Startup founders have infamously unpredictable daily schedules as they work to establish and grow their businesses. What does such an entrepreneur’s weekly, daily, or even hourly routine look like when sometimes there aren’t enough hours in a day? In The Startup Diaries, founders walk us through a week in their lives and show what it really takes to get a fledgling business off the ground.
When Yemi Adewunmi co-founded Civic Eagle, a company that provides legislative tracking software for policy professionals, in 2015, it was conceived as a mobile app for citizens to gather information about their representatives and debate policy issues. But Adewunmi and her partner, Damola Ogundipe (he’s CEO and she’s the chief product officer), struggled; after more than a year on the market, and even with a presidential election looming, the app had only a few thousand downloads.
“We totally underestimated how hard it would be to create what was essentially a social network,” Adewunmi says. “It was hard to raise money and usership, and we were like, ‘Let’s go back to the drawing board.’”
They decided to repackage their idea as a business-to-business platform, serving companies and nonprofits that need to closely follow legislation. One customer is a Minnesota-based organization called Voices for Racial Justice, which uses the tool to track bills on criminal-justice reform. “We were like, ‘We should target people who are already invested in politics and are open to innovation,’” Adewumni, a WeWork Labs member at WeWork Navy Yard in Washington, D.C., says. “Failing is important. It allowed us to pivot in a better way.”
In fall 2017, they pitched the new version at “Google for Entrepreneurs Exchange: Black Founders,” a weeklong immersion program for African-American entrepreneurs. Arlan Hamilton of Backstage Capital signed on as their first investor, and shortly after, they were accepted into two accelerator programs. By January 2018, Adewumni says, the business had kicked off. “Now we’re much more settled—we have 12 clients and a couple more investors.”
Below, Adewunmi shares a diary of a recent workweek.
6:30 a.m. First alarm goes off.
8 a.m. Review my agenda for the day and make a list of my top tasks in my Productivity Planner. Check my dev team’s Airtable, which we use to manage product and engineering tasks, to see if any questions or updates await me. (Half my dev team is in Nigeria, so it’s already the afternoon for them.)
8:30-9:45 a.m. Walk to Orangetheory Fitness, about half a mile from my apartment. I’ve been a member for almost six months, and it’s been a game-changer for me. Working out has not only been great for my health, but it’s also helped me destress and build confidence. It’s become my favorite form of self-care as an entrepreneur.
10-11 a.m. Make breakfast, shower, and dress, and commute to WeWork.
11:30 a.m. Weekly stand-up meeting with the exec team. As cliché as it sounds, we don’t really have major disagreements. We understand that no one knows the right answer all the time, and all we can do is test and learn, test and learn.
12 p.m. End our meeting early because I have to watch a webinar about the Aspen Tech Policy Hub fellowship. I’m applying, and the deadline is this week.
1 p.m. Meet with my Techstars managing director. Techstars is like the Ivy League of accelerator programs—really hard to get into. WeWork had one of the managing directors do a coffee-table talk with us, and Damola and I applied for a cohort called Anywhere—it’s a virtual mentorship-driven program that helps set you up for success, whether it’s for fundraising or product development or user acquisition. We got into the three-month program, which started in February.
Today, Damola and I have a weekly one-on-one video call to discuss goal setting, OKRs (objectives and key results), and KPIs (key performance indicators) for the next three to six months.
2 p.m. Call with a Techstars mentor about content-marketing strategies. During the first few weeks of Techstars, our cohort (Civic Eagle and nine other startups) went through “Mentor Madness,” a series of roughly 60 20-minute meetings with experienced founders, VCs, and experts, over the course of eight days. My team scheduled followup meetings with these mentors throughout this week.
3 p.m. Take a break to meet with a fellow WeWork Labs member and jam/vent about what we’ve been working on and things that are top of mind for us. It can be hard to find people who can relate to the founder’s journey, so it’s important for me to carve out this time.
4 p.m. Finally able to start working on my tasks for the day: Write a spec for a new notifications feature; draft survey questions for an inbound-marketing push; and update the job description for an open engineering role.
6:30 p.m. Run a quick errand and head home.
7:30 p.m. Another video call with my business partner and a Techstar mentor.
8:45 p.m. Dinner.
10:30 p.m. Send emails, check Productivity Planner for tomorrow.
11 p.m. Bed.
7 a.m. Roll out of bed. I have the same routine every morning, and it’s been shaped over the past few years. As an entrepreneur, you get to make your own schedule—but to have a routine that you expect every day is really important.
8 a.m. Check my calendar, Productivity Planner, and dev-team task manager.
8:30-9:45 Work out at Orangetheory, return home, eat breakfast, and get showered and dressed.
11 a.m. Today I’m working from home. I kick the day off with a meeting with my business partner to discuss lead-gen strategy. One of our objectives is to increase our sales pipeline so we can increase our revenue.
12 p.m. Check and send emails.
2 p.m. Walk to a nearby coffee shop to catch up with a friend.
3 p.m. Back home. Have a good conversation with another founder in my Techstars cohort. I’m in a mode where I can’t quite focus on my main tasks for the day. Being a founder, you have to balance working and networking. You need to be responsive and help people when they need help (because when you need help, they can help you). But that means some days you’re not doing any head-down work.
5 p.m. Video call with my Techstars cohort and managing director.
6 p.m. Another mentor meeting.
7 p.m. Work on the Aspen Tech fellowship application.
10:30 p.m. Bed.
7 a.m. The usual morning routine.
12 p.m. Lunch with other WeWork Labs members.
1 p.m. Product strategy meeting with my CEO, CTO, and one of our full-time developers. This was a strategic deep-dive into our product/software goals and our engineering-team processes.
2:30 p.m. Techstars homework. Today I’m watching videos about customer research, discovery, and empathy interviews ahead of our group session on these subjects.
3 p.m. Session with my Techstars cohort.
4 p.m. Call with my business partner. We do a virtual whiteboarding exercise to come up with a game plan for generating new sales leads.
5:30 p.m. Fireside chat with Cal Newport, author of Digital Minimalism, hosted by WeWork.
8:30 p.m. Catch up with a friend over drinks.
10:30 p.m. Finish and submit the Aspen Tech fellowship application.
12 a.m. Bed.
7 a.m. Same morning routine, including a workout. Working from home today.
12 p.m. Call with our engineers.
1 p.m. Research lead-generation, draft email campaigns, and check in with my business partner.
3 p.m. Call with a marketing expert as part of Techstars.
3:30 p.m. Eat lunch while listening to the audiobook of Bad Blood by John Carreyrou. For a while, I was skeptical of Audible, but then I realized that it works for certain types of books. Bad Blood almost sounds like a podcast, a true-crime story. I don’t think I would have wanted to read pages and pages of medical and blood jargon.
4:30 p.m. Check email and do more work on lead-gen.
7 p.m. Draft a design for an email newsletter we’re going to start sending to customers.
8 p.m. Dinner, Hulu, light work.
10 p.m. Bed.
7 a.m. It’s Friday and I’m taking my time, listening to my morning news podcasts in bed. On Fridays, my favorite tech-policy podcast, “Pivot,” releases a new episode. I also listen to “The Vergecast,” a technews podcast.
9 a.m. Listen to one of my favorite pop-culture podcasts, “The Read,” while I continue designing the customer newsletter from last night.
10 a.m. Listen to Bad Blood while getting a pedicure.
12:30 p.m. Head home for my weekly Techstars all-hands meeting, which we use to probe each other’s businesses and offer support. Each team reviews the OKRs and KPIs they’ll be tracking for the upcoming week. It’s a great learning experience.
2 p.m. Work on designing a new landing page and the email newsletter.
5 p.m. My last mentor meeting of the week. Hurray!
7 p.m. Dinner, wine, and The Umbrella Academy on Netflix. I’ve had an unusual number of meetings this week, and it’s been challenging to keep up with all the useful information that I’m learning, but it’s incredibly rare to be able to have access to such a group of experienced professionals. I don’t take it for granted.
Photographs by Foster K. White