A VC explains how mentoring helps early stage startup founders succeed

- October 6, 2021 3 MIN READ
Photo: AdobeStock

Working for a venture capital firm, I’m lucky to meet and support hundreds of startups in our portfolio and beyond. Many of these startups are at the earliest stages – they might not have a product yet, or perhaps their startup is just an idea.

At Blackbird, our mission is to invest in wild hearts, with the wildest of ideas, right at the very beginning, so over the past year, I’ve been building our Giants community – a mentoring program to help founders at the beginning of their journey with advice and support from fellow founders, operators and investors.

We’ve now had more than 300 founders get mentoring through the program – here’s where I’ve seen mentoring can help early stage startups, and how founders can seek out meaningful mentors.

1. Help you define your ambition and how to get there

If you’re just starting out with an idea, mentoring might feel too formal or a step too far along to consider.

But mentoring doesn’t have to be an ongoing, formalised arrangement. It could be as simple as developing a list of relevant people you admire who have experience growing a startup from 0 to 1, and sharing your idea with them for feedback and insights. What common themes emerge, and what needs to be resolved for you to move forward on your ambition?

Advice for founders: One of the things I’ve seen work really well in Giants is idea stage founders using mentoring to get feedback on the size, scale and feasibility of their idea, or how to best validate the hypothesis they’ve come up with in response to a problem. This often leads to more user research, validating the solution in more depth, and ultimately creating a stronger product.

2. Challenge your assumptions 

The best mentors help founders realise something they already knew about themselves or their business through coaching. This could be through challenging their assumptions about their customer, getting them to step through the problem they are exploring in more detail, or asking the right questions to get a founder thinking about something in a new way.

While there’s no shortage of content out there to support your founder journey, having a direct conversation with someone who has been there before can have a much more powerful impact. It could be an investor reviewing your pitch deck, or a fellow founder sharing their own learnings from a similar time in their startup.

Melia Rayner

Melia Rayner from Blackbird Ventures

Advice for founders: While it feels nice to someone that affirms and agrees with your choices, it’s important for a mentor to help you get the best from yourself and challenge your thinking when needed. Look for people who are willing to be honest with you, and who don’t shy away from difficult conversations.

3. Identify opportunities and make connections

While you shouldn’t enter into a mentoring conversation purely to pump someone for their relationships, networks or status, you should have an idea of what opportunities this person represents – no doubt it’s why you’ve contacted them in the first place.

I’ve seen mentors go above and beyond for founders they’ve mentored, making connections, offering ongoing advice, even joining their startup as an ongoing advisor, senior hire or angel investor. Just remember, you need to earn the right for this person to go above and beyond for you – they’re not automatically going to open up their contacts or write an angel cheque, you need to demonstrate why you deserve the opportunity and give them the opportunity to become further involved, without being pushy.

Advice for founders: Have a clear idea of how your mentor can help you beyond the initial conversation, and make it as easy as possible for them to do so (if they’re up for it). For instance, if your mentor has great connections in startup investment, make sure you have a pitch deck ready, and an intro email they can use to connect you.

4. Build a relationship with someone you wouldn’t have felt comfortable approaching otherwise

Our Giants founders often tell me that they would have never felt comfortable reaching out to their mentor without the program, but with more social media platforms, virtual communities and industry groups than ever, there are many ways to approach someone you admire for a mentoring conversation. People are generally willing to help where they can, and are more likely to agree to a meeting to help you figure something specific out in your business than a general “introduction” coffee chat.

With that said, make it clear what’s in it for them, and make it easy for them to engage. Be straightforward about why you admire this person, what you’re asking for and the time commitment – I suggest 30 minutes as an initial chat. While it can be intimidating to cold-contact people you admire, you never know who will reply – they might become your biggest supporter.

Advice for founders: Don’t be afraid to reach out. The worst that can happen is that they don’t reply, or aren’t interested.

* If you’ve got a startup idea you’d like to get feedback on, or are in the early stages of building your company, join our Giants program to get free, fully-virtual 1:1 mentoring from the best people from companies like Brighte, CultureAmp, SafetyCulture, Atlassian, Dovetail, Baraja, Airbnb, and Stripe, plus VCs, angels, and impact investors.
Applications for the next cohort are open until 20 October at blackbird.vc/giants