Lessons Learned: Mentoring with TechStars and First Round Capital

Insights I’ve gleaned while supporting entrepreneurs and marketing leaders with TechStars and First Round Capital

Whether it’s mentoring a market leader to help them unlock the potential of them and their team, or learning about how you can strengthen your Go To Market strategy or approach to diversity, there’s an art and humility to sharing your experience.

At 5&Vine, mentorship is a vital part of our service offering. It’s a way for us to share knowledge we’ve acquired in our extensive work with Challenger Brands in the hopes of shaping businesses that better the world and positively influence culture.

Over the years, I’ve engaged in a number of mentorship initiatives, including being on the Design Team of the Aspen First Movers fellowship, the University of Toronto’s Venture Mentoring Service, Mentor in Residence at the Presidio Graduate School, as well as TechStars and First Round Capital. The commonality across each of these programs is their belief that mentorship is about tapping into the generosity of the community and creating lasting, deep connections with others.

As the first tips of TechStars’s Mentor Manifesto read:

  • Be socratic.

  • Expect nothing in return (you’ll be delighted with what you do get back).

  • Be authentic / practice what you preach.

  • Be direct. Tell the truth, however hard.

  • Listen too.

  • The best mentor relationships eventually become two-way.

So, in the spirit of sharing knowledge, I wanted to highlight some of the tips and insights I’ve gleaned while supporting entrepreneurs and marketing leaders.

1. Be both the student and the teacher. 

Seek first to understand before being understood. Approach mentorship eager to learn about your mentee, their context, their aspirations and challenges and, when asked, share your successes, failures and hard-fought lessons.

Typically, the individuals I’m mentoring already have the answers they’re looking for but they may be lacking the conviction to believe it is the right path forward.

2. Acknowledge your privilege.

I’ve gained a deeper appreciation for the role my privilege plays in my success, and the ways in which my identity both aid and hinder me. I’ve realized the strategies I’ve employed to succeed are not always universally applicable to others.

In mentoring BIPOC entrepreneurs, I’ve learned about the daily biases they face and the funding and talent networks they’re excluded from, which has required a different approach to winning. There are different conversations you can open up about when the person mentoring looks like you, and it’s been helpful and cathartic to share lessons and strategies about deftly navigating politics and discrimination.

3. Embrace empathy.

Despite pregnancy being an integral part of life, there still remains huge anxiety for women sharing that news with their employer. Throughout my time mentoring, I’ve supported a number of women developing their strategy, worried about how their pregnancy might impact their job and employment.

Even when taking paternity leave, where I was explicitly told this would be a career limiting move and advised not to by a firm’s top leadership. These are experiences that need to change but also reinforce the importance of empathy in mentoring.

4. The network effect. 

Mentoring is more than just listening, empathizing and sharing content. It’s about determining how you can best support your mentee with the network you’ve established.

Consider amplifying their calls for support or successes, connecting them with prospective new hires or angel investors, manufacturing or service partners. Don’t be afraid to leverage your network to support them in their journey.

5. Acknowledge, affirm and celebrate success. 

Entrepreneurship is a lonely journey. Often the pain of failure seems to endure while the wins feel fleeting.

Not only that, but leadership can often result in a small circle of people you can authentically share your struggles with. As you listen and support your mentee with their challenges, remember to build them up and celebrate their successes. Remind them they are on the right path, considering the right questions and have great intuition.

6. Ask the tough questions and hold them accountable. 

Differentiate between platitudes and earnest intent. Help your mentee grow and stay true to their goals.

If that means you have to call them out or hold them accountable, do it. Don’t shy away from some tough love.

No matter your sector or specialism, mentorship matters. As a symbiotic relationship that works both ways, good mentorship has the potential to empower people at every stage of a business.

To learn more about 5&Vine’s mentorship services and speaking opportunities, meet our founder and CMO Rahul Raj.


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👋 I'm Rahul, founder and CMO at 5&Vine. Reach out to schedule an intro call about your marketing challenges and let's assess how 5&Vine can help your brand win.

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