Afleveringen
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Todayâs conversation with Mike Salguero went in a direction I really wasnât anticipating. Initially, I was interested in talking to Mike because heâs lived multiple lives as a Founder.
First, buying and then raising 10s of millions for a crafts persons marketplace called Custommade.com. Then, after winding down Custommade, starting what he would term a âhobby businessâ to recover a bit from the toll a large âventure scaleâ swing took on himself, his health, and his family.
Interestingly, the big swing didnât work. But the less ambitious âhobby businessâ has grown to $500M+ in revenue with zero outside funding.
In our Indie Era of Startups talk, we theorize that:
â WE'RE ABOUT TO SEE THE BIGGEST CLASS OF SV-EDUCATED FOUNDERS IN HISTORY
â THEY'LL BUILD INDEPENDENT, INNOVATIVE BUSINESSES THAT WILL CHANGE THE WORLD
â THESE FOUNDERS WILL LOOK FOR MORE FLEXIBLE, SUSTAINABLE, AND ALIGNED FUNDING PARTNERSMike is a great example of those ideas personified, along with Alan from last week's video. The movement weâre building indie to support is happening, and Mikeâs experiences and lessons learned are emblematic of many returning venture backed founders and early employees.
Some other takeaways from this one:
The power of constraints â Mike built a $550M empire on just $10K, proving you donât need hoards of VC cash to disrupt an industry. The constraints he placed on the business early allowed ButcherBox to maintain control and focus on long-term growth rather than chasing short-term metrics to please investors.
Work-life balance isnât just fluff â Mike built ButcherBox while prioritizing taking care of his body and his growing family. This approach demonstrates that success doesnât always mean sacrificing personal well-being, and can actually lead to more sustainable growth and better decision-making.
Playing the long game â With a 25-year vision, ButcherBox is aiming for iconic brand status. This long-term perspective allows the company to focus on transforming the meat industry and building a lasting legacy rather than seeking quick exits or short-term gains.
The âbarbell strategyâ is pure hiring gold â Pairing fresh grads with industry vets creates a powerhouse team. As a VC backed founder, he was pushed to hire the most pedigreed and impressive over the most experienced or most hungry. This unique barbell approach combines the energy and fresh perspectives of young talent with the deep experience and mentorship capabilities of seasoned professionals.
Doing things you canât at a VC backed Startup â When Mike said âhit our goals, weâre going to Mexico,â the team crushed it. A VC run board would have shut down the idea as not worth the significant expense but he was able to deliver on his promise even when it hurt the wallet. This commitment to following through on promises, no matter the cost, has built a culture of trust and motivation within the company.
The final, and I thought most interesting, takeaway from this conversation was Mikeâs idea that companies know what they want to be. Finding and being true to that has been the key to his success and ignoring it was the foundation of his failures.
With Custommade, he wanted it to be something it didnât want to be â a massive marketplace for craftspeople to connect and transact. What it wanted to be was a simple listing service.
With Butcherbox, Mike wanted it to be a hobby business so he could outsource everything and collect a check every month from a beach. But what the business wants to be is a force within the world of meat for better quality products and more humane treatment of the animals and land.
In both cases, and in different ways, heâs fought what the company is telling him about what it wants to be. When heâs embraced his role as a steward for an idea, a business and a culture that will continue long after heâs out of the day to day grew.
Thatâs what I took away from this one. Iâm curious about your take away from this one, too.
Letâs try something new this week â leave a comment on the YouTube video with your takeaways or thoughts, and any experiences youâve had that relate to what Mike shares. Donât hesitate to call BS if thereâs something you think he or I miss the mark on.
Iâll be monitoring and responding to as many comments as I can. Hoping this will be a fun addition to our weekly tradition of sharing these conversations and artifacts with you.
As always, I hope you enjoy listening and commenting as much as we enjoyed recording this one.
And if youâre working on something you think could be a fit for an investment from indie, please reach out.
â Bryce
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Zijn er afleveringen die ontbreken?
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"Would you be mad at us if we raised more money?"
That was the text I got late one night from Will Pearce, co-founder and CEO of Dreadnode, a company we'd funded about nine months prior.
I'd gotten to know Will through a cold DM he sent me. The DM had nothing to do with tech or investing, just starting a conversation. At the time, Will was working at NVIDIA as an AI red team lead putting him at the cutting edge of AI and ML security. As we got to know each other, it was clear he had a large vision for where the puck was going for the broader market and where his expertise and insights could create the foundation for building the leading company for offensive AI security.
I offered to put together a small round to put he and his co-founder, Nick Landers, in business. We filled the round out with several value-added angels and were off to the races to build product and company with indie ideals at the core. And it worked!
Within months, they were signing contracts with the top names at leading research labs and hyper-scalers. On several occasions, they were even profitable! And then the VCs noticed.
Shortly after our round closed, the word started to spread on what the team at Dreadnode was building. Then the emails started. The early answers were nos and not interested, but as demand from customers grew and incredible, early potential team members started coming out of the woodwork, these high class problems were becoming very real problems.
The team found themselves turning away customers and potential hires as their demand outstripped their resources. Thus, the late night text.
The text led to a conversation that led to a formal fundraising process and ended in the announcement last week of Dreadnode's $14M Series A led by Decibel, a top tier firm focused exclusively on security.
In today's video, we unpack the conversation and process that unfolded after that late night text. We dig into why Will may have had concerns that I, and indie, would be upset or not supportive of their decision, and learnings from two very green and very technical first time founders getting sucked into their first proper fundraising process.
I hope what comes through in video is something I've written often â we are not anti-fundraising. But we believe that the best way to improve your odds of building a generational company that can attract world class customers and investors is to focus on the former, the latter will come. And when they do, you'll be in a position of ultimate optionality that empowers founding teams to pick exactly the partner they want, on the terms they want, and get back to build the company they want.
It seems obvious, but it runs so counter to the advice and examples that get celebrated in the startup world. In the case of Dreadnode, they were able to do just that â work with the partner they wanted on the terms they wanted. And, as an added benefit, they were effectively able to skip 2 or 3 interim rounds of funding and skip straight to a fully baked Series A.
Our goal with today's video was to put some personalities and experiences to that narrative and I think it comes through here. As always, I hope you enjoy watching it as much as we enjoyed recording it.
PS â if you see any of yourself in the Dreadnode founders, don't hesitate to reach out to discuss what you're building and whether indie could be a fit for you too.
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It is incredibly rare to have your startup become a verb. Google and Uber immediately come to mind. But what about when a group of strangers or friends with shared interests decide they want to get together? They, Meetup.
Scott Heifferman didnât set out with becoming a verb in mind but he certainly started Meetup with the intent of building something big and impactful. And on those dimensions he delivered in spades. Along the way he sold 30% of his company for $1M to Tim Draperâs DFJ (funny story around the 36 min mark), raised from other great investors (Brad Burnham from USV makes a cameo in the video), met face to face with Mark Zuckerberg who also decided that getting groups of people to meetup would be important for Facebook too, going so far as to run their very first Super Bowl ad promoting their meetup competitor product. There are so many great stories and anecdotes in this one.
In our effort to mine Web 2.0 ideas and playbooks for applicable lessons for this current wave to startups, this conversation delivers in spades. A few take aways:
â The Origins of Meetup and Community Building: Heiferman reflects on how 9/11 and experiences like Burning Man inspired Meetupâs mission to foster real-world connections. He emphasized the importance of creating tools that empower people to form communities and build belonging offline, using the internet as a catalyst.
â Early NYC Tech Scene vs. Silicon Valley: Heiferman shares stories of the scrappy, experimental nature of the 1990s NYC tech ecosystem, contrasting it with Silicon Valleyâs more established infrastructure. He recalls starting iTraffic with maxed-out credit cards and seeing startups like Razorfish and DoubleClick shape the local scene.
â Facebookâs Competitive Threat: Heiferman recounts how Facebookâs groups feature directly competed with Meetup, even running Super Bowl ads mimicking its concept. This competition influenced his decision to sell Meetup to WeWork, as Facebookâs scale and resources were hard to match.
â Critique of Modern Marketplaces: Heiferman critiques platforms like Uber and DoorDash for extracting excessive margins from workers and businesses. He advocates for a fairer market economy where technology empowers individuals rather than exploiting them.
â Future Vision and Lessons Learned: Looking ahead, Heiferman expresses interest in building impactful projects outside traditional VC structures. He emphasizes the need to focus on creating products that energize people, deliver value, and prioritize meaningful societal impact over maximizing profits.
One thing that especially stood out to me in this conversation was a reminder of how âpeopleâ were so core to Web 2.0 ideals. Whether it was getting people to connect online or off, fostering real and personal connection was such an important driver for innovation at that time. When todayâs headlines are so filled with stories that seem to pit people against algorithms, Scottâs sentiment is a refreshing reminder that technology at itâs best is a tool for enhancing our lives, not eradicating them.
On that theme, a comment Scott made has been rattling in my head ever since. At around the 40 min mark he says something along the lines of âAB testing is the price you pay for not having a pulse on peopleâ. In this conversation he talk a lot about energy, following the energy of individuals and his own energy and interests. He seems energized to build again and we talk a bit about whatâs next for him and how his time working in an Amazon warehouse informed his thinking around what problems he wants to tackle. We canât wait to see where he goes with all that energy.
This was a ton of fun to connect with Scott and Brad to revisit the Meetup story. We hope you enjoy listening as much as we enjoyed recording it.
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This is a spicy one! đ¶ïž
This week we sat down with Brandon Arvanaghi from Meow.com to discuss his journey from money burning crypto company to profitable fintech. His tweet last year about hitting the profitability milestone had some obvious, and some less intuitive, take aways from their experience. Everything from opting out of the VC treadmill to applying the Costco model to low margin financial services.
Some other key takeaways:
- Brandon built Meow to $1B+ in assets with just 12 people by rejecting Silicon Valleyâs âgrowth at all costsâ playbook. His secret? Being profitable and savage about staying lean. âThe future is lean - you canât go from 1000 people down to 10 and pass back savings, but you can stay lean from the start.â
- Brandonâs building Meow like âCostco for financial servicesâ - focusing on rock-bottom prices and passing savings to customers vs the typical VC-backed approach of sneakily raising prices to hit growth targets. He believes in 5-6 years, when pricing becomes fully transparent, this will be the only way to compete.
- âVCs are lemmingsâ â Brandon says the 18-month runway advice is a psyop to keep founders dependent on VCs. He argues most VCs just follow each other and care more about looking good to their LPs than helping build real businesses. The rare exceptions? Maybe 1 in 20 VCs.
- âStay in the game, win the gameâ - Brandon argues real innovation doesnât require betting on non-existent markets. His advice? Pick obvious bets without market risk, stay profitable, and make them 10x better through execution. âHow can you not make a generational outcome if you just keep pushing the ball forward?âBig thanks to Brandon for really going there with us. He shares lived experience around many of the ideas we've been advocating for at indie for years. To see someone so fully embrace those ideas and find incredible success on the other side is great validation for others wishing they could go their own way too.
We hope you enjoy listening to this one as much as we enjoyed recording it.
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Late last year, we sat down with Eric Ries, who fundamentally changed how we think about building startups through The Lean Startup. Only Eric can make corporate governance sound poetic. The conversation took an unexpected turn as we delved into what Ries calls "vampire founders" - leaders who feel immortal yet isolated, watching employees come and go while they remain eternally at the helm. This phenomenon stems from founders conflating their identity with their companies, leading to a uniquely lonely experience that differs markedly from traditional CEO roles.
The discussion revealed how the current startup ecosystem, flush with capital but short on genuine opportunities, has created a pressure cooker environment where founders often compromise their original values to fit institutional expectations. Ries argues that most entrepreneurs start with genuine idealism but get caught in a system that strips companies of their distinctiveness - what he calls being "surgically deboned". This process happens gradually through what Ries terms "gravity," where financial transactions unconsciously transmit values that pull companies toward conformity.
Perhaps most provocatively, Ries challenges the fundamental premise of shareholder primacy theory and suggests that the way we currently build companies is neither inevitable nor optimal. He points to examples like Anthropic's Long Term Benefit Trust as evidence that alternative governance structures can work, while arguing that the current system's defenders spend inordinate energy convincing everyone that the status quo is inevitable - a sure sign, he suggests, that it isn't.
Some key insights from this video:
- The "vampire founder" phenomenon describes leaders who feel immortal yet isolated, watching teams cycle through while they remain unchanged
- Most founders begin idealistic but face systemic pressure to conform, leading to companies losing their distinctiveness over time
- The startup ecosystem has more capital than good opportunities, creating pressure to grow at unnatural rates
- Traditional governance structures often force unnecessary compromises that make both founders and companies weaker
- Alternative governance models exist and can work, but the system actively resists their adoption becoming widespread
- Financial transactions always transmit values unconsciously, creating a gravitational pull toward conformity
- The current startup system is defended not because it's inevitable, but because it's actually quite fragile
- Most founders who achieve financial success still end up deeply unhappy due to the compromises they made along the way
- Building trustworthy companies is actually more profitable than exploitation, but the system makes this hard to see
- Change is possible - Ries points to how The Lean Startup went from radical idea to conventional wisdom in just a few years.
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Making any kind of time bounded predictions about where AI will be in the year of our lord 2025 is a fools errand. But, weâre suckers for this stuff, so we asked Jackie from Tribe to revise the State of AI download we did last year and orient it to what she sees coming for AI in the enterprise in the new year.
No sooner did we record the conversation than OpenAI announced Stargate, Operator, and Deep Seek shot to the top of the App Store. And made the whole conversation form the week before feel dated.
But dated is different than timeless and I think what Jackie does an incredible job doing is anchoring founders and executives on the timeless principles of leveraging AI to deliver ROI and unlock entirely new experiences.
For this conversation, the key takeaway is that AI implementation is moving from theoretical to practical, with clear winners emerging based on their ability to drive real business value rather than just run experiments.
-The AI vendor landscape is shifting from a winner-take-all market to a more competitive space, with Anthropic emerging as a serious challenger to OpenAI. Companies are increasingly comfortable switching between different AI models based on specific needs and cost considerations.
-Three areas showed clear product-market fit in 2024:
Enterprise ChatGPT implementations
Customer support automation
Code generation tools (with Google reportedly generating 50% of their code using AI tools)- Many companies are stuck in âPOC Purgatoryâ - running small AI proof-of-concepts that never scale to production. The successful companies are those making real commitments and showing patience through initial iterations.
-The biggest barriers to AI adoption arenât technical - theyâre cultural and organizational. Senior engineers and executives often resist AI tools while junior staff embrace them. Success requires leadership commitment and openness to changing how work gets done.
- Private equity firms are emerging as surprising AI innovators, focusing on implementing AI in their portfolio companies to drive value. This is shifting PEâs reputation from financial engineering to technological transformation.
- âAgentsâ are becoming the dominant theme for 2025, with companies seeking to automate entire workflows rather than just individual tasks. Thereâs growing demand for âfactories of agentsâ that can scale automation across organizations.
- The traditional lines between software and services companies are blurring. Service-heavy companies like Palantir are being valued more like software companies as they demonstrate scalable AI implementation approaches.
- Marketing automation is emerging as the next major AI opportunity, with companies seeking to both reduce costs and improve ROI through automated content creation and campaign optimization.
- Companies that donât move beyond experimentation risk falling permanently behind, as AI is compressing innovation cycles and creating growing gaps between leaders and laggards.
This was a wild ride of a conversation with someone whoâs in the trenches with a wide range of enterprise customers. Her perspective and insights are invaluable. I hope you enjoy listening as much as we enjoyed recording it.
And if you are looking to get started with or level up AI within your company, donât hesitate to reach out directly to Jackie at [email protected]. 600+ of the best AI engineers on the planet are standing by.
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On my flight to NYC last week, I casually asked if there were any events happening in the city while I was there.
Reggie, who you may remember from his New Hardware video, and as the person who coined the term âindie-pilledâ, replied that we should do one of our own.
So we did.
Thankfully we had our cameras in tow and were able to record the conversation. It turned into a nearly 2hr Q&A on all things indie, the current state of venture, the evolution of seed, the role of secondaries in venture, and some funny untold indie lore.
In the video, Reggie mentions a piece he recently wrote titled âLies My Teacher Told Meâ, which set some timely context for this event.
From the essay:
"The point of this is short. The new thing has to look like the new thing, which makes it hard to pattern match to the previous new thing. But pattern matching is at the heart of de-risking. This creates a weird loop of advice.
The previous advice of zero interest rates and Snapchat as the last big thing for consumer software was to grow at all costs / monetize later / find novel behavior.
Nikita Bier showed all of this was wrong with Gas App. Monetize directly in the V1. De-risk through known behavior. Growth inputs must be advantageously proportional to the monetization in the V1.
There wouldnât be a single VC that could share this advice. As a result, weâve only had 1 US consumer internet win since Snapchat."
My sense is that thatâs why indie is resonating so strongly this time around. As we wrote in our FACTS section:
"The game has changed. ZIRP-era playbooks of VC treadmills, pump and dump schemes, and growth at all costs have aged like milk. The future belongs to real builders, building real businesses.
Thereâs a time-tested playbook for building generational companies â less time fundraising, more time building, with a focus on the fundamentals. Most of the iconic companies of the past, think Amazon, Microsoft, and Google as well as emerging leaders like Midjourney, Vanta, and Zapier, have followed a similar playbook.
Weâve built our firm from the ground up with this playbook in mind."
This is the future weâre been building towards, and it seems to be hitting an inflection point.
Thanks to Reggie and the team at Earshot for hosting us and making this happen on short notice.
Hope you enjoy listening as much as we enjoyed having this conversation.
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Chris Anderson canât talk a lot about what he is up to these days. At least on camera.
His LinkedIn profile says heâs currently an Engineer at âStealth". Prior to this current professional opacity, he was at Kitty Hawk, the electric aircraft maker founded by Sebastian Thrun (legendary Stanford Professor and former lead of Googleâs self-driving car team that led to Waymo) and backed by Google Co-founder, Larry Page.
I became familiar with Chris while he was leading Wired Magazine as Editor-in-Chief. His work there was groundbreaking and set much of the pace, tone, and agenda for the early days of Web 2.0 and the Maker movement. After seeing a TedX talk about a side hustle he had selling cellophane bags of electrical parts and open source autopilots for DIY Drones I slid into his DMâs.
There is a lot of buzz around drones today, but note the date on that DM â November 3rd, 2010.
Little did I know at the time, that this little drone business was just beginning to grow from Chris and his kids packing orders at their dinner table to a proper manufacturing and distribution center along the border of Mexico.
As things happened, that DM turned into a conversation that turned into an investment in a company, 3D Robotics, that took Chris away from Wired and into the uncharted worlds of manufacturing, consumer hardware, and defense tech. He was early and 3DR didnât play out the way that weâd all hoped but it laid the foundations for much of what heâs working on now â even though he canât talk much about that publicly.
To say Chris has a knack for living in the future would be a massive understatement.
In this conversation we unpack his process for exploring possible futures â spoiler: Chris has started writing science fiction as a way to explore complex technological implications. He writes a book a month, using fiction as a computational tool to play out scenarios with artificial agents and see where they lead. We get into what he got right and what he got wrong about drones specifically and defense tech more broadly. And we discuss the culture of Silicon Valley, where we spar a bit on the amount of waste and wandering built into the system that ultimately leads to so many unexpected breakthroughs.
Since that first DM, he has become a dear friend, coconspirator, and sounding board for me. The unedited conversation here went on for nearly 3 hours (which reminds me that we really do need an âindie uncutâ channel) but thatâs the kind of person Chris is â generous in sharing his time, ideas, and insights.
I hope you enjoy listening as much as we enjoyed recording this one.
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Soleio Cuervo is more than a chin on the internet. Heâs more than an early design leader at Facebook and Dropbox. And he's more than an epic angel investor.
Heâs a truth seeker and truth teller. Or at least the truth as he sees it.
Soleio was one of Facebookâs earliest designers, joining in 2005 when the company was still finding its identity. During his six-year tenure, he helped shape Facebookâs culture of âmove fast and break things,â where mistakes were acceptable but slowness was not. This philosophy was crystallized during the controversial launch of News Feed, which showed that transformative products could succeed despite initial user resistance if the team moved quickly to address concerns.
After Facebook, he joined Dropbox, first as an angel investor, then full-time in 2012 to lead design when they had just a handful of designers. The transition revealed stark cultural differences - while Facebook was a paranoid, competitive insurgent focused on speed, Dropbox prioritized reliability and stability, aiming to build âspace shuttle quality software.â This experience taught Soleio how company culture gets set early and is deeply influenced by the business model and foundersâ personalities.
Following his operational roles, Soleio had great success an angel investor before building Combine, a hybrid venture firm and design studio. However, the âHappy Mealâ approach of bundling investment and services proved too complex, creating role confusion when advising founders. He ultimately returned to angel investing, finding it provided more authenticity and freedom to give direct advice without the constraints of managing outside capital. His investments include Figma, Vanta, Vercel, Replit, Perplexity, and many more.
The parts of this conversation I find myself continuing to reflect on are just how formative company cultures are and how often that's taken for granted by otherwise overwhelmed entrepreneurs. In our first post about indie we wrote:
Like cement, the cultural foundation for new projects and companies sets early. Those who focus on raising outside capital and achieving fundable milestones have a very difficult time getting off that VC treadmill.Those who focus on creating value for customers and generating positive cash flow from the very beginning are able to make their own decisions independent of competing outside interests.
This is true of fundraising, product, and execution. As Soleio says so eloquently in this conversation - Culture is the deepest moat one can create.
The "culture of Soleioâ seems to contain a bunch of contradictions â care for craft with an obsession for speed. A clearly massive ambition coupled with a desire to be a âtrim boatâ that can be lean and focused.
With Soleio, you canât spell culture without CULT, and in this conversation, he mentions a piece of writing that had a profound impact on him that we would be remiss not to share here:
The Cult of Done Manifesto by Bre Petis and Kio Starks
There are three states of being. Not knowing, action and completion.
Accept that everything is a draft. It helps to get it done.
There is no editing stage.
Pretending you know what you're doing is almost the same as knowing what you are doing, so just accept that you know what you're doing even if you don't and do it.
Banish procrastination. If you wait more than a week to get an idea done, abandon it.
The point of being done is not to finish but to get other things done.
Once you're done you can throw it away.
Laugh at perfection. It's boring and keeps you from being done.
People without dirty hands are wrong. Doing something makes you right.
Failure counts as done. So do mistakes.
Destruction is a variant of done.
If you have an idea and publish it on the internet, that counts as a ghost of done.
Done is the engine of more.
You may be piecing together a theme here that I hope comes through loud and clear here.Accelerating your time to done is the ultimate informant for whatâs next. If you can master that loop, youâre well on your way to having the impact in life and culture that you aspire to.
This conversation with Soleio is a good reminder of that, and I hope you enjoy listening as much as we enjoyed recording it.
Happy New Year!
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Throughout the first year of indieâs return, Iâve felt a real sense of tension.
That tension sat at the intersection of what indie was and what indie wants to be.
In its earliest days, indie was often framed as an anti-VC, profit maxi path. Rigid in its philosophy and dogmatic in its practices. This positioning served as a counterbalance to the investor-focused narratives at the time of "always be raising" and building towards the next fundable milestone.
We had a point to make, but the point was often overshadowed by an undercurrent of disenfranchisement from various corners of founderdom.
So what was the point?
In 2017 we wrote:
We want to enable a world where founders donât need permission from an increasingly small group of fickle funders to exist. We want to see companies thrive that live more than 30 min from Sand Hill Rd. or San Franciso. We want to see entrepreneurs who donât look like, talk like, think like, or see the world like they do achieve their full potential. We want a world that isnât simply trying to get in front of the product road maps of Google, Facebook, Amazon, or Microsoft.Thereâs a wild, weird, and wonderful world of opportunity that will go unrealized if we continue running the current VC-backed startup playbook of asking permission to exist every 12â18 months.
In 2018 we wrote:
The Basecamp way is NOT to never raise money or dogmatically bootstrap a pure and independent business even if it means putting your, or your familyâs, financial well-being at risk. No, the Basecamp way is to put yourself in a position that should you choose raising money is in your best interest that it can be done on your terms and on your timeline and embody your own definition of success. And, far more founders should follow it.In 2019 we wrote:
âWeâre not anti-V.C.,â said Akshay Kothari, the Notion's chief operating officer. âWeâre just thinking for ourselves, rather than for them or other peers.â The rules of engagement around investment are changing as quickly as the dollars are shifting to various stages for deployment. Retained ownership and optionality are slowly replacing amounts raised and artificial valuations as the ultimate signal of ambition. If youâre an investor or entrepreneur not taking notice of these changes youâll be left flat-footed in the months and years to come.Hopefully, youâre starting to see a pattern.
Historically, we anchored on fundraising to tell that story. But I think weâve hit the expiration date for that.
Indie was never about fundraising. It was, and is, about independence. Not having to rely on outside funding just to exist is one way to do that. Not having to ask anyone for permission to build the thing you can't not build is another. But I'm excited to start telling other dimensions of what this "indie era" has in store.
As Iâve been telling the indie story this year Iâve continued to feel the tension between the old indie and the path ahead. Trying to square what people wanted indie to be and what it wants to become.
As a final send-off to the old indie, we recorded a little video capturing some of the ups, downs, and a hahs of the journey so far. It was surprisingly cathartic to recount the indie lore and felt like a proper end to the new indieâs first year.
2024 was an incredible year for indie generally and for me personally. I canât thank all of you enough.
â Bryce
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Once upon a time, when MTV played music videos, their more mature sister channel, VH1, had a show called âWhere Are They Nowâ. The idea behind the show was to track down notable artists of previous generations to see where life had taken them once theyâd stepped out of the spotlight.
OK boomer, what does this have to do with the indieverse specifically, and the culture of technology more broadly?
In most creative fields, whether it's art, fashion, architecture, etc., there's a deeply held sense of respect, even reverence, for the innovators who came before. The breadcrumbs of insights and artifacts or creation serve as a foundation of reference points for those who come after.
But tech, as a creative field, feels different. Always forward, never back. There's frequently disregard, even contempt, for the innovators who came before.
I often say we have the raw materials for any number of possible futures. Breakthroughs in AI, energy, chip design, crypto, biology â the future has never been brighter. As excited as I am to charge forward, I thought it would be valuable to look back.
When I entered the venture market, it was in the wake of the dot com crash. Shortly after, my partner, Tim, popularized the term Web 2.0. Then, as now, there was a deep sense of hope starting to swell in technology. There were lessons to draw from and infrastructure to leverage to build upon, in addition to a renewed sense of optimism for the role technology could play in our lives.
As we enter a similar moment in tech, I wanted to return to some of the innovators of Web 2.0 to see if there were any lessons to glean from their experiences, and to celebrate their contributions to the progress we're building on now.
The first of these came up in our conversation with Charles from Are.na earlier this year. He and his team and had drawn inspiration from a popular Web 2.0 called Del.icio.us, known primarily as a shared, social website bookmarking service. I have known and respected its founder, Joshua Shacter, for years. We decided to trek to Mountain View for a catchup with Joshua on his past learnings and current projects.
Joshua built Del.icio.us as a side project while working at Morgan Stanley, evolving it from his earlier project called Meme Pool. He didnât set out to build a startup - it was simply a tool to manage his own bookmarks that grew organically to millions of users. Within less than a year of raising funding from Fred Wilson at USV, Del.icio.us was acquired by Yahoo, where Joshua experienced the challenges of corporate bureaucracy and struggled with the loss of control over his product.
The Web 2.0 era allowed for more experimental approaches, whereas todayâs entrepreneurs are highly focused on specific business opportunities, particularly in areas like AI tooling for business functions. Joshua believes that the current AI revolution has reset computing to a pre-6502 type era where fundamental architectures are still being determined, making it an exciting and challenging time for founders who need to balance innovation with market demands.
When investing, Joshua looks for founders who are perpetually unhappy with their tools and constantly seeking improvement. He prefers to invest in weird ideas that make him think, âI never would have thought of thatâ, rather than incremental improvements to existing solutions. His approach is fundamentally engineering-driven, and he values founders who can engage in deep technical discussions.
This one was a ton of fun. It's a new format for us, so be gentle with the feedback. Weâve already learned so much and hope to improve on it. We have a few more of these in the can and a few more lined up for the new year. If thereâs someone youâd love to see us catch up with, shoot us a reply with suggestions.
As always, if you or someone you know are working on something that could be a fit for the indieverse, weâre always on the hunt for our next investment.
Finally, from all of us to all of you, wishing you the happiest of holiday seasons.
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Thereâs a section of our website that generates more reaction than any single piece of content Iâve ever written. It says:
Weâre obsessed with the idea that someone is going to build a business doing $100M in revenue with less than 10 employees and see it as this generation of foundersâ 4 min mile. Once someone shows it can be done, many more will follow. We want to partner with the one that does to help define a repeatable playbook for those that follow.
Whether the numbers are correct or simply guide posts, itâs undeniable that how and what we build in a post-AI world is changing by the day. (Maybe hour?) This theme has been a clear focus for our investing at indie and has shown up in the form of AI infrastructure, AI services, and new work modalities enabled by AI.
This week, we sit down with a founder at the vanguard of post-AI entrepreneurship â Rahul Sonwalkar of Julius AI. One thing I was struck by in this conversation is not only the efficiency and speed that new AI tools unlock, but the ability to embed more of the humanity of the founders into the businesses they are building as both a competitive moat and differentiator. Rahul is the embodiment of this in ways that will become clear in the video.
The story of Julius begins after six pivots and countless experiments. Rahul and his team built Julius.AI by embracing a hacker mentality and following their instincts rather than conventional startup wisdom. Instead of building a massive sales organization or chasing traditional metrics, they focused on product-led growth and let users discover the value naturally. Today, Julius processes over two million lines of AI-generated code daily, helping knowledge workers analyze data without needing to code or relying on data analysts for their insights.
The funding landscape has shifted dramatically with AI-native startups. These companies can operate much more efficiently than their predecessors, giving them more optionality around fundraising. Rather than raising capital at predetermined milestones, Rahul has taken a more opportunistic approach, something we call âmacrodosing capitalâ, raising smaller amounts when offered and focusing on infrastructure investments that will pay dividends long-term.
Looking ahead, Rahul believes the key to building in the AI-era is positioning your company to benefit from, not be threatened by, improving technology. While giants like ChatGPT attempt to replicate features, Julius has found that the large playerâs marketing efforts actually educates the market and drives users to more specialized solutions. Rahul aims to go public eventually, seeing a massive opportunity in making AI-powered products accessible to everyone â not just developers.
This is a must watch for anyone curious about how AI is reshaping entrepreneurship and the opportunities it presents.
That said, if youâre looking for actionable insights or a playbook here, you may find yourself frustrated. This is an emerging field where the landscape is shifting underneath us. Any tools or tactics mentioned here could be obsolete by the time you finish watching. The core ideas of being true to your instincts, staying lean, doing more with less, and delivering value for customer feel even more timeless in the context of this conversation.
I hope you enjoy watching as much as we enjoyed making it. And if you do, please share widely. Like and subscribe. All that jazz.
And, as always, if you're working on anything in these areas that could be a fit for an investment from indie, donât hesitate to reach out.
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A few weeks back in this very email, I put out a request for a new content format we wanted to experiment with that we called âStartup Confessionalsâ.
From my note:
If you, or founders you know, are willing to share a startup confessional, weâd love to help. We can make these totally anonymized or public, whatever you're comfortable with. We'll be recording these remotely and aren't looking for hours long conversations â we're planning on editing them into quick lessons and anecdotes.
For example, here are âconfessionalâ conversations Iâve had with people one-on-one just in the last few weeks:
â Over/under raising
â Surprising/shocking fundraising stories
â Horror stories of investors/board members behaving badly
â Hiring to please investors
â Acquisitions blocked or held hostage by investors/board membersThankfully, a few heeded the call. I think this weekâs video captures the essence of what we were going for and the experiences we were hoping to mine.
This week, we have stories and lessons from some legendary founders â
Ben Kauffman
Founder of Quirky and Camp as well as CMO at Buzzfeed. Ben has an incredible knack for building brands and storytelling that has attracted some of the largest brand partnerships and most legendary investors.Harper Reed
Came into the national spotlight as the Chieff Technology Officer for Barack Obamaâs re-election campaign. Shortly after, with encouragement and funding from then-Google CEO Eric Schmidt, he founder Modest which was later acquired by PayPal. Most recently, he wound down a venture backed startup Galactic. Heâs currently exploring new ideas with his longtime collaborators.Finbarr Taylor
Got his start in tech in various staff roles at companies like Groupon, Pebble, and Y Combinator. As a co-founder of Shogun, he and his partners bootstrapped to over $1M in ARR before raising their first round of funding. That first round let to another and then another. Shogun continues to be a thriving business that Finbarr remains on the board of and actively advises in addition to angel investing. His takeaways from bootstrapping to rocketship growth to near unicorn status are lessons not to be missed or dismissed.This is our first attempt at this format and weâre so grateful to Ben, Harper, and Finbarr (as well as the others we have in the can) for being willing to wade into such uncertain waters with us.
Weâre really happy with how this turned out and welcome your feedback on how we can improve it over time.
Weâd also welcome more stories from you or your networks. If you know someone whoâd be fun/interesting/insightful on the topic of unpacking their founder, or early employee experiences and lessons, please send them our way!
As always, we hope you enjoy watching this one as much as we all enjoyed making it.
Bryce
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As someone who entered the venture industry in the wake of the Dot-com crash, I have a deep appreciation for new managers, their entry point into the industry, and how that shapes their world view. For me, it was pure carnage for the first few years of âinvestingâ. I put that in quotes because it was mostly triaging the portfolio and trying to assess which companies were worth saving and which were destined for the Dot-com dust bin.
Shortly after stepping out on my own to start OATV, another bubble burst with the Global Financial Crisisâą. My trips to NYC for board meetings were often capped off with midnight strolls through Zuccatti Park to witness the occupation of Occupy Wall Street. The markets were in free fall, checkbooks closed, and founders, once again, were at the mercy of the market.
But easy times never make for strong people and thatâs why I was excited to sit down with Turner Novak when we both found ourselves in Columbia, MO for the Main Street Summit a few weeks back. His is a âchronically onlineâ story of discovery and persistence into the world of startups and VCs. Through the use of memes, social networks, and data, Turner was able to build an audience and a âfantasy portfolioâ to land himself an internship and, eventually, a fund of his own.
Turner came into his own as an investor in the frothy times of the not-too-distant past. With wide eyes and fresh funds to deploy at his newly formed firm, Banana Capital, he set to work deploying near the peak of the ZIRP bubble. I thought it would be fun to unpack the experience of someone who built their brand online, from the midwest, and began deploying into a market thatâs rules and dynamics quickly changed on them.
With that as the goal, this one did not disappoint. A few takeaways:
- Turnerâs exposure to entrepreneurship began early with his mother running a small wedding gown business. Turner developed an interest in technology and the internet during his teenage years, teaching himself programming.
- Turnerâs path into venture capital began in college, where he joined the investment club and got hooked on investing. After working in commercial lending and for a nonprofit endowment, he started building a âfantasy VC portfolioâ on Twitter, which helped him break into the industry. His visibility on social media eventually led to his first job in venture capital.
- Turnerâs largest learning from the last few years in venture is the importance of entry points â getting in at the right valuation can make or break an investment. While many aspects of startups are unpredictable, controlling the price you pay is crucial for long-term success.
This was a really fun one and I think Turner has a bright future ahead of him as an investor and fund builder. The easy times may be over, but I can see his strength already showing through as he navigates this new reality.
I hope you enjoy listening as much as we enjoyed recording it.
PS - Today is my birthday and all I want is for you to A) subscribe to the INDIE YouTube channel (just hit that subscribe button) and B) send the next category defining company our way. Is that too much to ask?!?
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A few weeks back, I was the morning speaker at an event hosted by David Senra of FoundersPodcast (one of my favorite podcasts and people). The afternoon speaker was someone Iâd never heard of before, Shegun Otulana. The story he told resonated deeply â a Nigerian immigrant who came to study at the University of Alabama. He had the drive to be an entrepreneur and had a few early attempts that ended in a failed partnership and a pile of debt.
Feeling like he was made for more than pushing pixels at a 9-to-5, and at the urging of his wife, Shegun set out to find a problem he could solve and eventually build a business around. A chance encounter led to meeting the head of a mental health clinic in Birmingham, AL. They needed a new system to run their practice but none seemed to fit their unique needs. After failing to find them something he could help them buy, Shegun built them a simple app. That simple app led to feature requests, which led to his first paying customer and then the word of mouth began to spread.
Within 5 years, after only having raised $250,000 from local angel investors and with no experience in the industry, that side project had become a thriving business doing north of $50M in ARR and was valued at hundreds of millions of dollars. Along the way, he has able to bring in PE investors and de-risk his personal finances with several rounds of secondary. He eventually sold the business to KKR in 2021 for $1.25B, making it the largest tech exit in Alabama.
Some takeaways from this one:
â Shegun built a successful healthcare software company through disciplined, customer-obsessed growth. Their approach centered on deeply understanding customer problems at counseling centers and building the initial product based on direct feedback. They found differentiation through an innovative pricing model aligned with customer needs and an SEO forward sales motion.
â Starting with just $250,000 in initial funding, Shegun grew the business to over $50M in revenue within 5 years, eventually selling to KKR for $1.25 billion. Shegun emphasized fundamental business principles rather than chasing fundraising hype. The company maintained strong financials with 30% profit margins and 90% gross margins, growing organically without requiring additional capital on the balance sheet.
â Shegunâs leadership philosophy focused on creating a culture of transparency where team members could be vulnerable while maintaining high standards. He built a distributed team to access talent cost-effectively and gave team members significant autonomy within clear guidelines.At the conclusion of his talk at Senra's event, we both met in the hallway and gave each other a big hug. It was like finding someone who was a part of your tribe â speaking your same language and sharing your same values.
When we realized weâd both be at the Main Street Summit the following week, we decided then and there to get his story recorded. The MSS organizers were kind enough to turn over their main stage theatre for us to record in after hours and I think the resulting conversation and visuals make this one you can't skip.
I hope you enjoy listening as much as we enjoyed recording it.
As always, if you or someone you know is working on something that could be a fit for indie, don't hesitate to reach out.
Bryce
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When I reached out to Charles Broskoski, co-founder of Are.na, it was largely because I kept hearing mention of the service he'd built increasingly entering the zeitgeist among young, creative technologists.
What I thought would be a conversation about the tension between creativity in technology ended up being a much more nuanced conversation.
Some takeaways â
Arena has been operating for 13 years and has taken a slow, steady approach to growth. Arena initially struggled with fundraising but found success through a crowdfunding campaign and charging for their product. They prioritized profitability and user feedback over rapid growth or chasing trends. That trade-off leaves potential money on the table, but allows the community to flourish into its own unique place.
More Artists should start businesses â entrepreneurship provides an endless stream of problems that need solving through creativity and ingenuity. Focus on genuine passion and interest rather than chasing what seems âcoolâ or trendy with investors. Charging users early to validate the product and gain meaningful feedback.
Charles & Are.na have long been critics of traditional social media, for better and for worse. Theyâre critical of algorithmic recommendations and AI implementations that remove human discovery and idiosyncrasy from products. He believes in maintaining a human relationship with topics and interests, rather than optimizing for efficiency.
Charles and I had crossed paths several times in years past as he and the team had been working to bring Are.na to life. With each interaction, I was impressed with his vision, earnestness, and commitment to serving a community he cares deeply about.
The parts of this conversation I haven't been able to shake are the need for role models for creative technologists to follow and the trap that many fall into, chasing what's cool instead of creating something that's uniquely theirs to build.
There's something in here for everyone.
I hope you enjoy listening as much as we enjoyed recording this one.
As always, if you or someone you know is working on something that could be a fit for indie, don't hesitate to reach out.
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After wrapping this weekâs conversation with published author and ReadySetâs CEO, Y-vonne Hutchinson, I stepped out of the studio, opened my phone, and X was ablaze.
In the year of our Lord 2024, a startup had decided that an anti-woke marketing campaign was the best possible way for them to generate attention for their payroll software company. The culmination of this campaign was one of their sales affiliates posting a racist rant. The fallout from this was all over my timeline. Even the most anti-woke of the tech set found themselves embarrassed and deeply uncomfortable with the direction and velocity the pendulum was swinging.
Tech has a tortured relationship with DEI, race, and gender. The world is becoming increasingly diverse, yet the number of employees and funded startup founders from diverse backgrounds has remain unchanged, if not shrunk. Because the Me Too, George Floyd, and Black Lives Matter movements have left a bad taste in the mouths of many tech leaders, I fear weâre at risk of throwing the baby out with the bath water.
At the heart of this uncomfortable conversation is something deeply important to company cultures specifically, and the future of tech broadly, so I invited my friend Y-vonne to talk about it.
Y-vonne and her company ReadySet were part of the Indie v4 batch of companies. I have a deep respect for her, her work, and the company sheâs building. A few takeaways from this conversation:
Historical Context of DEI Efforts
Progress in diversity, equity and inclusion (DEI) often follows a pattern of advancement followed by backlash and retrenchment. This has happened repeatedly throughout U.S. history. The recent pushback against DEI initiatives can be seen as part of this historical pattern, rather than an isolated event. DEI efforts sometimes focused too much on individual change rather than systemic issues, leading to fatigue.DEI in the Tech Industry
The broad, nebulous nature of âDEIâ as a concept allowed it to become a target for criticism. Some DEI initiatives were performative rather than substantive, causing disillusionment. The tech industry initially embraced DEI efforts, but economic pressures and changing market conditions led many companies to cut DEI programs and staff. Some tech leaders have used DEI as a âboogeymanâ to justify cuts, even though the underlying issues of bias and lack of diversity remain unaddressed.DEI as a Business Imperative
Y-Vonne argues that DEI should be seen as a tool to solve real business problems like attrition, market share, and product-market fit. Companies that ignore diversity issues risk building products that donât serve increasingly diverse markets and user bases. Companies should aim for âhealthy cultureâ that enables collaboration and innovation, rather than trying to mandate diversity, but the healthiest cultures are diverse.Moving Forward
Work environments should avoid causing trauma, but shouldnât be expected to heal past traumas - thatâs not their purpose. While companies shouldnât be responsible for âhealingâ employees, leaders can adopt a more trauma-informed approach to avoid causing additional harm. Broader social and political change is needed to address systemic issues, beyond what individual companies can accomplish.The world, and its demographics, are shifting so quickly it would be a huge miss for companies not to be thinking about how their culture can reflect the broader universe or potential customers and users.
This isnât about quotas or raising or lowering bars, itâs about capturing opportunity.
This was such an engaging and energizing conversation for both Y-conne and I. We hope you enjoy listening as much as we enjoyed recording it.
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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 â
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 âlegalized casinoâ 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:
â Scheduling no meetings before noon to allow time for research and deep thinking.
â Partnering only with people who share similar values.
â Balancing effort and recovery to avoid burnout.
â Being more upfront and decisive with entrepreneurs, trusting his intuition.As a coach, Steve helps clients navigate major life/career transitions and âego deathsâ 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 â
"Maybe itâs just me.
But I keep running into the same conversations around career crisis, purpose, and transitions. Several times a week, Iâll meet up for lunch, sink into a DM, or sift through a Telegram chat, and a friend will confide that theyâre experiencing a tough time. When I comfort them, they are surprised that theyâre not the only ones struggling with finances, that other industries arenât 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.
â 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.
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In April 2015, I read an article that elicited a reaction Iâd 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 Instagramâs 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 âRoommatesâ 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. Thatâs 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 â
1) Speak to yourself and your own interests.
2) Listen to your audience.
3) Truly know your audience.Recording this conversation in Angieâs 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. Thereâs no doubt in my mind that thereâs much more runway ahead for her and TSR. Hopefully that can all happen without landing me in any more diss tracksâŠ
We hope you enjoy listening as much as we enjoyed recording this one.
And as always, if youâre working on something that could be a fit for indie, or know someone who is, donât hesitate to reach out.B
â Bryce
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