By: Nate Bek
Talk to any startup expert about building the next Silicon Valley, and they’ll often point to one key element: a strong pipeline of seasoned advisors.
Startup advisors are trusted guides who bring wisdom and insight to the ridiculously tough journey of building a business. They offer strategic advice, share hard-earned lessons, and provide mentorship that goes far beyond simple guidance. Advisors are sounding boards for ideas, connectors to crucial networks, and steady hands in times of uncertainty. A great advisor can be a kingmaker.
For those in big tech or engineering roles outside the startup ecosystem, breaking into advisory roles can be challenging — there can be broad gaps between the networks of people who’ve spent their careers in companies that have already scaled, and those of serial entrepreneurs and startup founders.
Typically, these gaps are filled by institutional matchmakers — programs designed to connect founders with aspiring mentors.
In Seattle, Techstars served as one of those intermediaries. It brought together tech leaders, former founders, and investors. Its final “Mentor Madness” event paired 211 mentors with the 24 startups in its cohort, and nearly 350 mentors were listed on its website. No other local program operates at that scale today (although Foundations aims to help fill that void).
Techstars excelled at transforming casual introductions into lasting advisory relationships, helping a number of Seattle startups grow. The program provided structure and guidance for mentors, supported by resources like David Cohen’s Mentor Manifesto.
Now, with Techstars out of Seattle, the way startup advisors connect with founders has slowed.
The shift raises a big question: How do we continue to support the Seattle startup ecosystem with a steady flow of new advisors?
We’ve created an FAQ for big tech professionals interested in upholding the region’s robust mentor network. We gathered insights from both seasoned and emerging advisors.
Here’s what we learned:
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Advising startups offers a chance to stay at the cutting-edge while sharing valuable experience. For many, it’s about being part of the journey, helping others overcome challenges, and staying connected to the pulse of new ideas and technologies.
Advisors are rarely in it just for the money, though equity packages and cash compensation are common.
Taylor Black, a Director on Microsoft's Incubation Studio & Strategic Programs Team and former B2B SaaS founder, says he’s driven by the thrill of working with early-stage companies.
“I love the zero-to-one space, getting from idea to product-market fit and all the questions that come with it,” he says.
With experience in deep tech, consumer, and platform technologies at Microsoft, Black has guided hundreds of startups through those critical first steps. The motivation is the excitement of turning ideas into reality and solving the puzzles that come with it.
David Pitman, a former staff engineer at Google Cloud and exited founder, says advising is about giving back.
“I got a lot of great mentoring and advising when I was a founder,” he says. “Some of those people are still my mentors today.” It’s a way to pay it forward, sharing hard-earned wisdom and staying connected.
Pitman adds that advising can be a two-way street: “You can rapidly build up a lot more knowledge about, say, how the current funding environment is going.”
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Aseem Datar, vice president of next-gen computing and AI platform at Microsoft and a former Madrona Partner, says it’s important for you to find “advisor-founder fit.”
Stage: Figure out which stage of the startup’s lifecycle best fits your skills. If you’re like Black, that’s at the very early stages when the company is developing a product. But for others in big tech, it might make more sense to work with a later-stage company that found product-market fit and is looking to scale.
Value add: Determine the types of problems a founder might have, and how your unique skill set fills that gap. This could be customer intros, technical advice, supply chain support, culture and internal processes, and more.
Goals and financial situation: Some startups don’t have the cash on hand to pay you right away, or at all. Others might want to pay you and not want to give you equity for your help. The ideal situation is a mutual agreement with the founder and a genuine desire to help, which rewards a secondary bonus to you “picking up the shovel” and actually helping the startup grow.
Jim Alkove, founder of a cybersecurity startup and advisor to several others, says that you should start with determining your “why:” What do you want to achieve? And where can you offer the most value?
Black’s advice is straightforward: “Go for it, but be honest about what you’re good at. If you haven't built something from zero to one, don’t advise on that. Instead, focus on what you really know — whether that’s Kubernetes, C++, or setting up strong dev environments.”
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Becoming an advisor is much like finding a new job. Begin by building a strong network and offering your help before officially taking on an advisory role to establish your value.
Connections with venture capitalists and startup studios can increase your visibility to startups. In relationships to both founders and their investors, offer customer introductions, even for companies you don’t plan to work with long term. Also offer your expertise as a trusted third-party reference. Alkove notes that he spends a significant amount of time on quick reference checks and technology due diligence, sometimes more than on customer intros.
He adds that his portfolio of advisory roles came from three key sources:
Echomark: Had an existing relationship with the founder, a former colleague at Microsoft.
Safebase: Spent time with the team and offered help, eventually joining as advisor.
Ambit: Was introduced through his relationships with venture capitalists.
Alkove says the most important aspect is spending time with the team. Understand their culture and product to see where you fit in and jump on opportunities to help.
There are also existing programs that you can join that serve as intermediaries:
For hardware-focused startups, Amish Patel launched Conduit Venture Labs’ Fellows. Taylor Black is a fellow there, and I wrote the story for GeekWire here.
For women-led companies, Seattle-based Graham & Walker has its Catalyst program (Jen Haller and I participated as mentors in its most recent Cohort).
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When pitching yourself as an advisor, avoid positioning it as a pay-to-play network. Customer intros are important but should be done thoughtfully and with credibility. They should also be just one of many tools you offer to founders.
For Alkove, his value lies in his CISO connections. As a former executive at Salesforce, he was the buyer of cybersecurity tools, which enabled him to advise on how product pitches would be received.
“If you’re the ideal customer profile, that's valuable,” he says.
Pitman, drawing on his experience from Google Cloud and multiple startups, highlights the broad applicability of lessons learned in building from zero to one and thousands to billions.
His experiences with software, UX, and AI can help new tech companies avoid costly mistakes they have to unravel after they start rapidly growing post-Series A.
“The advantage of an advisor is having someone who can help you see ahead to the next stage of your company before you get there, basically giving a superpower to see into the future,” he says.
However, he cautions against applying big tech solutions to startups without considering their practicality. “If you can't come up with a realistic way that some small startup is going to be able to put your advice into action, it's probably not that useful for them,” he says.
Black combines his founder experience and legal background to excel in the zero-to-product-market-fit stage. He has worked in three venture studios, launching startups in deep tech, consumer tech, and platform at Microsoft. Black focuses on testing, ideation, and gathering data for product-market fit. He also uses his legal expertise to craft B2B contracts, which are crucial for refining a product and achieving product-market fit.
Programs like Conduit Venture Labs' Fellows program works with tech leaders to help hardware-focused startups avoid common pitfalls such as high burn rates, supply chain issues, and limited venture capital interest.
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When diligencing startups, start with traditional factors: market potential, team background, product viability, and investors. These metrics provide a foundation, but to achieve advisor-founder fit, Pitman looks deeper into his relationship with the founder and the practicality of their professional alignment.
“I really want to understand as rapidly as possible if I can actually give useful advice,” he says. Pitman is cautious of founders who claim everything is perfect. “If you think your startup is doing great, you either got that lottery ticket—congrats—or, like most founders, something is always going wrong.”
To test the relationship, Pitman offers a small piece of advice early on and watches how founders respond. “I want to know this is going in a productive direction and not just giving advice that goes nowhere,” he says.
But Pitman is careful not to overstep: “I’d be more concerned if a startup took my advice without seeing it as one data point among many.”
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Most enterprise professionals seek engaging and interesting opportunities outside their day job, with equity and cash often being secondary concerns—or not a concern at all. Their main motivation is to participate in something exciting beyond their regular work.
Many advisory engagements don't involve equity, especially when facilitated through platforms like incubators. Black, for example, offers startups around five one-hour sessions initially. After that, he prompts them to decide whether to formalize the relationship.
The choice between equity and cash depends on the advisor’s goals and the length of the engagement. Black advises opting for equity in long-term engagements due to its potential and crisp alignment with the startup's own fortunes. For short-term projects or one-off contributions, cash might be more practical. In early-stage startups, particularly those transitioning from zero to one, equity is often preferred over cash given the startup’s limited resources.
Equity pricing can be difficult to standardize, but resources like the Founder Institute’s FAST template provide a framework. An advisor dedicating at least 20 hours a month to an early-stage startup might expect around 1% equity.
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Best practices start with connecting deeply with the team. If you’re a tech expert, engage with the engineers. Understand their challenges. Your job is to answer questions and ask the right ones, exposing areas for growth. Think of it as being on a board, but without the voting power.
Stay “operationally disconnected.” Offer advice with phrases like, “If I were in this situation…" Founders will make mistakes — let them. The key is to help them learn from those mistakes without stepping in too much. As an advisor, your main job is to provide input and ask good questions, which can expose areas that the founder can focus on developing. Be socratic but also supportive.
“It’s important to let go of your ego when becoming an advisor — empathy and experience result in the best wisdom,” Alkove says. “In the end, it can be a voyage of personal discovery and growth.”
Your pitch as an advisor should be about the full spectrum of value you provide, not just access.
Pitman brings lessons from extreme sports to advising. He knows the importance of realistic advice. The goal is to help founders push beyond their comfort zones.
“You want them to get to the next stage, so offer your expertise to help them achieve that,” Pitman says. “Talent only takes them so far.”
Nate Bek is an associate at Ascend, where he screens new deal opportunities, conducts due diligence, and publishes research. Prior to that he was a startups and venture capital reporter at GeekWire.
Disclaimer: The information provided here is for educational and informational purposes only. It does not constitute financial advice, and you should always consult with a qualified financial professional before making any investment decisions. Past performance is not indicative of future results.