Jun 23, 2022 · 1h 6m · startup-ideas
How to Build a Brand of the Future
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Midday Squares co-founder Nick Saltarelli joins hosts Sahil Bloom and Greg Isenberg to break down how radical authenticity, vertical in-house manufacturing, and a media-first brand strategy can build a generational consumer enterprise.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 8% of the talking time here. How this is scored →
Greg as informed peer 3.9 Guest teaching 4.6 Guest disagreement 2.4 Greg pushing back 1.3
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 45:40 Nick rejects board hesitation
Nick fiercely dismisses his board of directors' demand for slow test marketing, mocking the idea of acting like L'Oreal when operating in the trenches of a fast-moving startup.
Hardest push from Greg ▶ 33:23 Greg challenges hard-concept framing with authenticityGreg interjects to correct Nick's framework by insisting that tackling hard problems alone is insufficient without genuine personal authenticity.
Biggest teaching moment ▶ 13:48 Nick debunks DTC marginsNick immediately corrects the hosts' premise that Midday Squares is a direct-to-consumer play, detailing the mathematical and logistical realities of wholesale distribution.
Greg holds their own ▶ 41:40 Greg grounds startup odds vs corporate techGreg demonstrates insider realism by arguing that founders chasing money are statistically foolish compared to corporate tech employees, reframing the true motive for founding startups.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Introductions, Banter, and the 'Bring the Heat' Mindset | 4 | 1 | 1 | 1 | Greg and Sahil kick off the episode with playful banter about hairstyles before introducing Nick's bold brand positioning. The tone is highly collaborative and warm, with no adversarial dynamic. | |
| Sponsor Break: Private Real Estate Portfolio Diversification with Fundrise | 0 | 0 | 0 | 0 | Mid-roll sponsor reads for Fundrise and Element delivered by Sahil Bloom. As a scripted sponsor read monologue, all interaction metrics are zero. | |
| The Montreal Entrepreneurship Mafia and Big Fish Mindsets | 6 | 4 | 2 | 2 | Greg and Nick bond over their shared Montreal upbringing and mentor Rory Olson, trading stories about wealth concentration and entrepreneurial ecosystems. Sahil brings in conceptual frameworks like the tyranny of the OR versus the genius of the AND. | |
| Debunking Pure DTC: Wholesale Value and Manufacturing Realities | 3 | 8 | 5 | 1 | Nick immediately interrupts and corrects the hosts' assumption that Midday Squares is a direct-to-consumer brand, educating them on why pure DTC unit economics fail compared to wholesale retail. Sahil readily concedes and asks for elaboration on changing customer acquisition costs. | |
| Building a Brand Like a Band: The Media-First Playbook | 5 | 7 | 2 | 2 | Greg queries how Midday Squares incorporates ideas from other CPG brands, prompting Nick to outline his strategy of running a CPG brand like a rock band and media company. Greg adds helpful context on Figs while Nick details the power of reality-show-style storytelling. | |
| Vertical Manufacturing Moats and Contrarian Market Selection | 4 | 8 | 4 | 1 | Nick breaks down the counter-intuitive necessity of vertical manufacturing in saturated markets and mocks the asset-light co-packer model by comparing it to outsourcing a tech company's core software engineering. The hosts listen attentively, validating his perspective. | |
| Exploiting Structural Blindspots and Doubling Down on Hard Truths | 5 | 6 | 3 | 3 | Sahil and Nick discuss contrarian decision-making and structural moats created by capital-intensive plants. Greg interjects to push for the missing ingredient of authenticity, citing co-founder Jake's viral videos, which Nick readily embraces. | |
| Sponsor Break: Element Electrolyte Supplementation | 0 | 0 | 0 | 0 | Mid-roll commercial segment promoting Element electrolytes and Fundrise real estate investing. No interview dialogue takes place. | |
| The Boring-Complex Matrix and the 30-Year Entrepreneurial Horizon | 5 | 5 | 2 | 2 | Sahil introduces Charlie Songhurst's complex-versus-boring matrix, leading Nick to discuss his shift away from purely pursuing money toward building a multi-decade legacy brand. Greg reinforces the argument by emphasizing the harsh realities of startup survival rates. | |
| Mindset vs Experience and Standing Firm Against Board Pushback | 4 | 7 | 6 | 2 | Nick dismisses the standard reverence for industry experience, calling older advisors destructive when they enforce outdated playbooks, and shares how he rejected his board's request for test marketing. Greg probes whether defying the board was difficult, allowing Nick to emphasize founder conviction. | |
| Betting the Farm on Single Squares and Retaining Voting Control | 5 | 6 | 4 | 1 | Nick describes the risky decision to transition from two squares to one square despite short-term financial headwinds and reveals his tactic of slashing valuations to preserve absolute voting control. Greg and Sahil support his thesis on long-term founder stewardship. | |
| Radical Candor, Personal Tragedy, and First-Principles Living | 4 | 4 | 2 | 1 | Greg praises Nick's transparent and unfiltered communication style, which prompts Nick to reflect on how processing his father's death at age ten instilled fierce first-principles independence. The tone is deeply personal and respectful. | |
| The Apprenticeship Hack and Jeff Bezos's Invariance Framework | 5 | 5 | 1 | 1 | Sahil poses a hypothetical reboot scenario, prompting Nick to share his playbook of acting as an indispensable steward and apprentice to established leaders. Sahil connects this to Jeff Bezos's invariance mental model, which Nick illustrates through the timeless appeal of chocolate. | |
| Startup Turmoil, Factory Scale, and Sleep as an Emotional Buffer | 4 | 3 | 1 | 1 | Greg inquires about Nick's sleep schedule amid existential operational pressure, leading Nick to discuss personal sacrifices, plant milestones, and mental health management before the hosts wrap up the show with enthusiastic praise. |
Statements from this episode (27)
Nick Saltarelli: Mentor Rory Olson achieved over three nine-figure business exits
“Rory's just a really predominant entrepreneur out of Montreal. Has done Over three, nine figure exits over three took a cut and was the founder of Paysafe, which I think is today still the largest, third largest e-wallet in the world, if I'm not mistaken.”
Nick Saltarelli: Mid-Day Squares chose Montreal to bring Nike-like energy to the city
“One of the main reasons why we chose to build midday squares here, we were looking at Toronto and LA is just, I always, I have this, you know, vision of bringing the energy that Nike brought to Oregon to Montreal.”
Nick Saltarelli: Montreal's Desmarais family owns one-third of Adidas
“The Demare family, which is from Montreal owns one third of Adidas, right? That means they own one third of the easiest deal. They own, you know, they own some serious stuff and that's a Montreal family.”
Nick Saltarelli: Whether to fundraise is simple—raise if you lack capital, otherwise don't
“I think people overanalyze a lot of things like all the way down to should you fundraise? Should you not fundraise? It just doesn't fucking matter. All that matters is that you have a goal in mind and you have to get there and to get there is going to have, yo…”
Saltarelli: Pure DTC costs more to scale than traditional retail distribution
“What I think people forgot was how trained humans are in that buying cycle and how much more money it actually costed to scale than to actually just play within the distribution channels that exist.”
Saltarelli: Retail wholesale revenue is as reliable as software recurring revenue
“Retail wholesale revenue is as good as software. It is like clockwork every 20 days. If you have a product that repurchases, meaning that that's the good sign, right? If people are coming back into their grocery habits or any of those, like it's like clockwork…”
Saltarelli: Midday Squares is a manufacturing business, not DTC
“DTC is just a component of what we are, but we are absolutely not a DTC business. So we are manufacturing business that, that runs a brand.”
Saltarelli: Midday Squares is a media company funded by chocolate
“Yes, we're a manufacturer yes, we're a CPG product, but to really understand what we're doing from a marketing perspective is we're a media company and our Patreon is our chocolate.”
Saltarelli: Great products can celebritize founders instead of relying on celebrities
“You can actually use the product if great to celebritize yourself and then bring out an audience that's really committed to seeing your growth.”
Saltarelli: SKIMS rivaled Spanx rapidly because storytelling drives consumer purchasing
“SKIMS was able to come and really come after Sarah Blakely's Spanx in a very, very fast period of time. And I think that's really because it's driven from a narrative. People like to buy into stories and then the stories lead to the product.”
Saltarelli: Saturated Markets Require In-House Production for Real Innovation
“The problem with saturation is that by definition, saturation is an uninnovated market. And to bring true innovation to market, you almost are never going to be able to show up to a co manufacturer and have that happen regardless of what you're building.”
Saltarelli: Midday Squares Met With 26 Co-Manufacturers Before In-House Pivot
“So for us, we went to go see 26 different co manufacturers.”
Saltarelli: A Founder Cannot Build the Next Nike Using Contract Manufacturers
“You might be able to build a company in five years and flip it to Kellogg's or you know, Nestle, but you ain't building the next Nike with Comends.”
Saltarelli: Big CPG won't reproduce manufacturing lines under $300M revenue
“They won't even look at reproducing a manufacturing line internally unless they have proof points of three hundred million dollars a year of revenue.”
Saltarelli: Tackling hard problems makes fundraising and recruiting easier
“It's attracting talents easier when you're going after really hard things. Raising money is easier when you're going after really hard things. It just makes everything so much easier.”
Saltarelli: Building a brand is the least probabilistic path to wealth
“If you're trying to become a millionaire, building a brand is not the fastest way to do it. If anything, it's actually the least probabilistic way to do it.”
Saltarelli: Mid-Day Squares operates on a 25-to-35-year time horizon
“We're doing this for 2535 years. Again, everybody I meet is trying to build businesses for five years and flipping it.”
Saltarelli: Manufacturing plant returns fail under a five-year horizon
“Do you think that we would have ever built a manufacturing plant if we had a five-year business plan? Absolutely not. You could not make the returns work.”
Saltarelli: Experienced veterans often do more damage than good to founders
“Like when it comes to experienced people, they actually do more damage in their square-ness. Even like myself, I will be that person when I'm 70, going back to a 20 year old, I will be more destructive than I am positive to that person because I will have crea…”
Saltarelli: Mid-Day Squares switched from two squares to one at $2.49
“We were going through, we just transitioned the whole business from a two square business to a one square business. We needed to make these decision quicks. Costs were rising. We wanted to do a price increase. We had data from the customer that they wanted to …”
Saltarelli: Founders are the scarce asset, not capital or board members
“Founders need to start taking back not control, but conviction that we are the people that are on the front lines doing the stuff. We are the scarce ones. Money's of abundance. Investors are of abundance. Boards are of abundance.”
Saltarelli: Midday Squares outsold Perfect Bar to become #1 in US
“We beat perfect bar in the last 24 weeks as the number one bar in the U S.”
Nick Saltarelli: Midday Squares accepts $50M valuation cuts for absolute board control
“We fundraise at lower valuations every single round to control the board and have a complete voting control. So we've taken 10, fifty million dollar cuts from the valuation in order to have those provisions in the term sheets.”
Saltarelli: None of the top 10 public CPG companies are founder-led
“In CPG, there's not one founder led top 10 company in the publicly traded ranks.”
Saltarelli: Serving as someone's right hand is the best career launchpad
“And go become the right hand person to the right person, because that is a launch pad that, like, I mean, putting yourself secondary to someone is always the best way.”