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.
Lisa Skeete Tatum spent a decade working as a venture capitalist when she decided she wanted to try something new. But what? “I didn’t know,” she says. “Everyone expected me to know, including myself, and it felt pretty awful.” The silver lining to her temporary aimlessness was that it gave her the idea for Landit, a career pathing platform that offers personalized brand development, coaching, and more to people who want to grow or redirect their career—but don’t know where to begin. “Pivots are hard,” Tatum says. “I thought, if it’s hard for me—and I had a whole bunch of people trying to support me—then it might seem insurmountable for others.”
Initially, Landit was marketed toward women, but since officially launching in 2017, it’s taken a more universal approach. “Now companies are using Landit to not only invest in their women but also in their people of color, millennials, you name it,” says Tatum, a member at WeWork 1460 Broadway in New York City. Although the platform touts a “one size fits one” model—meaning your experience on the platform will be tailored to your specific professional needs—it’s as much intended for corporate use as it is for individuals.
“Great companies will always attract great people,” Tatum says. “The issue is, What happens when they get there? Do they progress? Are they able to bring the full measure of themselves? Too often, the answer is no.” That’s in part because company resources typically go to folks already in the C-suite. “The investment happens at the top of the pyramid, but most of us don’t get there,” Tatum says. “Landit wants to take all those things that would typically be reserved for the top”—like brand development and coaching—“knit them together, and put them in the hands of anyone.”
Earlier this year, the company raised $13 million in a Series A funding round led by WeWork. “Raising money, period, is hard,” Tatum says. “We’re one of the few companies led by a woman of color to have raised [that much].” With that round closed, Tatum is focused on staffing up and growing her company’s clientele. (She declines to share numbers: “You’d have to come work for Landit!”) Below, she shares how a recent workweek unfolded for the mother of two.
4:53 a.m. Wake up before my 5 a.m. alarm. Take five minutes to mentally run through the day. Head downstairs to our workout room to meditate for 10 minutes. (I’m a work in progress!) Jump on the Peloton for a 30-minute ride. Feels like 90.
6 a.m. Run upstairs to quickly get dressed, then back downstairs to make breakfast for the boys (they’re 17 and 15). Write out goals for the day.
7 a.m. Catch up with the boys and sync with my husband over breakfast. My younger son plays me his latest piano piece, and my older son tells me about his research paper. Realize we are going to be late.
7:29 a.m. Rush everyone to the car to head to school.
8 a.m. Take New Jersey Transit to the office in New York. I always sit in the quiet car. Today I listen to CNN on Sirius with AirPods. Get off the train and get pastries for the team at Maison Kayser.
11 a.m.–1 p.m. All-hands team meeting.
1:30 p.m. Zoom call with a current customer about expanding their cohort. We’ll often start by targeting a particular group within the organization, then roll out from there.
2 p.m. Conference call with attorneys to review pending customer contract.
4 p.m. Conference call with strategic partner to review the terms of contract. We haven’t announced this partnership yet, so I can’t say much.
5 p.m. Sync with VP of engineering on product road map. You have to listen to your members, because they will tell you what’s working in your product and what’s not working.
6 p.m. Commute home.
7:30 p.m. Hubby picks up dim sum for dinner. Sit around the kitchen table with him and our boys. Lots of posturing about who’s the best ping-pong player.
9:30 p.m. Back on call with Landit team members to review upcoming customer launch and contract. I hate the term “work-life balance.” I practice hyper-prioritization. You have to think about what’s the most important and impactful thing that you can do, and then everything else lines up behind that. If there’s a task or goal you need to achieve, focus on that and then move to the next thing. Otherwise, it takes twice as long.
11:30 p.m. Drift off to sleep.
5 a.m. Wake up. Take five minutes to mentally run through the day. Not up for Peloton this morning, so I opt for the kindler, gentler elliptical.
6 a.m. It’s a game day for my older son, and my turn for team snacks, so I place an emergency order for grilled cheese, cookies, and water from Panera for rapid pickup. Prepare breakfast. Discuss evening logistics with the entire Tatum squad.
7:15 a.m. Everyone out the door.
8 a.m. Train to New York. Read the New York Times on my iPhone. Check email and play Wordscapes.
9:30 a.m.–12:30 p.m. One-on-one meetings with each team member.
12:30–1:30 p.m. “LST Focus Time.” This time is sacred to me. I use it to think—about priorities, strategies—or to read up on something relevant to the business.
1:30–2:30 p.m. Interview several job candidates. We just closed our Series A funding, and the money we raised is all about scaling. We have to hire an A+ team to help us change the world!
4–5 p.m. Watch son’s tennis match. Glad I commuted back in time to see him crush it.
6–7:30 p.m. Virtual launch event with Fortune 500 customer. We introduce Landit, explain the benefits, then they’re off to the races.
9:30 p.m. Family time. This is where I get my joy.
10–11 p.m. Finish up Landit items.
11 p.m. Plan for the following day. Bedtime.
5 a.m. Wake up. Take five minutes to mentally run through the day. I always take the first part of the morning to ground myself. I think a lot of people just get up and start moving, and they may not have a plan.
6:30 a.m. Leave for the office. Send “I love you and have a great day” text message to family group chat so they have a note from me first thing in the morning.
8–10 a.m. LST Focus Time.
11 a.m. Meeting with Landit coaches to share updates, insights, and priorities for next month.
1:30–2 p.m. Interview a job candidate. We’re looking for folks who are naturally curious. Grit is also super important. And we have zero tolerance for drama—I mean zero—so we’re looking for folks that value transparency, because that’s one of our core values.
2–3 p.m. Landit investor meeting.
3:30–4:30 p.m. Call with potential new customer. I land it!
9 p.m. Have my first dinner and the kids’ second dinner. Ice cream for my husband.
11 p.m. Bedtime. Lights all the way out.
5 a.m. Wake up. Take five minutes to mentally run through the day. Peloton! Get dressed.
8 a.m. Breakfast with the kids.
9 a.m. Brainstorm with board member about go-to-market strategy for a new vertical we’re launching. (No spoilers!) As an entrepreneur you have to take advantage of your resources, and we’re very fortunate that we have some amazing board members.
11:30 a.m.–12 p.m. Landit candidate interview. Last one of the week. Two are standing out for me at this point: One took the time to sign up for the product itself. When he came to the interview, he said, “This is what I love. This is why I fit. This is how I would like to contribute.” I was like, “Get that dude right now!” The other sent an email three hours after her interview that bullet-pointed what she heard, what she was excited about, and some ideas she had.
12:30–1:30 p.m. LST Focus Time!
2–3 p.m. Pipeline review with chief business development officer. The pipeline is so robust it’s a matter of who we should approach next.
3–4 p.m. Financial reviews with CFO/accountant.
6 p.m. Family dinner.
8–10 p.m. Back online with Landit.
10–11 p.m. Mini TV binge time. I’m a big foodie, so we watch a little bit of MasterChef.
11:30 p.m. Bedtime.
6 a.m. Sleep-in-late day! Take five minutes to mentally run through the day. It’s an elliptical morning. Get dressed. Reflect on the week and my accomplishments.
8 a.m. See the boys off to school.
9:30 a.m. Customer meeting at their office to discuss the next phase of our expansion.
12 p.m. Landit Expert Session Webinar with global customer. We host these one-hour webinars as part of our package. Today we’re discussing how to build your personal brand, but we also have a series on how to build your board, how to negotiate, how to take risks, etc.
1–2 p.m. LST Focus Time.
2 p.m. Team meeting. We ask ourselves, “What did we learn this week from our customers that we want to think about incorporating in our product? What’s the feedback?”
3:30–4:30 p.m. Investor update meeting.
7 p.m. Dinner with hubby.
9 p.m. Family ping-pong game!
10:30 p.m. Sleep. It’s been a long but rewarding week. I don’t trust when people say, “Oh, I want to be an entrepreneur”—because it’s really hard. You have to have a bigger mission if you’re going to be willing to run through fire. And I am on a mission: to democratize career success for everyone.