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My First Million

How two straight guys bought Grindr and made $2B

Published October 13, 2025
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About This Episode

The hosts interview two entrepreneurs and operators who led the acquisition of Grindr from its Chinese owner under a forced divestiture and then took it public for a $2 billion valuation. They explain Grindr's origin, why U.S. regulators forced the sale, how homophobia and perceived risks created a buyer's opportunity, and the operational turnaround they executed across talent, tech, product, trust and safety, and monetization. The conversation broadens into how they approach private equity deals vs. startups, the use of leverage and risk reduction, opportunities and disruption in AI, crypto, and healthcare, and reflections on long careers in tech, investing, and choosing the right partners.

Topics Covered

Entrepreneurship Private equity Business growth and scaling Data privacy and surveillance Online safety Venture capital Investing Artificial intelligence Crypto Healthcare system

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Grindr was originally founded by Joel Simkai, later sold to a Chinese company, and then forced by U.S. regulators (CFIUS) to be divested due to national-security and blackmail concerns around user data.
  • Homophobia among institutional investors and multiple perceived problems around privacy, PR, and Chinese ownership depressed the sale competition and price, creating an opening for nontraditional buyers.
  • The buyers paid around $600 million for a business doing roughly $100 million in revenue and $45 million in EBITDA, then took it public for $2 billion in about two and a half years, creating roughly a 9x return on $200 million of equity.
  • Their turnaround plan centered on replacing much of the talent (especially engineering), rebuilding the tech stack, tightening privacy and safety, then applying a proven dating-app monetization playbook to upgrade product and pricing.
  • They emphasize that private equity is as much about risk reduction and deal structuring (equity, debt, earn-outs) as it is about upside, and that leverage can dramatically improve returns if cash flows are stable.
  • For experienced operators, buying and improving existing profitable businesses can be a more controllable and less binary path than venture-backed startups, which often have long, uncertain timelines and product‑market‑fit risk.
  • They see AI, crypto, and parts of healthcare, legal, and engineering as ripe for disruption because these areas have rich documentation, high spend, and often frustrated customers.
  • One guest co-founded an AI "middleware" venture called Agency to connect web 2.0 commerce sites with agentic AI systems, acting as a glue layer between traditional websites and AI agents.
  • They argue that long-term entrepreneurial success often comes from multiple attempts over decades, emotional leveling (not overreacting to highs or lows), and partnering with people you deeply trust and enjoy working with.
  • Stories about early interactions with founders like Travis Kalanick, Jack Dorsey, Brian Chesky, and Naval Ravikant illustrate that early genius is not always obvious and that luck and timing significantly shape outcomes.

Podcast Notes

Introduction and setup of the Grindr story

Hosts explain why they wanted these guests on

Hosts discovered an amazing story behind Grindr and realized these two guests were the ones who bought it, took it public, and made it a home run[0:33]
They note the guests have generally stayed behind the scenes and rarely talked publicly about their work[0:45]
The hosts frame the episode as a chance for "story time" about how the guests ended up owning Grindr, what it was before them, and what happened after[1:10]

Background on Grindr and the forced sale

Founding of Grindr and original sale to Chinese owner

Grindr was created about 15 years ago by Joel Simkai, a gay man who wanted a GPS-enabled app to find other gay men nearby[1:20]
• The guests compare the GPS-based concept to Uber emerging once smartphones and location became ubiquitous
Grindr took off and Joel eventually sold it to a Chinese company called Kunlin[1:46]
Joel owned about 90% of the company at exit and sold it for roughly $260 million, so he did very well[2:21]

CFIUS intervention and national security concerns

CFIUS (Committee for Foreign Investment in the U.S.) later forced a sale of Grindr from Chinese ownership to U.S. owners[1:53]
• The concern was that data collected by Grindr could be misused by the Chinese government, including for blackmail or surveillance of sensitive individuals
One guest explains how knowing specific users (e.g., in the White House) and tracking their movements could reveal sensitive information, like when the president is about to leave[3:06]
• They mention reports of soldiers on both sides of the Ukraine war using Grindr, Olympians being outed in the Olympic village, and Grindr implementing work to avoid extreme abuse cases
They emphasize that hypothetically, if Chinese authorities had server access and intent, they could identify closeted users in politics, military, or high positions and potentially blackmail them[3:38]

Mechanics of the forced sale

CFIUS gives the company one year to sell to a U.S. ownership group or else the government will take control of the business[4:01]
• During that year, a CFIUS group composed partly of intelligence officials and elected administrators oversees the process and mandates the sale
The guests confirm they bought Grindr directly as part of that forced sale timeline; it did not go to another buyer first[4:50]
Many traditional buyers and investors refused to participate because they did not want to be associated with gay sex or gay dating[5:08]
• They mention conservative investment committee members and potential Middle Eastern backers who declined due to stigma around gay sex and dating
Ultimately only three nontraditional private equity firms submitted legitimate bids, and the guests partnered with another PE firm to buy the company[5:16]

Why Grindr was an attractive, mispriced asset

Latent homophobia and multiple perceived problems

They were surprised by how many firms that had helped Tinder did not want to touch Grindr, revealing latent homophobia in the process[5:41]
They say they benefited from this homophobia because it kept competition and pricing down for what they saw as an incredible business[5:41]
Grindr also had several other problems that scared private equity: public privacy/data issues, lawsuits over alleged HIV data sales, Chinese ownership and CFIUS involvement, PR problems, and stigma[6:03]
• They note that Grindr was one of the first cases where CFIUS retroactively unwound an existing deal; they contrast this with CFIUS's attempts regarding TikTok

Underlying business strength and user love

Despite these issues, the guests were in love with the business fundamentals: it was growing fast, very profitable, and users loved the core product[6:01]
They emphasize that customer frustration often stemmed from sloppy product work and customer care rather than lack of product-market fit[7:15]
• They characterize Grindr's mistakes as typical of small businesses where growth outruns internal capacity, leading to lagging product, legal, and operational systems
Both guests had prior experience at large companies, so they understood the complexity of scaling from ~5 million to 20 million users and the legal and accounting shifts involved[6:47]

Evidence of under-management and upside

They saw shocking metrics like a 1.8 App Store rating, which they interpret as essentially 0.8 out of 5 because one star is the minimum[7:13]
• They also point out a management rating of about 19% on Glassdoor, which one guest had never seen so low
At the same time, Grindr was doing around $100 million in revenue and $45 million in profit despite those terrible ratings[8:38]
• They concluded from this mismatch-strong cash flow, iconic brand, bad ratings-that the company was severely under-managed and represented a big opportunity for operational improvement

Deal terms, financing, and risk-taking on the acquisition

Purchase price, valuation, and discount

They bought Grindr for about $600 million (sometimes described as roughly $600-650 million) when it was generating about $45 million of EBITDA[8:41]
• This implied a purchase multiple of roughly 12-13x EBITDA, which they say was under market compared to public comps trading around 20x, though private companies warrant a discount
One guest estimates that stigma likely created at least a 50% discount versus what a comparable straight dating app with similar metrics might have fetched[8:16]

Capital structure and earn-out mechanics

The $600 million deal was structured as about $200 million of equity, $200 million of debt (from Fortress), and another $200 million as an earn-out due upon exit to the prior owner[16:10]
Only $200 million of equity actually went in up front, which is key to the eventual return on equity calculation[16:30]
They took Grindr public on the New York Stock Exchange at a $2 billion valuation roughly two and a half years after buying it[20:39]
• Because the first $200 million at exit went to the seller via the earn-out and the debt stayed on the business, about $1.8 billion of equity value remained, implying roughly a 9x return on the original $200 million equity

Role of debt and similarities to real estate leverage

They explain that in private equity, unlike startups, debt is a powerful multiplier because it is cheaper than equity even when it seems expensive[17:30]
One guest compares buying companies with leverage to buying a house or apartment building: you combine leverage and cash, sometimes refinance later, and structure layers of debt with different time horizons[17:21]
They note their tax lawyer is crucial in creatively restructuring deals so different investors and lenders can participate under their own constraints[17:22]

Effort to raise $600M vs. smaller amounts

One guest argues it is roughly the same amount of work to raise $1 million, $10 million, $100 million, or $600 million; the main difference is the type of players and questions involved[17:09]
With Grindr, traditional channels for debt and equity were largely closed due to stigma, so they turned to alternative debt, family offices, and nontraditional banks and lawyers willing to work on the deal[17:49]

Emotional experience and stress of taking on Grindr

COVID shock and worse-than-expected realities

While the deal was halfway closed, COVID hit, which was particularly bad for a location-based physical meet-up product like Grindr[12:32]
User activity dropped by 20-30% when lockdowns started, and the guests had been planning to live at least part-time in LA but were disrupted[12:39]
After closing, they found many aspects of the business were "much worse" than they had expected when they saw the full data[12:24]

Personal toll and emotional leveling

One guest says over 2.5 years he gained about 25 pounds, his cholesterol went up 30%, and he rarely saw his kids due to the stress and workload[12:51]
Despite the toll, he nostalgically looks back fondly on the experience and felt it was the most rewarding product work he had ever done[12:58]
He describes losing his "super happy gene" and "super distressed gene" after many startups; he no longer fully trusts emotional highs or lows and tries to stay more level[13:07]
• He had written that he has become distrustful of moments that feel too good or too low, and that this emotional leveling helps him focus and persist when others might quit or get sidetracked
His co-founder sometimes has to remind him to celebrate milestones, like at the NYSE when Grindr went public and he struggled to feel the expected joy[13:54]
He recalls expecting a life-changing feeling when receiving a $700,000 wire from a Google acquisition, but instead feeling mostly relief and resignation[14:13]

Operational turnaround at Grindr: talent, tech, product, and mission

Cultural problems and talent overhaul

They discovered that under Chinese ownership, the culture was "ruled by fear" and opaque, with only a handful of people having equity or real knowledge of what was going on[21:49]
Engineering talent was not very good and not committed to the company or the community it served[22:15]
They ended up firing about 70% of the staff, mostly on the engineering side, which was deeper than they had anticipated before taking over[21:49]
They structured the turnaround in three serial phases: reset the talent, fix the tech stack, and then rebuild the product and drive revenue[22:46]

Understanding user issues and importing scale experience

One guest had already talked to hundreds of customers during diligence, read thousands of customer care tickets, and combed Reddit forums to catalog issues before closing the deal[23:35]
Many original employees had deep domain knowledge but lacked experience scaling systems (e.g., moderation across 193 countries and multiple languages)[23:57]
• He had previously dealt with similar problems at Yahoo Mail, so he knew how to handle large-scale moderation, legal complexities, and global user bases and brought engineers from Yahoo with that experience

Key hire in privacy and safety and lawsuit resolution

They recruited Yahoo's former head of global privacy and safety, a gay man who had retired, to lead these functions at Grindr[24:32]
• When told the company was Grindr, he agreed to come out of retirement, saying he wanted to do something for the community
At that time, Grindr was being sued by 13 U.S. state attorneys general over alleged privacy and data leakage, especially about HIV-related data[24:59]
On a first call with the 13 attorneys general, many already knew this hire from his Yahoo days; when they learned he was now at Grindr, 12 of the 13 essentially said they were comfortable because "Shane's there" and the company was now run by professionals[25:26]
The feature at issue was the profile field "what's your HIV status?" which they say actually saved 10,000+ lives a year by informing safer encounters[25:07]

Diversity, mission, and recruiting superpower

Some employees initially perceived that the new straight male leaders were just bringing in their friends, but by the time they left, about 70% of hires were from minority groups, particularly the LGBTQ community[26:05]
They used Grindr's mission and impact to recruit high-caliber talent who believed in serving the LGBTQ community globally[26:41]
They argue that most sexual health and safety information about gay sex and trans healthcare outside English comes from Grindr, which publishes in 57 languages[27:05]
• For example, a closeted trans person in India seeking a vaccine-friendly doctor could use a database funded and built by Grindr
They claim Grindr saves lives at a rate that Tinder never will, through education on safety, HIV status, and support for closeted people seeking community and information[27:41]

Why they pursued private equity instead of traditional VC or repeated startups

View of entrepreneurship vs. private equity

One guest says when people say they want to be entrepreneurs he thinks, "good God, why?" because startups cause stress, gray hair, and family sacrifices[28:36]
He loves entrepreneurship but fears the lack of control over how long a startup will take-possibly 12-15 years-more than the 100-hour workweeks themselves[29:57]
Private equity still has uncertainty but with shorter, more defined timeframes; they would not intentionally enter a 10-year PE deal because the math does not work[30:36]

Crowded venture market and angel investing background

Most of their friends are venture capitalists or operators; each guest has done over 50 angel investments, with one holding 13 unicorns in his portfolio[30:55]
He notes that required dealflow is huge: he met with around 1,000 companies to invest in the 50 he liked, some of which worked out[31:40]
They view VC as crowded, with everyone chasing the same AI deals at inflated valuations and very long timelines before partners see significant returns[31:19]

Their chosen model: SPVs and operator-led PE

Instead of raising a large fund, they prefer SPVs (single-purpose vehicles) to raise money deal by deal for opportunities where they can add value[31:30]
They see private equity as combining their operator skills with investment skills to multiply capital with more control and less binary risk than startups[32:43]
They underscore that most startups die because there is no market appetite, not because of execution, whereas PE focuses on businesses with product-market fit and stable cash flows[32:35]

How to source and structure mid-market private equity deals

Deal sourcing from networks and VC portfolios

They suggest sourcing PE deals through personal networks: profitable businesses with owners who want to retire, are exhausted, or need to split up[33:09]
They also ask VC friends about portfolio companies that are good businesses but no longer venture-scale (e.g., growing 10-20% annually, not IPO-bound)[33:25]
Such companies may be second or third in their market, struggling with recruiting or looming challenges like AI, but still have solid brands and revenue[33:44]

JibJab example and smaller deal economics

They previously bought JibJab for about $20 million when it had roughly $5 million of EBITDA (about 4x EBITDA multiple)[41:37]
They put $15 million of debt on JibJab and only $5 million of equity; the business threw off enough cash to pay down the debt in about three years[41:49]
They then refinanced, borrowed another $15 million, bought out about half the investors, repaid that debt, and now largely treat JibJab as a cash-flow machine[42:13]
He illustrates that if five partners each put in $1 million for 20% ownership, a smaller PE deal can still be attractive without running the company directly[41:57]

Role of carry and when to operate directly

With Grindr's scale, the same equity check that bought a large share of JibJab bought a much smaller slice, but the 20% carry on $1.6+ billion of value creation is huge[42:45]
Because Grindr was so significant, they decided to run it themselves (CEO and COO), whereas for JibJab they rely on an outside CEO and act more as board-level operators[43:27]
They note another model is to centralize operations (e.g., marketing, customer care) across multiple acquired businesses, similar to IAC or Bending Spoons' app portfolio strategy[43:31]

Risk reduction focus in PE vs. angel investing

They stress that without a fund and with fewer deals, PE requires a different mindset: focus on risk reduction more than upside modeling[37:44]
In angel investing, they accept many zeros and rely on a few big winners; in PE, each deal must likely return at least 1-2x with a low chance of permanent loss[38:35]
They spend most of their analytical time on what can go wrong rather than optimistic scenarios, likening the role to a chief risk officer[38:58]

Practical advice on what businesses to buy and how to think about AI/crypto disruption

Guidance to a hypothetical nephew entering PE-style deals

Asked what he'd advise a nephew considering bookkeeping, brokerage, or AI-related businesses, one guest says he loves AI and crypto but would only pursue them if the nephew had real expertise[43:50]
Absent that, he would guide the nephew toward finding an existing business with stable cash flow and recurring revenue (including consumer subscriptions) where the owner is ready to exit[45:04]
The ideal is a business where you can layer on debt, buy in at a reasonable multiple, and have a credible thesis to double revenue over 3-5 years and exit at a higher multiple, yielding a 5-10x return[45:35]
He emphasizes first ensuring cash flow is stable enough to repay debt, then only entering if you have a solid, specific thesis on how to increase revenue[45:04]

Their revenue growth thesis at Grindr

They doubled Grindr's revenue from about $100 million to $200 million in two and a half years[46:32]
Their thesis combined cleaning up talent and tech with applying the "Tinder playbook": better monetization features, pricing optimization, and product improvements[46:57]
Concrete levers included fixing weak buy-buttons and flows, adding a web version, implementing a Boost-like feature, and tailoring prices by market instead of a flat global pricing scheme[47:32]
They also planned to cut underperforming ad revenue that users hated while growing higher-value subscription and in-product revenue, plus improving retention and reducing uninstalls[47:46]
They built a model assigning expected percentage gains to each initiative; the total suggested about a 3x revenue potential, so they were confident they could at least double[47:17]

Views on AI, crypto, healthcare, and new venture Agency

Macro thesis: disruption zones

They see crypto and AI as major sources of disruption that can transform or destabilize traditionally stable spaces, which complicates PE in those areas in the near term[50:20]
From a venture perspective, however, these same disruptions are ideal for investment because they will likely generate significant new wealth over the next decade despite short-term valuation bubbles[51:00]
They argue that AI works particularly well in domains with extensive documentation and high value, such as legal, engineering, and medical fields[51:26]
They also highlight entertainment as a target but note that its IP protection and legal complexities have historically slowed disruption[51:57]

Impact of Apple privacy changes on consumer businesses

They note that Apple's iOS 14 changes, which limited data access for Facebook, broke acquisition economics for many small and medium consumer businesses[52:38]
Companies that had been able to acquire customers effectively on Facebook and Google suddenly struggled or became unprofitable, which in turn affected PE evaluations of consumer deals[53:00]

Agency: connecting AI agents with traditional web commerce

One guest describes working with entrepreneurs on AI ideas and realizing a missing piece: agents lack a practical way to interact with the existing web to complete complex tasks[53:23]
He dislikes the idea of separate LLMs embedded into every website and instead envisions a few powerful consumer agents that act on the user's behalf across many sites[53:53]
He expects people to ask an agent to, for example, research and buy a mountain bike, with the agent negotiating and executing on various vendor sites[54:29]
Currently, systems like Mariner and Operator attempt to click around websites programmatically but are inefficient; traditional commerce sites are not built for agents[54:52]
Agency (spelled A-I-G-E-N-C-Y) is conceived as the glue layer: when a site receives traffic from an AI agent (e.g., from OpenAI), it redirects that to an intermediate agent that speaks "agent-to-agent" with consumer agents[55:33]
This intermediary agent is not user-facing; it helps traditional web 2.0 businesses connect their inventory and actions to AI-driven commerce without each hiring scarce AI engineers[56:25]

Career reflections, famous founders, and the role of luck and partners

Would they have done PE at 25?

Asked if he would have done PE at 25, one guest says no; Grindr worked because they could apply 25 years of accumulated experience[57:51]
He believes early career should focus on gaining experience, building networks, and seeing many "movies" play out before tackling big PE opportunities[57:55]

Freshmen and seniors vs. sophomores and juniors in startups

They cite the notion that "freshmen and seniors" (very inexperienced or very experienced founders) tend to make the most money in startups[58:30]
Freshmen don't know the rules and thus break them productively; seniors know the rules deeply and exploit market weaknesses; mid-level people often underperform in founding roles[58:34]
As investors, they are cautious about founders who are mid-level directors from big tech companies; they prefer either scrappy young founders or deeply experienced industry experts[59:47]

Examples of early encounters with major founders

One guest recalls doing his first deal with Travis Kalanick when Travis ran Scour and he ran iDrive; they combined iDrive's large MP3 collection with Scour's powerful media search[1:01:15]
He describes Travis as incredibly difficult to do business with but supported by a very talented team and excellent technology[1:01:32]
He also knew the founders of Zobny in the same dorm as Dropbox's Drew, and he spent time with Jack Dorsey when Twitter was failing and attempted to buy it for $19 million at Yahoo[1:02:08]
He spoke to Brian Chesky when a VC was considering investing in Airbnb and liked the business but did not walk away thinking Brian was obviously a generational founder[1:03:32]
He argues that early genius is often not obvious: many of these founders were interesting but did not obviously stand out as destined billionaires in early meetings[1:03:19]

Correlation between talent, success, and luck

He notes that his most intelligent or talented friends are not always his richest; the overlap between talent and financial success is smaller than people assume[1:04:46]
He cites a VC who said the smartest people are probably right only about 30% of the time and normal smart people about 10%, but personal perception often overweights one's own hits[1:05:58]
He believes luck and timing-like when a bubble bursts relative to an exit-dramatically affect outcomes and shape later opportunities and confidence[1:05:54]
They advise aspiring entrepreneurs to commit to 20 years and multiple startups (four or five) to increase the chance that talent and luck will coincide[1:07:46]

Naval Ravikant, crypto, and long-view investing

One guest credits Naval Ravikant with getting him into angel investing and, over a decade ago, into crypto[1:14:49]
He recalls asking Naval, when Bitcoin was under $1,000, how big it could get; Naval said $1 million per Bitcoin "before we die" without specifying when[1:15:33]
He admires Naval's ability to look out decades and make accurate predictions, and admits he wishes he had bought more Bitcoin at the time[1:14:59]
Another anecdote: he once tried to sell a Porsche during a downturn and a buyer offered to pay in Bitcoin (well under $1,000 each), but he insisted on cash; he later calculated that accepting the Bitcoin would have made it a "$372 million Porsche"[1:20:42]

Emotional adoption curve and industries ripe for disruption

One guest previously wrote a 2006 presentation at Yahoo about the "emotional adoption curve," arguing that customer anger and frustration are the best predictors of disruptive change[1:17:53]
He lists finance/money, healthcare (especially in the U.S.), entertainment, telephony, and ultimately government as industries where opacity, monopolies, and customer anger make them ripe for internet-driven disruption[1:18:26]
He notes that social networks can add fuel to this anger, and while disruption can improve things, it can also sometimes yield worse outcomes even if incumbents were abusive[1:19:04]

Importance of partners and closing reflections

Choosing who to work with over decades

One guest highlights three key long-term collaborators: James Currier from HBS and Tickle, his co-guest Jeff as a product genius, and Naval as a big-brained thinker who shaped his investing and crypto journey[1:20:26]
He says his value-add in those relationships is being the operator who ensures execution, complementing their high-level vision[1:22:04]
He endorses the philosophy that you become like the five people you spend the most time with, so you should choose collaborators you respect and want to emulate[1:21:48]

Unexpected trajectories: Mel Robbins example

He mentions Mel Robbins, now a huge podcaster, once worked as head of marketing at their startup Tickle in a basement office in Cambridge around 1999[1:22:39]
He only recently realized her later success when his wife listened to her podcast and he recognized her voice[1:22:36]

Final advice: find the right people and have fun

They are praised by the hosts for being consistent over decades, doing serious work while maintaining a sense of fun and lightness[1:21:19]
One guest closes by emphasizing that regardless of whether you do PE, VC, or startups, the work is hard, so it is crucial to find people you respect and enjoy spending hours with[1:21:52]
He says Jeff keeps him laughing all day but is also incredibly insightful and skilled, underscoring the value of a great partner[1:21:52]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Mispriced, stigmatized, or complicated assets can hide exceptional opportunities if the underlying product is loved and the cash flows are strong, especially when others are scared away by optics, regulation, or controversy.

Reflection Questions:

  • • What markets or products in your industry are currently avoided because of stigma, regulation, or perceived complexity, yet still have loyal users and strong revenue?
  • • How could you separate real, non-negotiable risks from superficial or emotional objections that keep competitors away from a promising opportunity?
  • • What specific research steps (customer interviews, reading complaints, digging into metrics) could you take this month to uncover an under-managed asset with strong fundamentals?
2

In private equity or later-stage acquisitions, disciplined risk reduction-understanding downside scenarios, debt coverage, and operational fragility-is more important than chasing optimistic upside cases.

Reflection Questions:

  • • Where in your current projects are you assuming things will go right instead of explicitly modeling what happens if key assumptions fail?
  • • How might your decision-making change if you forced yourself to write a one-page "downside memo" before committing to any major investment or initiative?
  • • What is one active business or investment you could review this week to stress test its cash flow resilience and debt load under a severe but plausible shock?
3

Aligning talent and culture with the mission-especially in community-driven products-can transform both performance and trust, but often requires hard choices about replacing misaligned teams and rebuilding systems.

Reflection Questions:

  • • Which roles or people in your organization are clearly misaligned with the mission or community you serve, and what is that misalignment costing you?
  • • How could you more deliberately recruit people who are both technically excellent and deeply connected to your customer base or cause?
  • • What one concrete change in team composition, leadership, or culture could you make in the next quarter to better reflect and serve your core users?
4

For experienced operators, buying and improving an existing profitable business can offer a more controllable, less binary path than starting from zero, especially when you have a clear playbook to grow revenue and fix operational gaps.

Reflection Questions:

  • • Given your current skills and experience, what type of existing business (industry, size, business model) could you realistically improve more than its current owner?
  • • How would your risk profile and lifestyle change if your next big move were an acquisition with stable cash flow rather than a greenfield startup?
  • • What is one concrete step you could take in the next 60 days to source potential acquisition targets from your network or local business community?
5

Emotional leveling-refusing to be seduced by highs or crushed by lows-helps founders and investors persist through long, stressful journeys and make clearer decisions under pressure.

Reflection Questions:

  • • Looking back at the last year, when did emotional highs or lows most distort your judgment or cause you to overreact?
  • • What specific practices (journaling, postmortems, checklists, external advisors) could you adopt to separate feelings from facts before major decisions?
  • • How might your behavior change if you consciously treated both big wins and big setbacks as temporary data points rather than verdicts on your identity?
6

Long-term success in entrepreneurship and investing is compounded by who you choose to work with; surrounding yourself with high-caliber, values-aligned people you enjoy accelerates learning, resilience, and opportunity flow.

Reflection Questions:

  • • Who are the three to five people you currently spend the most professional time with, and how are they influencing your thinking and standards?
  • • In what ways could you be more intentional about seeking collaborators who complement your strengths (e.g., visionary vs. operator) rather than mirror them?
  • • What is one relationship-with a peer, mentor, or potential partner-you could invest in more deeply over the next six months that would likely raise your trajectory?

Episode Summary - Notes by Hayden

How two straight guys bought Grindr and made $2B
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