Stepping into The Shade Room with Angelica Nwandu

09/20/24 • 62 min

In April 2015, I read an article that elicited a reaction I’d only had a few other times prior.

We had just closed applications for our first round of experimental indie investments and had made most of our selections.

The article in question was titled Instagram’s TMZ, not exactly a title that would typically grab the attention of a Mormon dad in Utah. But I was captivated by the story and the mystery of the founder known only by her first name, Angie. By design, she was not the face of The Shade Room (TSR), that was a distinction for her large and growing audience of “Roommates” who kept the comments buzzing and the scoops flowing.

Any fan of pop culture knows that it's largely downstream of Black culture. Control the headwaters of culture, and you can shape the conversation around it. That’s the opportunity that I saw in TSR, but the risk was that they would follow the playbook of the other modern media giants of their generation - Buzzfeed and Vice. Unlike the latter, who had built their own technology and properties from the ground up, TSR leveraged existing social channels to go directly to their audiences. This was as practical as it was counterintuitive and ultimately led to a meaningful part of the TSR success story, while Buzzfeed and Vice have drifted into obscurity and irrelevance.

A few takeaways from this conversation:

The Shade Room's journey and growth:
Angie started The Shade Room in 2015 with a vision of it becoming influential and a cultural game-changer, despite having only a few thousand followers at the time. After indie's investment, Angie was able to take that confidence and has grown significantly since then. The Shade Room has become an integral part of Black culture and media, with a highly engaged community called "The Roommates".

Angie's approach to building The Shade Room:
Angie has purposefully kept the company bootstrapped, avoiding taking on additional investment in order to maintain ownership and control. She's turned down multiple 9-figure acquisition offers, driven by her long-term vision and purpose rather than financial gain. As a Black media company representing Black culture, The Shade Room faces increased scrutiny. Advertisers have undervalued The Shade Room's audience compared to other media outlets, like BuzzFeed and Vice. But because she kept her independence, the Shade Room was able to outlast those over-funded media companies.

Advice for those starting out:
If Angie was starting the Shade Room today, she'd follow these three pieces of advice —
1) Speak to yourself and your own interests.
2) Listen to your audience.
3) Truly know your audience.

Recording this conversation in Angie’s home was a beautiful contrast to when we first met. Her growth as a business builder and as a person has truly been highlight of my professional career. There’s no doubt in my mind that there’s much more runway ahead for her and TSR. Hopefully that can all happen without landing me in any more diss tracks...

We hope you enjoy listening as much as we enjoyed recording this one.

And as always, if you’re working on something that could be a fit for indie, or know someone who is, don’t hesitate to reach out.B

— Bryce

In April 2015, I read an article that elicited a reaction I’d only had a few other times prior.

We had just closed applications for our first round of experimental indie investments and had made most of our selections.

A few takeaways from this conversation:

We hope you enjoy listening as much as we enjoyed recording this one.

And as always, if you’re working on something that could be a fit for indie, or know someone who is, don’t hesitate to reach out.B

— Bryce

Previous Episode

At Home with Karri Saarinen, Cofounder of Linear

A few years back, I got a DM from a founder wanting to meet and swap stories about adventures in entrepreneurship. Despite being backed by some of the top VCs in the world, they were taking a very different approach from the classic VC blitzscaling playbook. As we sat on the back patio of a bar in Brooklyn, it was clear that how Jori and his founding team at Linear were building was very aligned with how we were encouraging founders to consider building through indie (note - we are, sadly, not investors in Linear).

Years and a Series B later, the Linear founders have continued building their company on their terms.

A few weeks back, I had the opportunity to sit down with Jori’s co-founder, Karri Saarinen, at his home in California for a wide-ranging talk. We covered everything from their time at some of the biggest hyperscalers of the last wave (think AirBnB, Coinbase, Uber), to net-negative lifetime burn rate (they’ve basically never spent the $52M they’ve raised), to their version of “Founder Mode”, to Finnish potato farming.

A few notable takeaways from this conversation:

Building a Different Kind of Company
Linear aims to build a company and product in a way that differs from typical Silicon Valley startups by focusing on product quality and craft rather than rapid scaling. By maintaining profitability and controlled growth instead of burning through venture capital, they’ve been able to build a venture-scale company without giving up optionality. The founders draw on their experiences at companies like Airbnb and Coinbase to avoid pitfalls they observed there, like culture dilution from hyper-growth. They’ve emphasized a small, high-quality team over rapid hiring.

Product and Growth Philosophy
Linear prioritizes product quality over growth hacks or aggressive marketing. By focusing on making the product so good that people naturally talk about it, they’ve been able to capitalize on word-of-mouth from satisfied users as a growth strategy.

Founder Approach
Karri emphasizes the importance of founders staying connected to the product and the craft. Because they care deeply about the output and quality of work, they can avoid creating unnecessary management layers or processes. Karri advocates for founders to think critically about standard startup advice and find their own path that aligns with their strengths and values.

Remote Work and Culture
Linear is fully remote, which they see as an advantage in maintaining focus and avoiding unnecessary distractions like office design. The company emphasizes clear communication and looks for employees with strong communication skills to thrive in a remote environment. Remote works if the founders want it to.

I really loved this conversation with Karri.

It highlights for me that there really is a new wave of ultra ambitious founders who are finding a way to stay true to themselves and their visions by focusing on what matters, and putting themselves in a position to controlling their own destiny. Linear, Vanta, Zapier, Webflow, and so many others are validating that growth at all costs doesn’t have to cost you everything.

I hope you enjoy listening to this conversation as much as we enjoyed recording it.

As always if you or someone you know are working on something that could be a fit for indie, don’t hesitate to reach out.

Next Episode

Career Transitions for High Achievers with Steve Schlafman

Walking through Madison Square Park a year ago, @schlaf talked about transitions, something he knew a lot about.

I first met Steve when he was a junior investing partner at RRE, a venture capital firm in New York City. At the time, Schlaf had the NYC startup scene in a chokehold. He had a reputation for hustling hard and winning some of the hottest consumer deals in the city. He was charismatic, he was aggressive, and then, he was gone.

At first, he left RRE to do a firm of his own, then he joined Primary as a Venture Partner, then struck out on his own again to blend a CEO coaching practice he was developing with a new chapter as an angel investor.

In the park that day last year, he talked about a new evolution of his practice. He'd gone deep on the study of transitions. As someone who'd lived through many in his career, he felt a connection to the subject. As conversations and calls for help with career transitions flooded into his coaching practice, he felt a calling.

That calling is still taking shape, but the current iteration of it is Downshift, a cohort-based "decelerator" for high achievers in career transitions. Downshift gives these strivers a place and permission to slow down and take inventory before embarking on the next chapters of their careers.

Some takeaways from this conversation —

Steve left venture burnt out from the nonstop pace and transactional nature of venture. He wanted more authentic relationships not based on dealmaking. Venture can feel like a “legalized casino” focused on status and wealth generation rather than substance. Instead of constantly being in meetings and pitches, he needed to slow down and have space to think and process.

In hindsight, Steve would approach venture differently:
— Scheduling no meetings before noon to allow time for research and deep thinking.
— Partnering only with people who share similar values.
— Balancing effort and recovery to avoid burnout.
— Being more upfront and decisive with entrepreneurs, trusting his intuition.

As a coach, Steve helps clients navigate major life/career transitions and “ego deaths” as their identities and narratives break down. In practice, that looks like holding space with presence and empathy rather than driving them to specific outcomes, helping them see patterns and make decisions from a place of clarity and agency, not fear, and slowing down to allow emotions to be felt and processed. This method helps his clients reach a sustainable and ultimately stronger place.

The prompt to reach out to Steve was seeing his work show up outside of the usual startup circles, notably Bobby Kim, founder of the streetwear brand The Hundreds. Bobby wrote —

"Maybe it’s just me.

But I keep running into the same conversations around career crisis, purpose, and transitions. Several times a week, I’ll meet up for lunch, sink into a DM, or sift through a Telegram chat, and a friend will confide that they’re experiencing a tough time. When I comfort them, they are surprised that they’re not the only ones struggling with finances, that other industries aren’t immune to existential threats. They sigh relief when they realize that most everyone I know is confronted with formidable questions of their lives and futures."

He goes on to cite Steve's work and relate it to a wide range of industries with a similar theme. It felt like a good time to sit down with Schlaf to dive deep on his work and this current moment.

When I approached Schlaf about sitting down to talk about his journey, he had the vision of filming in Central Park. A daunting request, but one where teamwork really did make the dream work. The visuals were stunning, and the conversation clocked in at nearly 3hrs (don't worry, we edited it down to something much more manageable).

The park lent an incredible vibe. You'll hear notes from a nearby saxophone, people stopping to say hello, birds chirping, and general movement of the city. We really love how this one turned out, and hope you enjoy listening as much as we enjoyed having it.

— Bryce

As always, if you or someone you know has a company that could be a fit for and investment from indie, don't hesitate to reach out.