A Tale of Two YC Experiences: Lessons from serial entrepreneur John Milinovich

We sat down with John Milinovich, Head of Discovery Product at Clubhouse, to learn how his mindset and startup playbook has evolved between founding his first and second ventures. 

Previously, he co-founded and served as CEO at Aesthetic and URX (acquired by Pinterest). In both cases, John and his early team went through Y Combinator. 

In the first installment of our two-part conversation with John, we dive into: 

1. Growing in between his first and second YC experiences
2. Why founders should seek advice from other founders
3. How finding product-market fit is a dynamic process

"There's no golden egg when it comes to successfully building a company. But there are many obvious failures that a little experience can help you avoid."

The difference between first-time and repeat founders

John's split his career between big companies and his startups.

He started at Yahoo, followed by Google, and then founded his first company, URX. That startup grew to about 40 people before Pinterest acquired it.

John continued at Pinterest, where he was a part of a team focused on building out content and understanding ad targeting systems.

He left after a few years to start a design automation company, Aesthetic, which is still going strong, but John moved on eventually because he was ready to work for a later-stage brand.

He joined up with Clubhouse as their 34th employee and first product manager to work on the discovery side of core product functions. 

He recently switched to leading monetization efforts that'll roll out later this year. 

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What did John do differently with startup #2?

John went through Y Combinator twice. While there, he learned how to avoid mistakes that commonly kill startups. 

He made subtle but crucial tweaks (based on learnings from URX) to his process for Aesthetic. 

1. Relentlessly pursue product-market fit — He deliberately focused on product-market fit ASAP. He had a newfound appreciation for how it feels once your brand has nailed it and knew when it was time to start deploying resources in support. 
2. Fine-tuned instincts — He was more comfortable changing direction, hiring, letting people go, and making other big, difficult decisions. 

"No two companies are the same, but many rhyme with each other. That helped me feel a lot more comfortable with decision-making the second time around." 

Where should early-stage founders turn for tactical advice?

John recommends that first-time founders look to mentors who are on the same track as they are — but three to five years ahead. 

Often, founders look to VCs for feedback, but many VCs weren't founders themselves or have never worked at an early-stage company. They don't have directly relevant experience.

They can offer platitudes and advice for later stages, but that's not what startups need. John notes that the partners at YC had that direct experience, which was super helpful.

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Solid guidance vs. pre-baked solutions

Founders will receive differing advice from people who have built companies vs. those who’ve only ever read case studies about building companies.

That contrast is most noticeable when it comes to advice on product-market fit.

Those who haven't worked at early-stage startups are prone to describing product-market fit as a binary, black-and-white issue. 

In reality, most companies operate in an awkward, in-between gray stage for a long time. 

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Product-market fit is a dynamic state

Many founders quickly learn that product-market fit is something companies can phase in and out of. There’s no single fit for most brands. 

Companies often find multiple product-market fits at different scales and for distinct customers. 

That gray area as your brand works through moving variables is complex. Advice from people who've experienced it will have a subtlety and nuance that blanket advice won’t. 

People with real experience also know that sometimes there's just no advice to be given. Instead, the issue is asking the right questions and forcing the brand to answer them honestly. 

"People who've experienced the early search for product-market fit realize it's all shades of gray and working with the gradations between them."

Key learnings from dual Y Combinator sprints

John had positive, but entirely unique experiences between the two times he went through YC, since the second run built on his knowledge from the first. 

In the summer of 2013, John went through YC with 53 other companies. The program put them in four different groups, but everyone happily interacted. 

John remembers he was "very, very green." His company built their core technology, but they had a dozen ideas about potential uses and weren't sure what direction to go in.

They were searching for the correct path forward and for effective ways to talk to customers about the product, which they developed throughout the program.

He held onto some advice from Paul Buchheit, a Managing Partner at YC and the creator of Gmail: Do the thing that makes you the most money first. 

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YC round 2

During John's second pass through YC, the program had expanded to 250 other companies. Unlike the first time, everyone wound up relatively siloed. 

John compares it to his alma mater UCLA, a large, public school where people tend to stick to others in their same major or department (or, in this case, category or industry). 

He contrasts that with the experience of his private high school: There were only 100 students,  and everyone knew each other — much like his first time at YC. 

John was also armed with far more information this time. His company knew what customer problem it was trying to solve; they now had scope and targeting questions. 

They validated their hypothesis in their second first week at YC. Their first year, it took them half the length of the program to generate actual revenue. 

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Growth vs. distribution: Priorities at different experience levels

From a founder’s standpoint, the education, coaching, and one-on-one time John received were equally valuable both times. 

It’s a testament to how YC has scaled their model. They’ve maintained the same level of intimacy with significantly more brands attending. 

The second time around, John could better appreciate the potential benefit of being in a room with 300 other founders. 

A lot of his closest friends are from that first YC 2013 cohort, whereas the second cohort became many of his first customers. 

He was able to approach his cohort in Year 2 as an almost B2B sales experience, enabling Aesthetic to scale quickly.