Craig Vodnik, founder of cleverbridge, continues to support young entrepreneurs by answering iVenture’s questions about mentoring.

Hi Craig,

As you already know, the iVenture Accelerator works hard to match its resident and alumni teams with mentors. The Accelerator plans multiple mentor mixers and designs numerous ways for professionals to engage with the program either by advising, holding office hours, leading a workshop, etc.

You’ve offered incredible guidance to many of our teams—we know you’re passionate about mentorship, but we want to know more…

iVenture: What advice would you give young professionals looking for their first mentors?

Craig: I think there are three key things: 1) look for people who know your subject matter, 2) look for people who’ve been in your shoes and 3) find people who complement your weaknesses. If you aren’t good at raising funds, find a mentor that has that strength. If you are bootstrapping your startup, find someone that has done that before.

iVenture: What advice would you give potential mentors looking for their first mentees?

Craig: The best mentees are the ones that listen well and can understand how to take your experiences yet apply them to their specific situation. The advice given rarely can be applied one-to-one.

iVenture: At what stage in a career should an entrepreneur seek mentoring? Is there an ideal stage?

Craig: I believe that the ideal stage is as early as possible because not every mentor is the right one for every entrepreneur. This is a long-term relationship and you should talk to enough mentors to find the ones with whom you have a good rapport. If you wait until your business is scaling, you won’t have time and will almost have to “accept” the first people that you meet.

iVenture: Do/did you have mentors that significantly influence(d) your professional development?

Craig: I had a former roommate who started a business 10 years before I did so I talked with him frequently in the early days. He could relate to the decision-making situations that I had to go through.

iVenture: Describe your personal style as a mentor in one word:

Craig: Listener. I like to listen to the entrepreneur and not give any advice or ask questions until I hear the things that are on the entrepreneur’s mind.

iVenture: With which types of teams/people do you usually have successful mentor-mentee relationships?

Craig: Typically, where there’s a mutual interest in the topic and where the mentee is not afraid to share the good with the bad. Only with enough information can I be useful.

iVenture: How long do you expect to mentor a team/person once you start?

Craig: Because my specialty (and where I can add value) is in the startup and growth phase of a new business, I expect that the mentor relationship will usually last 3 to 5 years.

iVenture: What kind of situations or conflicts have damaged or broken your mentor-mentee relationships?

Craig: The two mains situations that resulted in damaged relationships are lack of follow-through on doing what was committed to and not remaining in regular enough contact. At minimum, do what you said that you are going to do and don’t be afraid to reach out and “bother” me. Persistence is a key sign of a great entrepreneur.

iVenture: In what ways does mentoring effect your own personal and professional definition of success? In other words, describe the sense of achievement (personal or professional) you receive through mentoring.

Craig: It might not be obvious, but I don’t think that I was mature enough to accept mentoring when starting my business. I’m impressed by young entrepreneurs who are mature enough to accept mentoring and I enjoy helping them if they are open to it. It’s the least that I can offer to the community to help the next generation.

Craig Vodnik is a co-founder of cleverbridge, the market leading full-service e-commerce platform for software and subscription model businesses. He is passionate about mentoring the next generation of entrepreneurs, spending his time at Catapult Chicago, with the Junto Institute or in conjunction with Techstars Chicago. Craig is also co-chair of the Digital Media & Technology subgroup at Hyde Park Angels.  He works with associates to source, evaluate and recommend companies for presenting to the broader membership of Hyde Park Angels.  His interests lie in e-commerce, software, Software-as-a-Service and marketplaces.