November 24, 2020

How to play an active role in the success of your founders beyond the cap table.


Sham Sandhu, a leadership consultant and venture investor has worked with Kauffman Fellows for over five years, helping accelerate the success of Fellows through formal and informal mentorship. We connected with Sham to discuss the profoundly relevant subject matter of mentoring, particularly from the point of view of investors seeking to make a greater impact on their portfolio companies.

By working together directly with founders, on a level playing field as equals, Sham’s mentoring philosophy aims to empower investors and founders to grow relationships far more valuable than the cap table.

Although likely exceptional candidates for the task, many investors haven’t necessarily actively pursued mentoring their founders, for a variety of mostly psychological reasons.

For example, one might be inclined to view mentorship as an evolution of an apprenticeship or an internship. As such, there’s a transference of a power dynamic rooted in a formal power structure that acts as a counterweight to the soaring aspirations of successful mentorship.

In the following interview, we will:


What are the most common misconceptions about mentorship?

The most significant issue with mentoring is the terminology. I haven’t yet thought of a better term, but the terms “mentor” and “mentee” assume a power dynamic and imbalance, which is contrary to the ultimate goal of successful mentorship.

Simon Sinek, a hero of mine, notes that we shouldn’t call it mentor-mentee, we should call it mentor-mentor, which is closer to the general idea. My personal definition of mentorship borrows heavily from Gary Zukav: mentorship is two human beings coming together as equals for the purpose of mutual growth and learning.

A proper mentor-mentee relationship puts common growth first: it advances the personal development of both parties. Putting mutual learning at the forefront of the relationship eases the pressures of an otherwise asymmetrical power dynamic.

While a formal mentor-mentee framework may seem rigid and intimidating, it doesn’t have to be. To better explore this, it’s worth reverse-engineering how human beings form relationships with one another–we call them friendships. The friendships in your life have blossomed organically in due time, and there may have been a great transference of ideas, experience, or characteristics in the course of this relationship.

A friendship isn’t built on a transactional tit-for-tat, you give me this and I’ll give you that. We naturally share our values and experiences because we want to and feel invested in the success of the other individual.

The serendipitous elements of a friendship are overshadowed by the structures imposed by formal relationships, such as that of investor and portfolio company. A core element of my practice, which I call the Art and Science of Connection, is exploring how to remove the walls that allow human beings to connect and facilitate the flow of information and experience.

Most people jump into the assumption that mentorship is a one-way street, which puts antagonizing pressure on the relationship. Mentorship is an exploration of mutual growth and learning for both parties. Personally, I’ve gained so much more from being a mentor than when I’ve been a mentee. Everyone reading this is capable of forming relationships like this already within their own network, but few venture out to do so.


How to overcome the most significant obstacles to a successful mentoring relationship?

If I could have one conversation to clear this up, it would be around creating a level playing field– building a relationship of equals rather than that of superiors and subordinates.

If you don’t feel like an equal, either as an investor or founder, this insecurity may make you feel compelled to give the other party something. If the relationship is framed as a continuous reciprocal act of giving, it becomes less about personal growth and learning.

Mentoring isn’t a noun– it’s a verb. It’s not something that is done to you, it’s something that you do, with the help of another.

Another obstacle to great mentorship is the Imposter Syndrome or feelings of personal inadequacy or deficiency. This prevents a great number of potentially great mentors from taking on the mentor mantle. They may feel like they have nothing to offer or they don’t have the time to make a substantial difference, which is far from reality.

This obstacle can be overcome by clarifying and articulating the expectations of the relationship and what each party can contribute based on their experience.

Outline what your mentor relationship is, what it isn’t, what it can be, what it can never be, your role and responsibility that will make it successful.

Your relationship should encourage vulnerability, so it helps to negotiate clear ground rules around confidentiality.

As a mentor, you don’t have to have all the answers, but someone in your network might be able to help. You can also create experiences to help the person on the other side of the table to learn by doing. Focus less on what experiences you have, but more so on what you and your mentee want to learn, and how you can do it together.


What role should investors play as mentors?

The job of the investor is to be in the top three phone calls of the best founders.  

A relationship between investors and founders can far exceed the association of the company and the venture capital firm. Your goal should be to be one of the first three people founders call when they’re going to start a company, when they’re going to raise money, and when they have a problem.

To become this figure, you must actively work on the relationship over and above the founder’s role in your portfolio.

The first step is to make founders feel seen, heard, and understood as a human being. They don’t want to feel like a line in the spreadsheet or a multiplier in your quarterly report. Founders want to understand that you, as an investor and fellow human being, care about them and that this care goes beyond the company’s growth.

If every interaction is a direct attempt to only make a positive impact on the company, you’re in a transactional relationship. This may work well within the confines of your professional relationship as investor and founder, but it’s not likely to establish a continuity of goodwill that places you at the forefront of their council of advisors. You can’t build a truly meaningful relationship on transactional conversations.

Founders and investors must go beyond a series of transactional engagements in order to come together as equals for the purpose of mutual growth and learning. The relationship needs to be transformative; it has to be about mutual growth.  Being in the top three phone calls of the best entrepreneurs and founders isn’t about one single transaction, it comes down to nurturing the relationship like an organism over an extended period of time.

Investor-mentors must be very intentional in making founders feel like equals, and this requires a strategic dismantlement of a default power dynamic. Make it clear that this relationship exists beyond the cap table, and that you’re both on a mission for personal learning and understanding.

Pick a real-world problem that aligns both parties, and use the challenge ahead as a platform for the transfer of information and experiences. In the investor-founder relationship, this mission is fairly visible: the success for the company, and as such, the success of the founder. How can we construct a mentoring relationship to achieve the end goal?

Going from a place where you feel something is expected of you, into joining forces to find creative solutions, helps alleviate whatever psychological concerns you may have.

How can you both build a relationship in which you look forward to meeting together? Viewing each other through the lens of being humans solving a problem as opposed to your professional roles might help facilitate a more effortless exchange of ideas.


What role should founders play as mentees?

Building a foundation on clear parameters and objectives is the best way to overcome the psychological barriers for both mentors and mentees. Both parties have this responsibility, but maybe more so the mentee.

When the ask is being made–will you be my mentor– the first question is why. As a mentee making the ask, you must go in hugely prepared with examples of what you seek to gain from mentorship. Clarity and simplicity can untangle some of the ambiguities that come with the concept of mentorship.

Enter the conversation with the top three things you’ve researched about the mentor that genuinely inspire you and urge you to learn more, become a better entrepreneur, or whatever your ultimate goal is.  

As a mentee, you should be aware that your ask may trigger some inklings of imposter-syndrome thought patterns. Be prepared to communicate why your potential mentor can make an enormous difference in your life, how they may be able to do so, and how this relationship will be dedicated to mutual growth.

Help the mentor visualize a relationship where they aren’t a kind of queen on the throne, but have something to personally gain as well.

It’s less “these are the reasons I want you to be my mentor.” It’s more like, “these are the questions I have for you, and these are the things I’m curious about.”

There has to be a common ground of interests, be they personal or professional. On some level, you’re both trying to answer the same question, but from different angles. Mentees can bring fresh ideas and new perspectives, whereas mentors can offer more structured guidance.

A common frustration founders feel is that they’re pouring all of their expectations into one person and one relationship. The mentor-mentee relationship takes on do-or-die undertones.

You’d never want a company with a board of one person, so why should your mentor-mentee relationships only have one person in that room?

I’d invite you to think about their mentoring relationships as a suite or a board, in the same way you’d run a company, or how you’d run your life. We all have advisors in our lives– we call them friends. Hopefully, we don’t just have one friend that we go to and ask for advice.

Different people bring different things. For our personal advisory board, we’re looking for range and perspective.

By distilling an awareness of the type of help or guidance you need, and through an articulation of that need, you can better understand the type of people you need in your life to fulfill your needs.

“This is what I need from you, and this is the sort of role I’d like you to play”

By having multiple mentors, you also ease the pressure of expectations on every individual one. It doesn’t seem that you’re looking at your single mentor to answer every problem you have– you’re coming to them for one thing, which makes things drastically more simple.


How much time should be allocated for a meaningful relationship?

To better answer the time allocation question, it’s better to work back from what you need or expect from this relationship, and then reverse-engineer the time necessary to get there.

Some relationships are more high-touch, others are less. Some duos meet once a quarter, others meet once a week. Remember, if you’re looking at your mentoring (or mentee) relationships as a panel of multiple individuals, you don’t need a high-velocity of touchpoints with each individual.

However, you must be very clear about what you need and what role you need the mentor to play. This role may change within the relationship, and articulating your needs will help you both make the absolute best use of your time.

For example, in the beginning, you may need them to be a mirror, but later on, you may need them to be a companion.

There is no prescription for time: your first job is to make each other feel seen, heard, and understood. You should both be able to leave with a firm affirmative answer to whether or not your time together was well spent.  

Once you’ve established a level playing field and trust, you can have an honest conversation: how much time do we really need to spend together? 

Think about your friendships in life and within the industry– are those built on prescriptions? You don’t say, “oh I need to speak to my best friend, I’m going to need 3 hours per week until Q4 2024.” Each relationship can be nurtured with a different amount of time, and this can change throughout the course of the relationship.


What happens when you’re at the peak? Who do the industry’s most accomplished seek out?

You’d think that accomplished individuals, the Mary Meekers and Marc Andreessens of the world might somehow be complacent and have nothing left in the tank, but it’s quite the contrary. These individuals tend to be incredibly curious and hungry in their passion areas of knowledge, and are masterful in their ability to seek out the individuals capable of accelerating their learning. 

The goddesses and the gods of the industry operating at an exceptional level all have a very powerful and active board of advisors– they may be called mentors or they may not.

I think if we feel like we have nothing left to learn and there’s no room for growth, we really need to ask ourselves some questions.

At those higher points of accomplishment, the appetite for information only tends to increase, and the mentor-mentee relationship should be viewed as a platform to accelerate your discoveries.


Final Thoughts

Investors have much more to gain from mentorship than they have initially considered.

Whether you’re a VC, family office, or foundation, your organization is charged with an individual purpose. Your organization faces many of the same challenges founders do. You’re also a fundraiser– you need LPs, you have stakeholders to consider. As such, it’s not uncommon for founders, as mentees, to transfer critical lessons that apply to successfully building a team and navigating obstacles in your own firm.

To drive a successful mentoring relationship with your founders, begin by doing two things:

  1. Level the playing field. Distill the relationship to two human beings coming together as equals for the purpose of mutual growth and learning.
  2. Make the other party feel seen, heard, and understood. It’s always deeper than investment credentials, title, startup, or role.

Keep yourself and your mentee accountable to a relationship designed for mutual exploration.


Meet Sham Sandhu: Sham Sandhu is a leadership consultant and venture investor on a mission to help individuals and corporations to grow creatively, commercially, and strategically through authentic connection. Sham has worked with Kauffman Fellows for over five years, helping accelerate the success of Fellows through formal and informal mentorship.


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