When it comes to mentoring founders and investing in their businesses, we already know that diversity is the key to success. There’s no question that we need to listen to the voices and ideas of women and men and people of all races, ages, and walks of life.

Something to always keep in mind is checking in with your unconscious bias. Everyone has unconscious biases, but that does not make us bad people—we are just human. It’s crucial to constantly review our blind spots to acknowledge any biases that we have in order to make better decisions rather than simply choosing what’s familiar. The world of venture capital and business is historically comfortable with investing in white males.

In my recent blog post about what female founders look for when seeking out investors, I spoke with two founders that I have invested in, Katherine Regnier, founder of Coconut Software, and Alicia Soulier, founder of SalonScale. Considering what I’ve gathered from mentoring these women-led businesses, I’ve circled back with them to share lessons we’ve learned together and hear what they have to say about working with me. I’ve also had the opportunity to mentor Katrina German of EthicalDigital.ca and she’s shared some thoughts, as well.


The Personal Side of Mentoring

When it comes to mentoring men versus women, it’s not about being male or female. Every situation is different, and it should always be about the founder. It has nothing to do with whether they are a man or a woman, but rather, who they are as a person and how they are as a founder.

Before spending a cent, I always make a point of getting to know entrepreneurs personally: hearing about their family, how curious they are, what their opinions and values are, etc. You have to be on the same page with the person you’re talking to when mentoring or investing, and all of my investments are made based on some sort of personal contact that’s not necessarily business-related. I’ll set up a 4-hour interview that’s not an interview to go for a walk or grab a drink so we can loosen up, chat, and gain trust on both sides.

“Neal just listened and then gave me advice on how we could figure out a support system, and he understood the whole life experience. He was super empathetic.”
—Katherine Regnier

Yes—part of mentoring is guiding them through decisions for their business, but a lot of it comes down to leading with empathy and listening to what founders need. How can I support them and provide value?

“Neal has more of a coaching mentality than an investor mentality; he wants a relationship rather than focusing on the investment. He assesses how coachable you are, and he wants you to have a real relationship with him so that you can have real conversations.”
—Alicia Soulier

“It’s not all business with Neal. He likes to know more about you as a person and then he shares advice and guidance when it’s the right time. He often makes sure that I am not working too much and burning out.”
—Katrina German


The Business Side of Mentoring

Once mutual trust exists, then we can talk business. From here, I’ll have a better understanding of what I can do to help and what effective communication will look like between us. We can begin having those hard conversations, work on being honest and transparent, and I’ll get a gauge on when to push and how hard.

“He knows when to push and push hard, and he knows when he needs to be empathetic. His mastery is in understanding people. People, passion, performance, and perseverance, are all values we’ve built into our corporate culture—and a lot of that comes from Neal and his networks. Our culture was based on the backbone of his ideas around people.”
—Katherine Regnier

There will inevitably be endless questions and observations when building a new business, and I encourage entrepreneurs to ask all of them. A founder is with their company 24/7, compared to investors who are only there once or twice a week in the early stages. And since they know everything about their business, they can’t hide any problems when we work together. Every day is a new day, we can fail together, but we can’t make it personal.

“You are going into hard rooms. Neal will say, ‘I’ll speak up for you, but not for you; I’ll coach you, and then it’s yours.’”
—Alicia Soulier

And it’s true—as a mentor, my job is to guide you in the decision-making process but not call the shots.

“He asks the hard questions just to make sure you are thinking of all of the angles. It’s less about whether you are right or wrong, and more about are you thinking about all of the risks and opportunities.”
—Katrina German

Mentors should be keeping in mind that founders are replicating what investors have done with them, such as hiring and trusting a team. The team they hire may not be perfect, but who do they trust the most, and who will be there through it all? Trust sets the foundation for the business, and then you can talk about solutions if people need to be fired, where money should be spent, what to do if things are going bad, and how to make other tough calls.


The Importance of the Personal Side

Although we’re in the business of moving forward and getting things done, I firmly believe that it’s the people and personal side that matters and how we’ll be working together. I can’t stress empathy enough as a mentor since your behavior and how you treat people makes or breaks whether people want to work with you.

“I’ve never felt treated as a female, but always as an entrepreneur.”
—Katherine Regnier

Men or women, black or white, young or old—mentors need to be treating everyone differently since everyone has different motivations and goals. Knowing whether you need to be tough or be human will boil down to the relationship you’ve built with them and the understanding on both sides that tough decisions can’t be made personal.

“Neal has also aggressively made me focus on my family and mental health. He always asks about my family. He’s genuinely curious to make sure everything is okay.”
—Alicia Soulier

Treating each founder individually doesn’t mean focusing on one group or being any tougher on one versus the other, though. Who they are and their background should not be subject matter, but instead, all part of the experience of getting to know them and how to work with them successfully.


Because at the end of the day, we are just human. Mistakes will be made, but those are opportunities to learn together and build something big.

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