Experienced Mentors Share Their Best Tips from the Trenches

JT Kreager and Aggie Haslup have served as mentors to multiple Rev1 portfolio companies. Each brings extensive experience and expertise as executives and startup investors, but perhaps their most important quality is that they are both excellent listeners. For this article, however, we asked them to talk.

MM: Advising and mentoring a startup is a commitment. Why did you decide to do it? 

JTK: A few reasons come to mind. The first is giving back and helping others. I’ve had the benefit of mentors along the way for more than 25 years, so I feel like it’s the right thing to do. Second, I’m a venture partner at NCT Ventures; we work with Rev1 as part of the whole VC community, which is becoming more vibrant here, so I want to reach out and broaden my horizons in the startup community with more networking. Finally, I love learning. In sharing my experience and knowledge, I learn from other people and other perspectives. Mentoring keeps me sharpening my own saw.

MM: Aggie, after a career as an executive in both startups and billion-dollar software companies, and traveling domestically and internationally 75 percent of the time, why have you switched gears?

AH: I was born and educated in Ohio. We raised our four children here. I had wonderful mentors throughout my career. From a personal perspective, the most rewarding aspect of my experience in high-tech was building talented teams, helping people along their career paths, and developing leaders. After the last company I was working for was acquired, I decided to take a step back. Now I do a mix of business strategy, marketing consulting, executive coaching, and angel investing.

When I thought about how to give back to the community in return for what I have received, I thought about volunteering for Habitat for Humanity or in a food pantry. Then I thought about how people have used my skill set over the decades as a good listener, coach, and mentor, and I realized I wanted to help entrepreneurs create jobs. This isn’t the way I thought I would be defining my volunteer experience, but that’s the way it has evolved. I am mentoring startups to contribute to the community and to foster job growth in this state. My goal is to make entrepreneurs successful.

MM: In mentoring, it’s important to set the right expectations between entrepreneur and mentor. How do you establish that?

AH: I connected with Rev1 through X Squared Angels, where I had been leading due diligence for the group for the last couple of years. I was very upfront about the type of advising I could do. If it was legal expertise or in the retail space, that wasn’t me. I’m a software and high-tech executive who can advise on strategy, messaging, talent acquisition, and business development. If my entrepreneur needs more help in other areas, I can go back to Rev1. There are resources there for me and my entrepreneur; they will help us find the expertise we need.

MM: How do you suggest that a mentor gets started with a company?

 JTK: Go slow. Make sure there is chemistry. It’s about being a team, that you fit, and feel good about working with each other. Let the relationship take its course. One hour a week can easily become an hour a day. Some mentors and advisors even join the company full time.

I tend to look at the business from a holistic perspective; I tend to come in as more than a product guy or as a finance guy. It depends on the mentor, their background, and what their view and value add might be. For me, that’s focusing broadly on strategy and business development, looking at the whole company for how we might grow.

AG: Be realistic. Do you have the time to provide continuity of care, to borrow a term from the healthcare industry? An effective mentor will know the business, the strategy, the business partners, the CTO, and even the entrepreneur’s family. You have to respect the entrepreneur’s time and be available in a reasonable time frame when they call. Do you believe in the mission of the company, that there is a market opportunity for the product and a buyer with a budget? You have to believe in the company, and you have to believe there is a buyer who will pay.

MM: What do you look for in an entrepreneur?

JTK: I look at how competitive the entrepreneur is. They need to be very passionate about their business. I look for their grit, and if they are willing to listen or not—to their advisors and most importantly to their customers. Are they able to make constant adaptations? Entrepreneurs who think they know it all and can’t change the business around the market or customers usually spells trouble.

AH: Coachability. Some entrepreneurs are more coachable than others. There has to be trust on both sides, and that requires some time.  I want to work with entrepreneurs who ‘know what they don’t know’ and are willing to surround themselves with people who have experience and expertise in areas they do not.

MM: You mentioned that learning is one of your goals for mentoring. Is there something that you have learned that has surprised you?

AH: Over the years of coaching entrepreneurs, I’ve found the difficulty that they have in giving up equity or a piece of their company either to attract talent or to secure investment capital quite surprising. I can understand it—they built the company and didn’t want to give up part of it to someone else—but to grow, especially to capture a startup’s window of opportunity, an entrepreneur has to give up some equity. Bootstrap funding is typically not the way a startup breaks through barriers.

 JTK: I’ve had situations where founders or managers who were very high up left the companies that they were heavily vested in and just walked away. I’ve seen it at the CEO level without even a two-week notice. You can’t hide from the stress of a startup. It’s there. Whether it is a mentor or an advisory board, every entrepreneur needs to be able to have conversations that you can’t have with anyone else.

MM: There are many ways mentors make a difference. What approach do you use that you’ve found to be powerful?

AH: I try to help the entrepreneur by saying, if I’ve heard you right, these are your priorities and focus for the next month and next quarter. Let’s write those down. Then the next time we meet, I hold them accountable. Some people aren’t used to that. Or life gets in the way, but if you are trying to grow your business and have decided that these priorities are where your focus should be, you have to keep on them. No matter what.

Accountability is so key, and there are so many opportunities for entrepreneurs to drift away from what they are trying to do. I try to help the CEO put on blinders, within reason, and to think in a balanced fashion.

JTK: For mentors from large corporations or big regional companies, use your network and connection to bring business to the young companies that you mentor. Be proactive about getting the startup’s innovation into those big companies. Large companies may be leery of working with a small business, so if there is a project where you see applicability, use your influence to get the startup an opportunity to run a small pilot, to make a good impression and to create a reference. To the extent that big corporations support the innovation that comes out of startups, the stronger our startup ecosystem will become.