Lucky Sweater

Tanya Dastyar and Carley Lake both care about community and sustainability... a lot. They care about building a great product, building a great company, and making a positive impact in the process. This shared ethos enabled them to zero in on one another while they were both at On Deck. Propelled by their passion (and complementary skill sets), they brought slow fashion startup Lucky Sweater to life. The company believes in more sharing and less buying, more hanging out and less feeling alone. Those are the values that Lucky Sweater’s co-founders built their relationship on, too. 

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How and when did you two first meet? 

Carley: I was looking for a co-founder when I first joined On Deck. I reached out to a lot of people in the community with technical and program management backgrounds, and sustainability and/or secondhand consumption interests. I ended up messaging Jake Singer, Tanya’s boyfriend, because he mentioned in his On Deck profile that he was interested in sustainability and composting. We had a great chat and he mentioned Tanya and how she would probably be interested in learning more. I emailed her that day.

Tanya:  My partner Jake was excited after a call with Carley, and said he wanted to connect us. I had no expectations going into the call. I remember, it was right after Carley turned 30. Not sure why that’s stuck in my memory.

Carley: Yes! November 2020. A big month for me—a new decade with a soon-to-be co-founder! We started working together and building asynchronously. We finally met in person in July 2021. 

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How did you know your co-founder was “the one”?  

Tanya: I was hit with the realization that Carley might be someone who excelled at all my weaknesses – and then some! She was so incredibly confident. I was impressed by her unique insights, passion for the space, and how much she’d accomplished on her own up to that point. We both were excited about this niche space, and it felt right. With deeper conversations, we discovered we both hoped to build a sustainable company.

Carley: I remember right off the bat I thought Tanya was positive and optimistic. She was confident in herself and her skills. I was also so impressed that she built a career in tech and product management while following her design, UX, photography, and other creative passions. We filled in the “50 Questions to Explore with a Potential Co-Founder” and it was clear we were aligned on what type of company we wanted to build and that our skill sets were really complementary.‍

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Is the experience of having a co-founder what you expected?

Carley: I never thought I would find a partner just as much into the mission, vision, community, and product as I was and would continue to be, but I found that in Tanya. And as much as I wanted a co-founder, I don’t think I realized how important and necessary it would be to have one. We make each other better leaders and continue to have hard conversations about product changes, runway, and hiring. We came from two very different types of tech companies, Uber and Microsoft, each at different parts of growth and scaling. Not only do our skills complement each other, but our career backgrounds do too. 

Also, who else is going to send me a bottle of red wine when I'm in the middle of our fundraise?

Tanya: I truly didn’t know what to expect. I wasn’t particularly interested in staying in the tech field when I first met Carley, and was on a mission to work for a company I believed in, for a great mission and purpose. After meeting Carley, I knew I wanted to build this company with her.
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I don’t think I would be a solo founder after this experience. There are infinite things to do as a founder, and being able to share the good and bad times with Carley, bounce ideas off her, and have her be equally invested in the outcome is crucial in the progress we’ve made together. – Tanya‍

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What helps you navigate disagreements?

Carley: We have a supportive group of investors who help us with hard strategy and product decisions. We also both go to business coaches who give us the space to work on developing our leadership skills and strategies for how to navigate hard discussions and disagreements.

Tanya: I think we both use time as a tool when we have disagreements too. We may have a disagreement that we’re not able to resolve at that moment during a meeting, but we always make sure to follow up with a conversation to resolve whatever it is. Time lets us reflect on the conversation, and each other's arguments, and hash things out when we’re in a more neutral and thoughtful position.

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How do you two communicate?

Carley: We meet as a team every day for stand-up. Tanya and I do 1:1s every other day with different goals for each so we make sure we handle day-to-day tasks, while also focusing on long-term goals and vision. 

Tanya: We have also set up a few different channels in Slack, depending on the topic and the urgency of the response needed. We collaborate on feature work asynchronously via Linear and Loom, which works quite well for us. 

What advice would you give someone looking for a co-founder?

Tanya: Look for someone who has a strong talent, skills, and experience in one crucial area, but can still be a jack-of-all-trades. The best skill is finding someone who can jump into a new space knowing nothing and come out an expert.

Carley: I think it is important to think of your co-founder as someone who is inspiring and visionary and can rally others around the company's vision. Will they be able to recruit and inspire top talent to work here? Can they lead teams and a company? Can they not just build a company, but a culture? 

How far do you think you could get on your own?

Tanya: I found the mission I want to build for, the company I want to grow, and the co-founder I want to do it with…if I didn’t have all three of those things, I definitely would not have been a startup co-founder right now.

Carley: I don’t want to even think about having not met Tanya. Next question, please! 

Do you celebrate work anniversaries or milestones together?

Carley: Yes! We love celebrating and taking time to do fun activities together. We’ve done an Airbnb online magic show experience, spent time together at team off-sites in DC and San Diego, ordered surprise treats, and gifted Cameos from reality stars. We also enjoy designing and updating our Zoom backgrounds to celebrate any occasion.

Tanya: I’m still in awe of the virtual magic show Carley set up for our founding developer, where the magician spelled his name out in cards out of nowhere.

What does success look like for you?

Tanya: Building a product that actually solves a user's needs. For us, building a platform that creates genuine connections between people who would have never found each other if it weren’t for the platform. Also, a place where all can express their creativity however is enjoyable to them, while reducing new waste that is created.

Carley: What Tanya said! I want everyone in the world to one day say “Hey, I need XYZ! I’m going to see if my awesome community on Lucky Sweater has it!” before they go to any online site to buy something new. It will be a no-brainer.

Connect with Carley and Tanya, and check out Lucky Sweater‍