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Last month, I committed to interviewing 100 entrepreneurs during 2019. I hit the ground running with my self-assignment, and have already held four online group interview sessions via , and interviewed 12 entrepreneurs. In the short amount of time since starting this mission, I’ve already picked up some tips, tricks, and lessons. The following six lessons are already helping me reach my goal more quickly and giving me more time to connect with entrepreneurs.
Lesson 1: Engage With Audiences Early
The first thing I learned is to take my own advice. I’m always telling entrepreneurs to get out there and engage with their audiences, customers, or investors before their products are fully baked. So, I did that. I decided to commit two hours per week to interviewing entrepreneurs, and I do so using the relatively new platform, . Blab is a live web show platform that allows users — including myself — to interview up to three people at once. After signing up, I sent an email blast to a small subset of my network of entrepreneurs to request the first round of interviews. The response was overwhelming, and I am booked more than a month in advance.
Lesson 2: Don’t Overthink
I didn’t overthink who to match up in group interviews; I didn’t spend time clustering certain startups together by industry or geography, for example. Instead, I let serendipity take over. In my first Blab, I included a company that makes organic skin care products, a digital health eMarketplace, and a B2B that connects vendors and suppliers of natural products. My second Blab included two seasoned entrepreneurs with educational technology (ed-tech) and marketing backgrounds, along with a young entrepreneur in financial technology (fintech). The variety of participants in each group interview made the connections and conversations wide-ranging and topical.
Lesson 3: Be Flexible
When scheduling interviews, I didn’t dictate a specific time because I wanted to see what worked for the participants. Thanks to the beauty of this online platform, these interviews can take place morning, noon, and night! At the moment, I’ve limited my interviews to only Tuesdays and Thursdays, but even that can change.
Lesson 4: Automate for Efficiency
Although my aim is to make individual connections with each person I interview, automating some tasks has made the process more efficient. For example, I automated the routine tasks like the email blast and follow-up emails. The sign-up process is also automated; the participants use my scheduler. Whoever signs up first picks the time for that day, then others log on and sign up for another open slot. By using this process, the available spots filled up more than a month in advance after just a few days.
Lesson 5: Amplify
I always advise startups not to sit on their ideas, so I didn’t either. Instead, I told my broader network about my 100-interview goal immediately. I asked for questions that I could use as a foundation for the interviews. Again, I didn’t overthink this and use the same questions every session; rather, I tailored the questions to the entrepreneurs in attendance. Doing so makes the dialog more lively.
Lesson 6: Expand on Good Ideas
Like a good startup, I am iterating on the idea of interviewing entrepreneurs. I next opened up the Blab to a small group of investors and startup advisors, and received an overwhelming amount of support and interest from this group as well. Of course, I also got the most questions and requests for more structure, which made me chuckle.
I look forward to the year ahead, when I will not only connect with more exciting entrepreneurs, investors, and advisors, but also continue to learn from the process. If you are interested in checking out these interviews, please join me on for the next great discussion or to watch a replay.
This article is not investment advice, nor is it a solicitation to buy or sell any shares. Read more about Clarke’s angel investments, including DailyWorth, .
Barbara Clarke is a member of the DailyWorth Connect Program.
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