in founder communities
• Ask for warm intros after you’ve delivered value

If you want to be a startup advisor, aim to be known for one specific kind of leverage: hiring, GTM, product, fundraising, partnerships, finance, etc.

When to Gracefully End Advising Relationships

When to gracefully end advising relationships

If you sign up for an advisory role with a company, take the commitment seriously. Stand by what you commit to around check-in cadences, workload, and availability.

If you find that:

• You can’t reliably meet your commitments
• The company’s values don’t match yours
• The company has evolved and you’re no longer the right fit

Then it’s time step back and have an honest, open conversation with the company. It may be time to formally end the advisory relationship. This is a place where gratitude, humility, and real authentic conversation is incredibly helpful. Be of service to the company to the very end by freeing up equity and the company’s time. And no need to end the newly found friendship.

 A clean exit script:

“I’m grateful for the trust. I don’t think I’m the right advisor for what you need next. I’d rather step out cleanly than take time I’m not earning. I’m happy to help you find a better-fit person.”

Final Thoughts: Aim to Be Great

Advisors are life-saving to early stage founders. They help bring clarity and awareness to blind-spots. But more importantly, the best ones bring real partnership and friendship during the most challenging days of startup life. Aim to be great. Your friendship is needed.

If you want a single job description: help founders make better decisions and feel less alone while doing it.

This is the second part of a two-part post. You can find part one, 'How should startups work with advisors?,' here.