The workweek of a date-night entrepreneur

Despite a packed schedule, idk tonight founder Jordan Scott says there's 'no downside' to being her own boss

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.

Jordan Scott, founder of idk tonight, a website and newsletter that helps New York City couples make date-night plans, is happy to talk business—but first, she has an engagement story to share. Her boyfriend, Nick, proposed to her three days earlier during a joint family trip to the Bahamas, and she’s still in shock.

“We’re lounging on the beach and I said, ‘You want to go on a walk?’” Nick said he needed a few minutes (he was, in fact, waiting for his sister’s boyfriend, who’d been tasked with surreptitiously photographing the moment), but Scott got impatient and left. Two minutes later, Nick ran down the beach after her. “I was in a bikini, and he brought me my coverup and said, ‘It’s really sunny, I think you should put this on.’ He knew I wouldn’t want to be, like, naked in these pictures.” Their families were waiting with champagne when they returned to their beach chairs. “Everybody was clapping and crying,” Scott says.

This is the sort of intimate look into her relationship that Scott gives every week in her idk newsletter, which includes a personal anecdote, curated New York City date plans, a spotlight on a local couple called #CoupleGoals, and more.

“I loved New York City and loved the idea of creating something that made it easier and more exciting to explore it,” says Jordan Scott, founder of idk tonight.

Scott, age 24, launched idk (which stands for “I don’t know”) in September 2017, about eight months after quitting her first job out of college, an entry-level position at CBS This Morning. “I couldn’t point to any [other] job there that I would want,” she says. Plus, she had the seed of a business idea. “I loved New York City and loved the idea of creating something that made it easier and more exciting to explore it,” she explains. “I just felt like, I’m young. Maybe I take two years to try it, and if it fails I can get another job [knowing], ‘I have all these new skills.’ There was no downside.”

The business started as a concierge service: Users could request a night out, and Scott would respond with plans and make reservations. Soon, she realized “almost every request was from couples. We thought, whoa, OK. We need to totally focus on couples.”

Though idk is an editorial product with about 11,000 monthly unique users and 10,000-plus email subscribers, there’s an app in user-testing right now—with plans to be in beta this year. It functions much like a dating app, only instead of swiping on people, you’re swiping on restaurants, bars, and events—and if your partner’s on the app, too, your picks are added to a joint queue.

In the five days leading up to her holiday break, Scott, a WeWork Labs member at New York’s WeWork 175 Varick St, kept a diary of her workweek:

Monday

7 a.m. Sleep in since Nick has dog-walking duty, then run on the treadmill in our gym upstairs.

8:30 a.m. Out the door of our downtown apartment. Try two new podcasts: WSJ’s The Future of Everything and Gimlet’s Without Fail.

9 a.m. At my desk, organizing my list of priorities. I’m on Week 9 of the Best Self Co. journal, a 13-week sprint with weekly and daily goals—and so far, I’ve finished the clickable prototype of the idk app and gotten our deck into fighting shape.

9:15 a.m. Reach out to a friend for her financial-projections contact. Our projection is about users and growth; it’s less about revenue, at least in the first couple years.

9:30 a.m. All things social, starting with an Instagram Story of our three “featured plans tonight.”

10 a.m. I’m consulting for a startup called Cinch, a digital wallet that rewards users for shopping locally. I run their social accounts, write copy, and help with email. It keeps idk tonight afloat.

11 a.m. Dig Inn for lunch.

11:45 a.m. Add new plans to idk’s calendar. We always have the next seven days of life in New York on the calendar.

12:15 p.m. Research three companies with investors that could be interested in idk. I received a great piece of advice: Research companies that your potential investors have invested in and see which aspects of your company are relatable—then focus on those aspects in your deck.

1 p.m. Get deck into shape to send to contacts. I’ve been grappling with, “Do I do an official friends and family (slash, maybe a little more serious angel) round, or go straight to venture capitalists and say, ‘We have this audience of thousands of couples. Give us serious capital to make this happen.’” Right now, idk is funded with my savings and consulting work.

1:40 p.m. Confirm date-night schedule through mid-January. Our incredible operations intern, Priyanka, has done a ton of heavy-lifting here, and it’s great to be able to just edit/approve. (I employ two interns and six freelance writers.)

1:55 p.m. Pay people. Supposed to do this every Friday, but I’m our entire accounting department. I use Qwil, which I love.

2 p.m. Walk to Joe & The Juice for my favorite coffee shake. (May or may not have stopped into Tiffany’s to try on rings. Since I run a couples-focused company, I feel this is valid.) I’m a bit burned out after an intense morning. Some founders say, “Monday is for marketing, Tuesday is for fundraising, Wednesday is for this.” Right now it feels like, “How far behind are we on the calendar today? Start with that.”

3 p.m. Emails. I write a recommendation testimonial for Petal+Eon, a company that preserves flowers into cool bouquets.

4:30 p.m. Fill out a W-9 for a new relationship column I’ll be writing for What Should We Do! I’m living out my Carrie Bradshaw dreams.

4:45-6:45 p.m. Prep and schedule our glorious weekly newsletter. We’re looking to switch off Mailchimp because we’re paying an arm and a leg, and half of our emails go to spam. SendGrid? Campaign Monitor? Bueller?

7 p.m. Leave the office earlier than expected, which is great.

8-10 p.m. Finish Maniac with Nick; leftover cabbage soup and sushi for dinner.

Tuesday

6:15 a.m. Wake up and head to BTF Bootcamp.

8:30 a.m. Out the door. Listened to Wait Wait…Don’t Tell Me! and stopped at Deb’s for a wrap with egg, cheese, avocado, and home fries.

9:30 a.m. Meet with a new social hire and discuss KPIs like followers and impressions. Still trying to get into a data-first mind-set.

10:30 a.m. Cinch work.

11:30 a.m. Meet with Andy from BucketListers. He runs several “what to do” Instagram accounts, and we’re always swapping best practices. We’re partnering on a Valentine’s Day-focused guide, written by idk tonight and posted on BucketLister’s site. He’s also connecting me with his TodayTix contact so we can continue promoting theater around New York (and use affiliate links so we get paid for it).

12:40 p.m. Send ideas for What Should We Do!

1 p.m. Lunch. Easiest and closest: Just Salad.

1:30-3:30 p.m.

  • Update the idk calendar.
  • Reach out to the former founder of a failed couples’ app—hoping she’ll come on as an adviser.
  • Accept pitches for “date night ride-alongs”—where couples give a behind-the-scenes look at their date night on idk’s IG Stories—from event organizers and restaurants.
  • Send edit tests to prospective writers. Fingers crossed.
  • Apply to TodayTix affiliate program and get accepted within 30 minutes.

4:30 p.m. Leave office to get ready for tonight.

7 p.m. Dinner with Nick at Faro. Best pasta in New York.

8-10:30 p.m. House of Yes Xmas Spectacular with Nick for an IG Story. We’re slowly going out less and less. So many couples are excited about free tickets or dinner that they create the content for us.

Wednesday

7 a.m. Wake up with congestion, a headache, and a sore throat. Uh-oh. An entrepreneur has no time to be unproductive. Stay home for a few hours to work, rest, and gear up for the second half of the day.

9 a.m. Prep our Instagram posts. Can’t wait to hand over social in January.

9:30-10 a.m. Throw in a load of laundry.

12 p.m. Feeling 1,000x better. Get coffee and a wrap at Starbucks.

3 p.m. Head into the office with my dog, Walker.

3:30-5 p.m. Meet with Agility.IO, which built the idk app prototype, to discuss functionality, possible routes for funding, and user testing, among other things. Afterward, I feel super-empowered, enlightened, and armed with a plan.

5:30 p.m. Head home because my entire family is up from Florida. We order food from our favorite Italian place (Pomodoro) and catch up.

Thursday

7 a.m. Rise and shine! Send emails. (Now I have responses to look forward to throughout the day.) Then Signature II at Physique 57.

10 a.m. Go over user-testing results. One couple, Rease and Adam, had awesome insight into the app, and we’ll be making several updates based on their feedback.

11 a.m. Call with a rep for the French restaurant Brigitte. We’ve featured it on the site, and now we’re hoping to get a couple to check it out for an IG takeover.

11:30-1:45 p.m. Cinch work, then a deep-dive of idk’s Google Analytics. This month, 60 percent of our traffic was from Google, 25 percent was direct, 17 percent was social, and 2.2 percent was referral.

2:30-4:30 p.m. At the Entrepreneur magazine office to meet editor-in-chief Jason Feifer and Terry Rice, a digital-marketing consultant who’s heading a new program there. Terry was my digital marketing instructor at General Assembly in 2016, and he encouraged me to try out for Entrepreneur’s competition to be on season four of Elevator Pitch—and I won! I fly out to L.A. in March to shoot it.

6:15 p.m. idk tonight holiday party at Lazy Point.

Friday

8 a.m. Working from home. Nick cooks us a delicious breakfast of eggs, bacon, and hash browns. I go out in the rainstorm for coffees and discover something amazing: Starbucks Iced Blonde Cold Foam Cappuccino.

9 a.m. Social, Cinch work, and pack for Christmas. Then update the idk calendar and site as much as I can so I don’t have to look at a screen over the holiday.

12 p.m. Pay people! On time. Good job, me.

12:10 p.m. Start writing the What Should We Do column.

2 p.m. Good call with someone who is potentially doing our financial projections.

2:30 p.m. Begin making an outline for our plan for February. Questions I’m asking myself:

  • Take a look at the V-Day Guide from last year: How can it be revamped?
  • Who can we make deals with again?
  • What numbers can we show them to represent our growth?

3:30 p.m. Schedule all of social (both for idk and Cinch) through New Year’s. Insanity.

5 p.m. Officially starting the holiday week!

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