"Uber started as a ride-hailing service and received a threat from the New York City mayor, who wanted to ban it because the taxi medallion system and Yellow Cab fleet were effectively protected by a union or guild of taxi drivers with political power pushing back against Uber. In contrast, Uber positioned itself as a fairer platform that allowed people of any income level, any minority group, and at any time of day to access ride-hailing services, unlike the regulated Yellow Cab fleet." - Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast


"Another thing to consider is whether a startup will ask for permission or beg for forgiveness as it scales. In a given jurisdiction, can it work with regulators or not? Can it mobilize grassroots customer support to lobby on its behalf? What is the narrative disrupting incumbents or challenging competition? Is the press a viable counterattack against legislators? What are the existing laws, and what are the consequences of breaking them? No penalty, a fine, jail, or even execution? These are the questions startup founders must think through." - Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast


"Whether you are a startup or a company, you must decide if you will proactively shape legislation and position yourself as the good actor who helps make policy happen. If you are becoming a Goliath, can you shape legislation in a way that benefits you, and can you start in test cases or cities that are friendliest, face the least opposition, and move the fastest? What is the inside game, what is the outside game, and how will you execute it?" - Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast

Jeremy Au explains how startups interact with regulation as they grow. He discusses how strong startups escape competition and gain monopoly-like advantages, which later trigger regulatory scrutiny. The conversation shows how incumbents shape regulation, how startups choose favorable jurisdictions, and why founders must decide whether to ask permission or ask for forgiveness. Examples from Uber, Airbnb, TikTok Shop, and DraftKings illustrate how regulation, politics, and customer mobilization shape startup outcomes.

02:07 Regulatory Capture: Jeremy explains how regulation often benefits incumbents, as large industries lobby governments to create rules that protect their position.

06:34 Regulatory Inaction as Opportunity: Many technologies expand faster than governments can regulate them, creating temporary windows for startups to grow.

07:32 Policy Testbeds: Startups often push for favorable regulation in startup-friendly jurisdictions first, then use those precedents to expand into other markets.

10:13 Uber’s Regulatory Playbook: Uber challenged taxi regulations by continuing operations, using the press, and mobilizing public opinion.

14:20 When Customers Cannot Vote: Platforms like Airbnb face political limits because their main users, tourists, cannot vote in local elections.

Peter Thiel—the founder of PayPal, Palantir, and Mithril Capital—likes to say in his book Zero to One (which is highly recommended) that all happy companies are different. Each one earns a monopoly by solving a unique problem. In contrast, all failed companies are the same: they fail to escape competition.

The corollary of that statement is that anyone who has a monopoly will pretend they are in incredible competition to avoid scrutiny. Conversely, anybody that has a lot of competition will pretend they are a monopoly in a pitch deck to attract investment.

A startup often begins as a "David versus Goliath" but strives to become a Goliath itself. It aims to become a billion-dollar company with high profitability margins because it has managed to earn a monopoly and monopoly profits. We see this with Google and Meta. Meta, for example, is under constant attack by the EU and the US because regulators argue these are monopolies that need to be legislated.

One of the big issues today is the scrutiny of acquisitions. Meta acquired Instagram, WhatsApp, and Oculus for VR headsets, but they find it difficult to acquire companies now because they are seen as a monopoly. Similarly, Apple is facing legislation to open up its App Store because critics argue it holds a monopoly over Apple devices.

It is important to distinguish between regulation and regulatory capture. George Stigler, winner of the 1982 Nobel Prize in Economics, stated that as a rule, regulation is acquired by the industry and is designed and operated primarily for its benefit. Bill Gurley, the Benchmark VC, famously shouted at an All-In Summit that "regulation is the friend of the incumbent."

The All-In Podcast—hosted by Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg—often discusses these themes. Bill Gurley described how Benchmark invested in a startup to provide free Wi-Fi across downtown areas, funded by advertising. In Philadelphia, they collided with the commercial interests of incumbents like Verizon and Comcast. These powerful lobbyists pushed through bills that made it impossible for the startup to operate, and those regulations eventually spread to other states.

Regulatory affairs are highly dependent on political structures. You can visualize this on a two-by-two axis:

• Democracy (one person, one vote) vs. Autocracy/Undemocratic (centralized power).
• Liberalism (freedom of speech and decentralized expression) vs. Centralization.

In a democracy like California, tech companies often advance policy through referendums or propositions. In contrast, in highly centralized economies like China, there is no point in polling citizens about AI policy; the playbook is dictated by the centralized party.

Startups often face "regulatory inaction," particularly in the APEC region where AI laws are still catching up. A startup must decide: do you ask for permission or beg for forgiveness as you scale?

• The Case of Handy: This cleaning service startup used independent contractors to avoid the costs of "W2" full-time employees. When Handy tried to offer a benefits package to these contractors, they faced resistance in Democrat-controlled cities. The logic was that if contractors get benefits, the power of unions and the value of formal employment decrease. Handy eventually secured approval in Republican states and cascaded that policy outward.
• The Case of Uber: In New York City, Mayor Bill de Blasio attempted to ban Uber to protect the taxi medallion fleet and unions. Uber fought back through the press and by mobilizing customers. They argued that yellow cabs primarily served wealthy areas, while Uber served minority and low-income neighborhoods. Public outcry eventually forced the city to back down.
• The Case of DiDi: Unlike Uber, when Chinese regulators told DiDi not to proceed with an American IPO, the company faced immediate consequences and eventually had to delist. There was no room for lobbying or a press counter-attack.
• The Case of TikTok Shop: In Indonesia, TikTok Shop was growing aggressively but was shut down for lacking a specific license. They eventually had to acquire Tokopedia from GoTo to continue operating.

Can you mobilize your customers? DraftKings and FanDuel successfully did this by informing their users—many of whom are influential swing voters—that politicians wanted to ban fantasy sports. This triggered a massive wave of emails to legislators.

However, this fails if your customers aren't voters. Airbnb is banned in Singapore and faces heavy restrictions in New York City. The primary supporters of Airbnb are landlords (who are a minority) and tourists (who do not vote). Since local populations are voting for lower housing costs, legislating against Airbnb becomes a popular political move.

Finally, startups that become "Goliaths" may proactively shape legislation to create barriers for others. Marc Andreessen of A16Z has expressed frustration with CEOs who support regulatory barriers to form a "cartel" of government-blessed AI vendors protected from open-source competition. This was a direct pushback against Sam Altman of OpenAI, who visited Singapore Management University (SMU) last year to advocate for collaborative AI legislation.