Bootstrapped startups and the shit I learn in therapy

I moved to Detroit from Charleston, SC in June of 2021 and have absolutely fallen in love with this city.

Don't get me wrong, it's obvious how much Detroit has suffered in the past. You can see how much money was once here, and you can tell that most of that money has left. And it has seriously hurt many neighborhoods.

But the people here are friendly and welcoming (when they aren't driving), and there is a creative underdog vibe that I love.

I've described it to friends like this. Your big cities (New York, Atlanta, Chicago) have cool stuff to do everywhere you look. Then after you've been there a while, you start to find a second level of things that are possibly cooler, but a little more hidden.

With Detroit, there isn't as much to do on the surface. But there's a ton to do if you spend a little time looking. Here are my favorite spots so far.


  • Eastern Market: if you're here on a weekend this indoor/outdoor farmer's market is awesome, and there are great food vendors as well (check out the breakfast tacos or the Pierogis). During the spring they have a massive flower sale, although you can find affordable flowers and houseplants any time you're here. There's a great vintage shop in the area too, and one of Detroit best breweries (Eastern Market Brewing) is right down the street.
  • Bell Isle: Massive (~900 acre) park on an island in the middle of the Detroit river. Part of it is a state park with a small fee, the rest is free to access. There's a small aquarium and a beautiful observatory, as well as great views of Detroit.
  • DIA: if you like art the Detroit Institute of Art is free and absolutely massive. The Diego Rivera piece is mind boggling.
  • Dyno Rock Climbing Gym: Dyno Detroit is a rock climbing gym located in the Eastern Market. It's also my favorite place in the city. The community is friendly and welcoming, the climbing is great, and it's near a ton of other cool stuff. You can get a day pass and gear for under $20.
  • Sports: The Detroit teams aren't good... but tickets to a Tigers game are cheap and the view is amazing.
  • Detroit Bus Company: take a tour and support free rides to afterschool programs for Detroit youth
  • The Schvitz: spend an afternoon relaxing between the sauna and the pool with your friends at this old-school health club. It's also BYOB. Check ahead of time, because certain days are men or women-only (Sundays are women-only and they have acupuncture and tarot readings).


The Detroit food scene is highly underrated. It reflects the diversity of the city, and is generally pretty affordable. Definitely set aside some time to explore and eat.

  • Detroit style pizza: Detroit pizza is having a moment and for good reason. It's crispy, cheesy, with an awesome crust. My recommendation is Michigan and Trumbull, and make sure you get the cilantro ranch.
  • Takoi: Amazing, upscale Thai food with a rotating menu and top notch cocktails. This is probably my favorite restaurant, period. Not just in Detroit. I've never had anything here I didn't like. I strongly recommend ordering family style.
  • Supergeil: German doner restaurant. They're owned by the same people who own Two James Distillery across the street so they have lots of cocktails. Get the lamb and beef doner, with the baba ganoush and the fries.
  • Tacos: Despite being across the river from Canada, Detroit's Southwest and Mexicantown neighborhoods have large hispanic populations and some really incredible food. Check out La Jalisciense Supermercado Y Taqueria or Antojitos Southwest. The latter specializes in birria.
  • The Goblin: Sushi. Our favorite, neighborhood sushi restaurant, they do all of the basics really well.
  • Tuhamas: Detroit has one of the largest middle eastern populations in the United States. Visit nearby Dearborn for some of the best middle eastern food you've ever had. Tuhamas is a small carry out shawarma restaurant that will knock your socks off, but there are lots of great options.
  • Baobob Fare: Boabob Fare's African-inspired bowls are absolutely delicious and will fill you up for a super reasonable price. Make sure to try the passionfruit drink or the hibiscus tea.
  • Second Best: Get the fried chicken sandwich and the mac n cheese. Also be prepared, it's loud.
  • Gus's World Famous Fried Chicken: small chain fried chicken place, it's spicy and they serve fried okra.
  • Detroit Shipping Co: modern food-hall, with awesome options including Vietnamese dumplings, Jerk chicken, Thai food (their fried dumplings and pad thai roll are amazing), and New York style halal platters. They also have a great patio area and good cocktails.
  • UFO Factory: dive bar with a tiki bar upstairs and crazy hot dogs (vegan options too) and really good waffle fries.
  • Saffron de Twah: amazing (James beard award winning) Morrocan food. Get the tea, the meat lover's hummus, and a sandwich. The chef comes and sits and talks to everyone who eats there. They also provide above average pay and super competitive benefits to all of their employees.
  • Momento Gelato and Cofee: the dark chocolate gelato is... so good.
  • Cork and Gabel: if you're looking for a great brunch spot check out Cork and Gabel in Corktown. There's never a huge wait, and the German-inspired food is fantastic. They premake loads of cinnamon rolls for brunch so when you order one they'll deliver it to your table in seconds.
  • James Oliver: amazing bagels, although I'm still pissed they got rid of their roasted onion cream cheese.
  • A few more of our favorite spots are Mercury burger bar, Bucharest grill (good local chain), Grey Ghost (great for food or cocktails), Johnny Noodle King, Ima, Green Dot Stables, AlTayeb restaurant, and Frita Batidos.


Most of the places above have awesome cocktails, but here are a few places that specialize in drinks.

  • Batch Brewing: Great outdoor patio, locally brewed bear, and delicious cajun-inspired food. They also have food pop-ups pretty regularly.
  • Eastern Market Brewing: My favorite brewery in Detroit, they don't have food but they have great beer.
  • Valentine Distillery: Their white blossom elderflower vodka is mind-blowing and their house cocktails are fantastic.
  • Two James Distillery: distillery offering tours in Corktown, they also serve amazing cocktails at their bar.
  • Collect Beer Bar: great, local hang out spot with the friendliest bar tender you'll ever meet, an awesome beer selection, and a great rooftop patio.
  • Sugarhouse: you will need reservations to get in, but this place has incredible cocktails. They don't have a full food menu, but they do have truffle popcorn.
  • Cafe D'Mongos Speakeasy: you'll get stiff cocktails, live music, and an eclectic slice of Detroit history at this speakeasy.
You’ve successfully subscribed to Andrew Askins
Welcome back! You’ve successfully signed in.
Great! You’ve successfully signed up.
Your link has expired
Success! Check your email for magic link to sign-in.