Podcast Summary: Our Future Podcast #47

Episode Title: How We Sold Our Bootstrapped Startup In 2 Years
Date: June 19, 2024
Hosts: Michael Sikand (“C”) and Simran Sandhu (“B”)
Theme: Lessons, mindsets, and tactics from building and selling a bootstrapped media startup to Morning Brew—what worked, what didn’t, and what young founders need to know.

Episode Overview

This special episode flips the script: instead of interviewing ambitious young founders, hosts Michael and Simran share their firsthand story—how they built their media company “Our Future” from humble college beginnings, navigated the pandemic, and landed an acquisition by Morning Brew all in under two years. They dive deep into the “scrappy” tactics, pivotal lessons, and mindset shifts that defined their journey, aiming to offer actionable advice for aspiring and early-stage entrepreneurs.

Key Discussion Points and Insights

1. Origins and Early Days

• Not the First Idea: Their original concept was a D2C beverage company called “Jet Coffee”—a plan that never materialized but still excites them (“Someone should definitely go run with it!” [02:55]).
• Why Media & Podcasting: With minimal capital as college students, podcasting emerged as their 'cheat code'—a low-barrier way to network and build leverage with industry leaders, particularly during Covid when everyone was online ([04:15]).

“Podcasts were the easiest way to... talk and network with really important people and get our names out there. It’s Covid, so why the hell not?”
— Simran, [04:15]

• Building Connections: Interviewing executives as 19–20-year-olds gave them credibility, open doors to internships, and the confidence that providing a platform is valuable—even if you’re young ([06:12]).

2. How to Do Podcasting (and Networking) Right

• Do It Differently: The hosts note that while many young people start podcasts, few execute them with intentional branding, strong distribution, and passion. Most don’t “put their heart and soul into it” ([06:12]).
• Key Tactic: Use clever, ambitious subject lines (“#1 show for Gen Z”), aggregate follower numbers across channels to accelerate credibility, and always “pitch bigger than reality” in early days ([07:05]).

“It’s really just about the tact and the strategy you bring to it... I still think there’s tremendous opportunity... even if it doesn't become a business, it’s going to open a ton of doors for you.”
— Michael, [07:05]

3. Forming Partnerships and Teaming Up

• Finding a Co-founder: Michael and Simran became business partners after nearly two years of friendship built on organic connection, not transactionality ([10:15]).
  • Advice: Build relationships with people interested in your industry; you don't have to join forces immediately—trust and understanding develop over time.
• Complimentary Skillsets: They attribute success to distinct personalities: Michael was the outgoing “delusional” pitchman; Simran, the logical and pragmatic counterpart ([00:58], [24:00]).

“Having very different personalities... actually helped us with investor conversations and acquisition conversations.”
— Simran, [24:00]

4. Business Model Evolution & Pivoting

• Short-form Video as the Differentiator:
  • Inspired by TikTok trends outside the business realm, they applied similar styles to business content, finding a high-engagement format no one else was using in their niche ([13:34]).
  • “At the end of the day... find an existing model that works rather than trying to recreate the wheel.” — Simran, [13:34]
• From Pure Media to Services:
  • As the ad-based media model hit limits—slow ad cycles, unstable revenues—they switched to agency-style short form video production for B2B SaaS clients, starting with a viral win on My First Million → landing HubSpot ([19:00]).
  • This hybrid “media disguised as an agency” unlocked recurring, stable revenue, making them attractive for acquisition ([21:34]).

“Advertising isn’t a meritocracy... repeatable, recurring revenue is what enabled our business to stand on its own.”
— Michael, [21:34]

5. Selling the Company: The Morning Brew Deal

• Positioning & FOMO:
  • Always positioned themselves as “the next big thing,” using exclusivity (“we’re only taking three big advertisers this quarter”) to manufacture demand—even if the reality was scrappier ([15:26]).
  • Simran shares their go-to closing line in fundraising:

    “I got one spot left in this round. Let me know if you’re in.”
    — Simran, [15:26]

• Negotiation Lessons:
  • Maintain confidence/delusion—never let an acquirer think you’re desperate ([25:59]).
  • Acquisition talks can “pollute your mind”—don’t count on a deal closing until it actually does; keep focusing on growth ([25:59]).
• Decision Maker Principle:
  • Get to the actual decision maker early. Deals often stall because you’re talking to a middleman who can’t close ([28:20]).

    “If the decision maker doesn’t follow up... they probably don’t want to do the deal.”
    — Michael, [28:26]

• Non-Negotiables & Clarity:
  • Figure out the very few critical deal points (not the laundry list). Negotiate those early—otherwise, you risk wasting time ([29:08]).
  • They secured their own show with Morning Brew as an acquisition “cherry on top”—a non-negotiable for their personal & brand growth ([31:50]).

6. Mindset & Meta-Lessons for Founders

• Act Like You Have No Competition:
  • “Pitch yourself like competition doesn’t exist... believe you’re the only one, and bring that energy, confidence to other people.” — Michael, [35:10]
• Define Your Own Rules:
  • Unique positioning = freedom to set your prices and narrative.

    “We just kept raising our prices until we heard ‘no’... that’s the value in unique positioning.”
    — Simran, [35:42]

• Beware of Advice Overload:
  • Most advice is agenda-driven: VCs want you to raise, bootstrappers want you to bootstrap, etc.

    “Everybody’s playing their own agenda... you want to set your own navigation address.”
    — Michael, [37:45]

• Find Your Wave, Not Just a Playbook:
  • Reference successful businesses, but look for the new, unsaturated “arena” that fits your moment.

    “If we had tried to build the Morning Brew [in 2022], we wouldn’t have been able to.”
    — Michael, [40:12]

Notable Quotes & Memorable Moments

• “You were the more bold one out of the two of us... and I was the more calm, logical, pragmatic.”
  — Simran, [00:58] and [24:00]
• “When you’re young and you don’t have any status or credibility, you need to be somewhat delusional... and pitch yourself in a really big way.”
  — Michael, [13:00]
• “The value of being early... at the time, no one was thinking about services in this way.”
  — Simran, [22:34]
• “Deals don’t go through. Most deals fall through... it can pollute your mind, so keep focusing on building your business and do your thing.”
  — Michael, [25:59]
• “The advice you get will always reflect what worked for them... but the business environment now is very different.”
  — Simran, [39:00]

Timestamps for Key Segments

| Timestamp | Segment/Topic | |-------------|-------------------------------------------------------------------| | 02:39 | Jet Coffee origins, early ambitions | | 04:15 | Starting a podcast as a networking ‘cheat code’ | | 06:12 | The right way to do a youth-led podcast | | 10:15 | Co-founding via friendship, not transactionality | | 13:34 | Borrowing working models, TikTok inspiration | | 17:16 | Using FOMO tactics for deals and fundraising | | 17:45-19:00 | From advertising to services business with B2B clients | | 21:34 | Advantages of recurring revenue, hybrid model | | 24:00 | Good cop/bad cop—how their personalities worked in negotiations | | 25:59 | Lessons from the Morning Brew acquisition process | | 28:20 | Importance of talking to decision makers in deals | | 29:08 | Structuring deal negotiations—focus on the few, real priorities | | 31:50 | Winning the right to keep their podcast as a non-negotiable | | 35:10 | Ignore competitors, build your own confidence | | 37:45 | Be wary of advice—stick to your vision | | 40:12 | Find your own wave, reference but don’t copy successful models |

Flow & Tone

The conversation is consistently energetic, forthright, and infused with the unfakeable optimism and resourcefulness of scrappy young founders. There’s lots of good-natured ribbing, encouragement for future founders, and tactical honesty about the real challenges and mind games of entrepreneurship. Both hosts share hard-won wisdom without sugarcoating the lows or overhyping the highs.

Final Takeaways & Advice for Young Entrepreneurs

• Leverage what you can control—network, energy, and willingness to learn
• Take inspiration, but don’t blindly copy.
• Be confident, even delusional, in your ambition and pitch.
• Don’t count on acquisition or outside capital—keep building as if it won’t come.
• Ignore most competitors—craft your own narrative and pricing.
• Always analyze whose advice you’re following and their real incentives.
• Secure your non-negotiables in writing if you do exit.

For questions, topic suggestions, or just to connect, reach out to Michael and Simran (links in the show notes). They’re eager to help the next wave of Gen Z builders.