Key Questions
- Is there a difference between advisors and mentors?
- What are the pros and cons of working with advisors?
- When should I start working with an advisor?
- How many advisors should I have?
- Where do I find potential advisors?
- How can I determine if a potential advisor is a good fit?
- How can I get the most value from my advisors?
- How should I compensate my advisors?
- What are common mistakes when working with an advisor?
Start Here
Michael Skok – Want the Best Mentor? One Thing to Know…
(4 min read.) Skok emphasizes that the best mentors do not provide direct answers but instead ask probing questions, offer frameworks, and present multiple open choices. He highlights the importance of mentors being good listeners who encourage mentees to develop their own reasoning and logic. Skok advocates for the use of frameworks to track progress and the significance of open-mindedness for fostering innovation.
Suhail Doshi – How to Approach Someone to Be Your Mentor
(2 min read.) Instead of directly asking someone to be your mentor, which can feel awkward, start by seeking small pieces of advice and gradually build the relationship. Suhail suggests that if the person enjoys interacting with you, the relationship may naturally progress to mentorship or advisory roles. Doshi advises reaching out via email, Facebook Messenger, or LinkedIn, proposing a short 30-minute meeting and providing questions in advance. Initial meetings can be over the phone to save time. According to Doshi, the key is to approach people without overthinking, see if there’s a good fit, and enjoy the process.
Sophia Amoruso: How to Get the Most Out of a Mentor
(2 min read.) Sophia suggests being well-prepared by having clear questions and goals. She emphasizes the importance of providing detailed context about your current situation and goals to your mentor. Asking specific questions leads to actionable advice, and seeking introductions to the mentor’s network can be invaluable. Following up with a concise email of gratitude and action points is crucial to maintain the relationship.
Learn More
Jason Lemkin: Advice for Finding a Mentor (part of an AMA)
(4 min section of longer video.) Jason’s key advice includes avoiding mediocre mentors and opting for those who have proven success in their fields. He suggests having two types of mentors: one about 18 months ahead in experience for relatable and immediate advice, and another who is significantly further along, four to five years ahead, for broader strategic guidance. This structure provides a balanced perspective that can help navigate both current challenges and long-term planning.
Sophia Amoruso: 3 Tips for Working With a Mentor
(2 min read.) Sophia shares three valuable tips for working with a mentor, inspired by insights from ClassPass founder Payal Kadakia Pujji. First, she suggests finding a mentor through your network for a warm introduction rather than cold-calling, and be clear about your goals. Second, be honest with your mentor. Avoid posturing and be genuine to receive real feedback. Third, don’t fear your ideas being stolen; focus on swift execution.
Hiten Shah – You’re Mentoring the Wrong Way
(3 min read.) Hitan argues that most mentors fail by imposing their experiences on mentees instead of fostering individuality. He criticizes the approach of “telling” rather than “listening,” advocating for mentors to ask questions that help mentees think critically about their goals and weaknesses. Shah’s exceptional mentor listened deeply and acknowledged that success paths vary. Effective mentoring, Shah concludes, is about strengthening the mentee’s resilience and embracing individual paths to success.
Michael Seibel, Harj Taggar, Brad Flora: Top Ways Startups Waste Money
(4 min section of longer video.) In this video segment, Seibel discusses the pitfalls of spending money on advisors in startups. He notes that many founders feel pressured to give equity to respected individuals or those they have past relationships with, but such advisors rarely make a decisive impact on a company’s success. Instead, valuable advice often comes from investors or domain experts who offer their insights for free. He emphasizes that founders can often push back on equity demands, significantly reducing the percentage given away. According to Seibel, a useful strategy is to ask potential advisors to invest in the company, turning them into shareholders incentivized to offer genuine support.
Elad Gil – Bad Advice (from investors)
(3 min read.) Elad discusses how founders can receive well-intentioned but ultimately unhelpful advice from investors. Examples of poor advice include irrelevant partnership introductions, misguided product feedback, inappropriate venture capital intros, and ill-timed hiring suggestions.He advises founders to seek multiple opinions, question assumptions, and ensure that the context of their specific situation informs their decisions. The key is to balance listening to investors with the confidence to make independent decisions based on a deep understanding of their own business.
Jamie Miller – Find a Tough Mentor, You’ll Thank Them One Day
(3 min read.) Jamie talks about the need for a modern approach to mentorship, one that is direct and rooted in the daily grind rather than lofty, timeless wisdom. Miller advocates for mentors who provide honest, sometimes tough feedback, with a genuine interest in personal development. She highlights the importance of productive friction in teams and encourages building a diverse lineup of trusted advisors who challenge groupthink.
Jyoti Bansal – Can’t Find a Mentor? Try My ‘Rule of 10’ Instead
(6 min read.) Jyoti shares an innovative approach called the “Rule of 10” for those who struggle to find a mentor. Instead of relying on a single mentor, he suggests seeking advice from 10 intelligent individuals with diverse perspectives. This method helped him build successful companies like AppDynamics by providing a comprehensive view on issues such as pricing strategies. Bansal emphasizes the importance of selecting a broad range of advisors, respecting their time, and iterating through the gathered insights until a clear understanding emerges.
Eric Migicovsky: Startup Advisor Equity
(4 min video.) Eric discusses how he found his own advisors, the importance of having a broad set of advisors and how to compensate advisors with equity grants.