MMy First Million
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MFM Demo Day09 June 2022

MFM Demo Day: 5 Startups Pitch Sam & Shaan and Raise $1.7M

5Frameworks
9Insights

Frameworks in this episode

Influence7 steps

The Guess-The-Number Opening

Open by asking your audience to guess your headline market number, because being wrong makes them remember it.

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Communication6 steps

The Play-It-Back Clarity Test

Say the first 60 seconds of your pitch to someone, then make them explain your company back to you.

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Strategy6 steps

The Public Math Question

Ask a founder to walk you to $100M in revenue out loud — you are testing whether they have ever done the arithmetic, not whether the number is right.

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Communication6 steps

The X-Y-Z Story Pitch

Replace the abstract description of your category with one named company, one specific problem, and what they tried before you.

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Finance6 steps

Traction Hygiene: Say the Number You Actually Keep

Never say ARR when you mean run rate, never say revenue when you mean GMV — state net revenue first, then everything else.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Takeaway· 2

Takeaway46:00

What the Hosts Are Actually Judging

Between pitches the hosts articulate their real evaluation criteria, which turn out to have little to do with the deck. Shaan wants to help a rocket already in motion rather than push something at a standstill. Sam warns that charisma is a two-way signal — his best and worst investments both came from charismatic CEOs. Both note the structural disadvantage non-native English speakers face, and Shaan explains that the 'how do you get to $100M' question is really a test of whether the founder has ever done the math before.

  • Shaan: needing the investor to supply the strategy is usually a bad sign for the investment.
  • Sam: best and worst investments both traced to charismatic CEOs — charm cuts both ways.
  • Non-native English speakers are at a real structural disadvantage; the hosts argue the deck and story must carry more of the load as a universal language.
  • The $100M question tests whether the math is recalled or invented on the spot.
  • Founders should give downside protection (a concrete worst-case multiple) and an honest ceiling, not an evasive 'we're not thinking about an exit'.
  • Calibration: downside answers land on angels investing their own money; institutional VCs need the energy on the upside.
  • Co-founder pitching hygiene: agree in advance who fields technical versus growth questions, so deferral looks deliberate.

“i want to be helping a rocket that's already going and not like pushing something that's at a standstill”

Shaan Puri · 1:21:00

“we don't do public math but we sure as hell make founders do public math when they pitch us”

Shaan Puri · 1:05:30
#angel-investing#founder-assessment#pitching#due-diligence
Takeaway1:25:00

The Rankings, and Pitching Stonks for House Money

The hosts rank all five companies. Sam puts Nickelpass and the group-airfare business at the top, 5X in the middle, and Munch and the pool roll-up at the bottom. Shaan ranks group airfare first, the pool roll-up second on business quality but flags he wouldn't invest in the founder because they 'speak different languages', and Nickelpass third. They then pitch the Stonks founder on giving them house money to invest live — modelled explicitly on how the crypto gambling site Stake fronts Drake money to gamble on stream.

  • Sam's ranking: Nickelpass and group airfare top, 5X middle, Munch and pool roll-up bottom.
  • Shaan's ranking: group airfare first, pool roll-up strong on business but weak on founder fit, Nickelpass third.
  • Shaan on the pool founder: 'he speaks like digging holes in the ground and building pools and I speak like frameworks.'
  • The house-money pitch: Stake reportedly gives Drake ~$10-20M/month to gamble on stream to attract users.
  • Stonks counter-offered one check into each host's favourite startup per event; the hosts pushed for carry instead.
  • The Stonks founder and Shaan were former competitors — Streamlabs versus Bebo, both building tools for Twitch streamers.
  • Running gag: the 'bookshelf meme', mock-rejecting founders for not displaying Zero to One or The Lean Startup.

“you don't seem like you do yoga i'm out you're on a gamer chair you're not like on a treadmill desk i'm out you eat…”

Sam Parr · 1:24:30
#angel-investing#creator-economy#deal-structure#rankings

context· 1

context00:00

The Format: Five Startups, Two Minutes Each, a Thousand People Watching

Sam and Shaan run a live demo day on Stonks.com — Sam discloses he is an investor, Shaan is not. Five startups get roughly two minutes to pitch and eight minutes of questioning, with a live chat of over a thousand people scoring pitches and heckling in real time. Neither host has seen the companies in advance. The chat turns out to be a genuine participant: it supplies domain-name suggestions, clarity scores, and running commentary.

  • Five startups, ~2 minutes to pitch, ~8 minutes of Q&A each.
  • Sam is a Stonks investor; Shaan is not — disclosed up front.
  • Over a thousand people watching live with an active chat.
  • Hosts saw nothing about the companies beforehand.
  • Attendees could signal investment interest in-platform; one founder ended with $75,000 of interest.
  • The platform crashed repeatedly mid-event during a code migration.

“five startups are going to pitch us and we're gonna maybe invest but very likely tear them apart and also complement them”

Sam Parr · 00:30
#demo-day#live-events#angel-investing#format

teardown· 5

teardown02:00

5X: Great Traction, Incomprehensible Pitch

Darris, first data engineer at Salesforce and formerly running data for WeWork, pitches 5X — an end-to-end data platform that licenses and integrates the vendors in the modern data stack, plus pre-trained engineers as a service. Both hosts spend most of the slot simply trying to understand what it does. The business underneath is strong: ~$1M run rate in under a year, zero marketing, roughly 10-15 customers at ~$10K/month, profitable by month end.

  • Founder was first data engineer at Salesforce, later led data at WeWork.
  • ~$1M run rate in under a year with zero marketing, all word of mouth.
  • ~10-15 customers at ~$10K/month average order value.
  • Raising $300K at a $25M valuation; expects profitability that month.
  • Chicken-and-egg problem: needs customers to convince vendors to grant API access, and vendors to serve customers.
  • Shaan's critique included the pitch being delivered from a distractingly nice house in Bali — 'I kind of like my founders to be a little more scrappy.'
  • Open question both hosts flagged: how much of this is software versus a consulting business.

“a good pitch is not necessarily a good business but good traction is usually a good business and so you actually have good traction at…”

Shaan Puri · 12:30
#data-infrastructure#b2b-saas#pitch-feedback#traction
teardown15:30

Group Airfare: A $130B Market Still Booked by Phone

Kenny pitches a B2B Expedia for group airfare — flights of 10 or more people, a category that before them was transacted entirely over the phone across five distinct stages. Group travel is ~$130 billion of annual spend, roughly 5% of airline revenue and ~225 million passengers. Both hosts rated it the clearest pitch of the day, and Sam ranked it his number one.

  • Group airfare = flights of 10+; ~$130B annual spend, ~5% of airline revenue, ~225M passengers pre-pandemic.
  • Launched flight shopping October 2021; the company started in 2018 as a trip-management tool and barely survived the pandemic.
  • $4.2M gross bookings January-April at a 10-15% margin; ~$150K/month actual revenue; ~$1,700 revenue per group; 40 corporate customers; 11 staff.
  • Acquisition: a referral program paying ~$5 per ticket booked, plus old-school industry events; SEO barely tapped at ~72 cents a click pre-pandemic.
  • Built on the Saber and Amadeus GDS systems with custom tooling for group limitations.
  • Raising $1.5M at a $15M cap — derived by taking projected ~$1.5M annual revenue times 10.
  • Corporate offsites emerged as the fastest-growing segment post-pandemic.

“in 2022 this is insane that a world with so much money in it operates totally offline”

Kenny (Bukhari) · 16:30

“there's a really clear path for us that we get to like 50 million dollars in revenue in the next like five to six years…”

Kenny (Bukhari) · 26:30
#marketplace#travel-tech#b2b#pitch-feedback
teardown30:30

Munch: AI Content Repurposing, and the Jellysmack Question

Oren pitches Munch — AI that analyses a long-form video and automatically cuts the three-to-five most engaging segments into vertical clips for TikTok, Reels and Shorts, with ambitions to become the central platform for creators. Shaan rates the slide pitch as putting him to sleep but the live demo as the most impressive part, and passes on the investment. The hosts press hard on whether the technology becomes a commodity.

  • Analyses scenes, visuals, audio effects and transcribed speech to pick clips, then reformats landscape to portrait.
  • Content creation market cited at ~$65B growing 15% annually, toward ~$140B by 2026.
  • Raising $500K on top of $900K already raised; $250K committed.
  • Jellysmack comparison: 6.5 years, ~500 customers, ~2,000 employees doing it manually — Munch's claim is full automation and self-service.
  • Shaan's commodity concern: Buffer's scheduling became table stakes; Jellysmack may really monetise via ad revenue splits, not the tech.
  • Traction: ~2,000 users in under two months via preemptively-made videos emailed to a database of ~800,000 YouTube creators at a 4-5% conversion, plus influencer marketing.
  • Shaan passed — creators are hard to reach through the noise, and 'anytime somebody's using AI I'm like, I gotta see it to believe it.'

“your pitch with the slides was putting me to sleep but the pitch where you showed my face i'm like oh wait this is me…”

Shaan Puri · 41:30
#creator-economy#ai#content-repurposing#pitch-feedback
teardown47:30

Nickelpass: Enterprise Bundled News, and a Broken Cap Table

Zaza (ex-Huffington Post international expansion) and Allison (ex-banker) pitch Nickelpass — a Chrome extension that removes paywalls for employees because their employer bought a bundled multi-publisher licence at up to 70% off retail. Both hosts liked the product and the pitch; Shaan was blunt that the cap table looked bad after raising ~$5M and now raising at a $15M valuation, following a pivot away from blockchain micropayments.

  • Network of 200+ publications including LA Times, Time, Crunchbase Pro — and niche trades like Beer Business Daily for Anheuser-Busch.
  • 125-150 corporate customers covering 400,000+ employees; customers include Anheuser-Busch, Visa, Publicis and Havas.
  • $1.2M ARR, tracking to $3M gross by year end (~$1.5M net); gross margin 44-55%; base package ~$23.95/user/month.
  • Average customer contract has grown from $7-10K/year to ~$50K.
  • Publishers convert under 1% of visitors to subscriptions, making bulk licensing a win-win.
  • Path to $100M: ~10,000 companies, via raising in-account penetration from 1% to 3% and sector penetration from 0.01% toward 1%.
  • Pivoted from blockchain micropayments — Shaan called that 'respect for pivoting away from blockchain, that shows me you're a clear and independent thinker.'
  • Raised ~$5M previously; Shaan: 'your product is awesome, it sounds like your cap table is shitty, to be blunt.'

“news used to cost a nickel”

Allison (Nickelpass) · 1:03:00

“i think your product is awesome it sounds like your cap table is shitty to be blunt”

Shaan Puri · 1:02:30
#b2b-saas#media#cap-table#pitch-feedback
teardown1:09:30

Little Duckies: Rolling Up Retiring Pool Companies

Colton pitches a roll-up of South Florida pool construction companies bought from retiring owners. He built his own pool maintenance business to ~$18K MRR in under three years and funded the first two acquisitions by selling his and his father-in-law's houses. The hosts think the business is strong and the pitch is confused — Shaan reconstructs it live as a private-equity roll-up story rather than a pool company.

  • Own maintenance business at ~$18K monthly recurring revenue in under three years.
  • First acquisition negotiated at roughly a multiple of four months of monthly gross revenue.
  • Two purchase contracts signed, one in negotiation; projecting $10.3M gross for 2023 with 13% yearly increase.
  • Structure: buy the company and the crew, retain the owner as a two-year consultant training a new project manager, inherit the two-year booked contract backlog.
  • Moat is licensing: four years of experience plus board approval to get a license, so millennials and Gen Z cannot simply enter.
  • Financing detail he buried: ~10% down with seller financing over five years and a balloon payment — Shaan: 'dude, why didn't you say that?'
  • Operational edge: bringing subcontractors in-house, 3D pool modelling emailed to customers, digital permitting via video call — at least 20% faster builds.

“i buy successful profitable companies and i'm just a better operator than the mom and pop and i'm gonna aggregate these because i just have…”

Shaan Puri · 1:23:30
#roll-up#private-equity#acquisition#seller-financing

insight· 1

insight1:15:30

The Baby-Boomer Buyout Thesis

Prompted by the pool roll-up, both hosts surface the thesis behind one of their best investments: buying businesses from baby boomers who want to retire and whose children don't want to take over. They cite their friend Sieva's Enduring Ventures (which bought Dolphin Pools in Arizona), and Sam Zell — the man who effectively created the REIT — saying he is now making more money buying businesses from retiring boomers than he ever made in real estate.

  • Both hosts invested in Enduring Ventures, founded on exactly this thesis — one of their best investments.
  • Enduring Ventures bought Dolphin Pools in Arizona and, per Shaan, they're 'killing it'.
  • Sam Zell — creator of the REIT, former owner of Schwinn, the Tribune and Waste Management — says boomer buyouts now beat his real estate returns.
  • The two viable routes: buy cheap and install a manager (Sieva's model), or add technology to a trade and scale it.
  • The tech-enabled variant: the Upwork founder's new fence installation company, Ergeon, bootstrapped to ~400 employees before raising ~$40M.
  • Shaan's warning to the founder: pick one route and go all in — his website being on Wix signalled tech wasn't where he'd win.

“he is making more money off of buying businesses from baby boomers who don't want to pass their companies onto the kids than he has…”

Sam Parr · 1:16:00
#acquisition-entrepreneurship#roll-up#investing-thesis#small-business