What’s your calling?

Work session with Amanda Montgomery, founder of Hummingbird Gardens

I originally wrote this post on a sleepless night in June 2016. It captures a lot of my daily work and why — even though it takes a lot of time and energy — I can’t give up this aspect of my work: Advising founders one-on-one. A couple of changes since the post initially went live: My mentees have changed, some dropped off, many new ones joined. More than ever, I think of myself as an advisor, not a mentor. Mentors are experienced entrepreneurs with years of entrepreneurial experience under their belt. That’s not me. I have never started my own company and while I have worked through many of the issues that first-time founders go through, I never experienced them first hand. Which is why I am so grateful for all the other mentors in our network who can lend that expertise. Despite some of these changes, the pure excitement and joy of working with mission-driven founders remains very much the same! Enjoy reading!


Tuesdays are my favorite days because Tuesdays are mentoring days. Given the number of hats I wear, every day of the week is dedicated to either building a community of sustainable businesses in Central Virginia, accelerating student founders at Virginia Commonwealth University or planning an Unreasonable Lab. And Tuesdays are the days on which I mentor mission-driven founders through the Chamber’s THRIVEprogram. If you ever need advice on how to start or grow your business and you are in the Richmond area, this is a great pool of incredibly smart and committed business mentors! And it’s free-of-charge. A quick round of applause to Greg Hofbauer and his team who created this fantastic program as a resource for our startup and small business community! End of sidetrack.

If you follow me on social media, Tuesdays have at least one message that sounds something like this: “I hope you all had a great Tuesday! I got to work on inclusive business, clean tech and a local agriculture! Richmond is a great place for startup founders and mentoring opportunities!” (5/31) or “Tuesday is mentoring day! I talked travel services, sustainable consumption, mental health and equal opportunities for job seekers with special needs. Now I’m off to William & Mary to talk about B Corps with Ross Decker! Stay productive!” (June 7). They are not always my most eloquent posts; I often hastily type them on my way to my next meeting or in the coffee line with my next mentee already waiting.

I was zapping all over Richmond/Ashland yesterday for meetings and had some time in the car to reflect on why I am so fired up on Tuesdays. The answer: Mentoring. I get really excited about mentoring. Here are a few of the reasons why:

For one, I love working with entrepreneurs on a one-on-one basis. While a lot of my efforts focus on community building, having the chance to spend an hour with founders talking about their day-to-day realities brings me back to what I feel is my calling: empowering entrepreneurs to build successful, mission-driven companies. It gives me the sense of being connected with what’s happening on the ground. In a larger effort of growing the most founder-friendly startup ecosystem on the East Coast, understanding the woes and daily grind of entrepreneurs gives us a lot of direction as to where to focus our efforts. Mentoring allows me touch base on a regular basis and stay connected to these pioneers in the field.

Secondly, to me, the beauty of sitting down with them every two to four weeks is a fresh perspective on the bigger picture of their efforts. It is incredible to see the progress some of my mentees make over the course of two weeks. Of course, everybody is different. With some mentees change can feel incremental at times; there are weeks where they don’t move ahead. But then there are the full-timers and some outstanding part-timers who will knock items off their Basecamp to-do list a week in advance. At each meeting they come around with some unforeseen development or opportunity. They hustle. All. The. Time.

It is these committed founders that fuel me with adrenaline and excitement about the work I do. It costs them sleep the way it does me right now (it’s 3 a.m.); they work long hours and weekends; they forego their social life. Yesterday, I met with a founder who is working to set up a sustainable fashion brand while creating economic opportunities for women in disadvantaged communities. She is aligning her independent study and Capstone project (both requirements for her masters) to serve as market research for her venture. Even though she can’t work on her venture full-time at this point (full-time job and graduate student) she is doing everything she can to set herself up for success and do her homework before launching. Another mentee comes up with great instagram campaigns and product ideas because she cares so deeply about what she does that she constantly thinks about how to share that passion with others. A team of two founders I work with spent the last six weeks running their program from 7 a.m. to 2.30 p.m., followed by several hours of part-time work only to go home and whip up event concepts, sponsoring strategies and partnership proposals until the next morning. This level of genuine dedication is incredibly energizing, and makes it so much fun to work with them! I look forward to these meetings because I know they are going to surprise me.

And after all, it is easy to get excited about working with these guys; many of them are driven by their desire to create lasting change for the disadvantaged. To some, it is their venture’s core mission, for others it is a give-back-to-the-community program. Either way, I get very invested because none of them are motivated by becoming rich (If you want to become rich, don’t launch a startup!); more so they are driven by a genuine passion for whatever it is they do, by a motivation to contribute to society in a meaningful, responsible way. And that’s where we click. In some meetings I can’t keep up with my own thoughts, I end up manically hammering on my keypad to make sure I capture ideas, thoughts and questions before the next one flashes up, my forehead in deep creases to hold it all in. I get excited to the point that I wish I was running their ventures with them. Then I remember that being an entrepreneur is not my calling. And my forehead relaxes. Helping people start and grow mission-driven businesses, and creating a supportive ecosystem around them — that’s what I’m here to do.

By the time Tuesday night comes around, I am nothing short of exhausted and drained. My forehead gained a few more wrinkles and I have several hours of follow-up ahead of me: making introductions and recommendations, sharing reading materials, updating to-do lists and coordinating calendars, providing additional feedback. And even though it often takes me a few days to get up-to-speed, I can’t wait for the next Tuesday to do it all over again.

What’s your calling?