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SAHIL SAPRU

SAHIL SAPRU

3 years ago

How I grew my business to a $5 million annual recurring revenue

More on Entrepreneurship/Creators

cdixon

cdixon

3 years ago

2000s Toys, Secrets, and Cycles

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.


Full article is available here

Jared Heyman

Jared Heyman

2 years ago

The survival and demise of Y Combinator startups

I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.

Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.

Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.

As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.

YC startups by status after 12 years:

Half the startups have failed, over one-third have exited, and the rest are still operating.

In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.

Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.

I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.

Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.

YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

Eve Arnold

Eve Arnold

3 years ago

Your Ideal Position As a Part-Time Creator

Inspired by someone I never met

Photo by Nubelson Fernandes

Inspiration is good and bad.

Paul Jarvis inspires me. He's a web person and writer who created his own category by being himself.

Paul said no thank you when everyone else was developing, building, and assuming greater responsibilities. This isn't success. He rewrote the rules. Working for himself, expanding at his own speed, and doing what he loves were his definitions of success.

Play with a problem that you have

The biggest problem can be not recognizing a problem.

Acceptance without question is deception. When you don't push limits, you forget how. You start thinking everything must be as it is.

For example: working. Paul worked a 9-5 agency work with little autonomy. He questioned whether the 9-5 was a way to live, not the way.

Another option existed. So he chipped away at how to live in this new environment.

Don't simply jump

Internet writers tell people considering quitting 9-5 to just quit. To throw in the towel. To do what you like.

The advice is harmful, despite the good intentions. People think quitting is hard. Like courage is the issue. Like handing your boss a resignation letter.

Nope. The tough part comes after. It’s easy to jump. Landing is difficult.

The landing

Paul didn't quit. Intelligent individuals don't. Smart folks focus on landing. They imagine life after 9-5.

Paul had been a web developer for a long time, had solid clients, and was respected. Hence if he pushed the limits and discovered another route, he had the potential to execute.

Working on the side

Society loves polarization. It’s left or right. Either way. Or chaos. It's 9-5 or entrepreneurship.

But like Paul, you can stretch polarization's limits. In-between exists.

You can work a 9-5 and side jobs (as I do). A mix of your favorites. The 9-5's stability and creativity. Fire and routine.

Remember you can't have everything but anything. You can create and work part-time.

My hybrid lifestyle

Not selling books doesn't destroy my world. My globe keeps spinning if my new business fails or if people don't like my Tweets. Unhappy algorithm? Cool. I'm not bothered (okay maybe a little).

The mix gives me the best of both worlds. To create, hone my skill, and grasp big-business basics. I like routine, but I also appreciate spending 4 hours on Saturdays writing.

Some days I adore leaving work at 5 pm and disconnecting. Other days, I adore having a place to write if inspiration strikes during a run or a discussion.

I’m a part-time creator

I’m a part-time creator. No, I'm not trying to quit. I don't work 5 pm - 2 am on the side. No, I'm not at $10,000 MRR.

I work part-time but enjoy my 9-5. My 9-5 has goodies. My side job as well.

It combines both to meet my lifestyle. I'm satisfied.

Join the Part-time Creators Club for free here. I’ll send you tips to enhance your creative game.

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Jon Brosio

Jon Brosio

3 years ago

You can learn more about marketing from these 8 copywriting frameworks than from a college education.

Email, landing pages, and digital content

Photo by Ron Lach from Pexels

Today's most significant skill:

Copywriting.

Unfortunately, most people don't know how to write successful copy because they weren't taught in school.

I've been obsessed with copywriting for two years. I've read 15 books, completed 3 courses, and studied internet's best digital entrepreneurs.

Here are 8 copywriting frameworks that educate more than a four-year degree.

1. Feature — Advantage — Benefit (F.A.B)

This is the most basic copywriting foundation. Email marketing, landing page copy, and digital video ads can use it.

F.A.B says:

  • How it works (feature)

  • which is helpful (advantage)

  • What's at stake (benefit)

The Hustle uses this framework on their landing page to convince people to sign up:

Courtesy | Thehustle.co

2. P. A. S. T. O. R.

This framework is for longer-form copywriting. PASTOR uses stories to engage with prospects. It explains why people should buy this offer.

PASTOR means:

  • Problem

  • Amplify

  • Story

  • Testimonial

  • Offer

  • Response

Dan Koe's landing page is a great example. It shows PASTOR frame-by-frame.

Courtesy | Dan Koe

3. Before — After — Bridge

Before-after-bridge is a copywriting framework that draws attention and shows value quickly.

This framework highlights:

  • where you are

  • where you want to be

  • how to get there

Works great for: Email threads/landing pages

Zain Kahn utilizes this framework to write viral threads.

Courtesy | Zain Kahn

4. Q.U.E.S.T

QUEST is about empathetic writing. You know their issues, obstacles, and headaches. This allows coverups.

QUEST:

  • Qualifies

  • Understands

  • Educates

  • Stimulates

  • Transitions

Tom Hirst's landing page uses the QUEST framework.

Courtesy | Tom Hirst

5. The 4P’s model

The 4P’s approach pushes your prospect to action. It educates and persuades quickly.

4Ps:

  • The problem the visitor is dealing with

  • The promise that will help them

  • The proof the promise works

  • push towards action

Mark Manson is a bestselling author, digital creator, and pop-philosopher. He's also a great copywriter, and his membership offer uses the 4P’s framework.

Courtesy | Mark Manson

6. Problem — Agitate — Solution (P.A.S)

Up-and-coming marketers should understand problem-agitate-solution copywriting. Once you understand one structure, others are easier. It drives passion and presents a clear solution.

PAS outlines:

  • The issue the visitor is having

  • It then intensifies this issue through emotion.

  • finally offers an answer to that issue (the offer)

The customer's story loops. Nicolas Cole and Dickie Bush use PAS to promote Ship 30 for 30.

Courtesy | ship30for30.com

7. Star — Story — Solution (S.S.S)

PASTOR + PAS = star-solution-story. Like PAS, it employs stories to persuade.

S.S.S. is effective storytelling:

  • Star: (Person had a problem)

  • Story: (until they had a breakthrough)

  • Solution: (That created a transformation)

Ali Abdaal is a YouTuber with a great S.S.S copy.

Courtesy | Ali Abdaal

8. Attention — Interest — Desire — Action

AIDA is another classic. This copywriting framework is great for fast-paced environments (think all digital content on Linkedin, Twitter, Medium, etc.).

It works with:

  • Page landings

  • writing on thread

  • Email

It's a good structure since it's concise, attention-grabbing, and action-oriented.

Shane Martin, Twitter's creator, uses this approach to create viral content.

Courtesy | Shane Martin

TL;DR

8 copywriting frameworks that teach marketing better than a four-year degree

  • Feature-advantage-benefit

  • Before-after-bridge

  • Star-story-solution

  • P.A.S.T.O.R

  • Q.U.E.S.T

  • A.I.D.A

  • P.A.S

  • 4P’s

Miguel Saldana

Miguel Saldana

3 years ago

Crypto Inheritance's Catch-22

Security, privacy, and a strategy!

How to manage digital assets in worst-case scenarios is a perennial crypto concern. Since blockchain and bitcoin technology is very new, this hasn't been a major issue. Many early developers are still around, and many groups created around this technology are young and feel they have a lot of life remaining. This is why inheritance and estate planning in crypto should be handled promptly. As cryptocurrency's intrinsic worth rises, many people in the ecosystem are holding on to assets that might represent generational riches. With that much value, it's crucial to have a plan. Creating a solid plan entails several challenges.

  • the initial hesitation in coming up with a plan

  • The technical obstacles to ensuring the assets' security and privacy

  • the passing of assets from a deceased or incompetent person

  • Legal experts' lack of comprehension and/or understanding of how to handle and treat cryptocurrency.

This article highlights several challenges, a possible web3-native solution, and how to learn more.

The Challenge of Inheritance:

One of the biggest hurdles to inheritance planning is starting the conversation. As humans, we don't like to think about dying. Early adopters will experience crazy gains as cryptocurrencies become more popular. Creating a plan is crucial if you wish to pass on your riches to loved ones. Without a plan, the technical and legal issues I barely mentioned above would erode value by requiring costly legal fees and/or taxes, and you could lose everything if wallets and assets are not distributed appropriately (associated with the private keys). Raising awareness of the consequences of not having a plan should motivate people to make one.

Controlling Change:

Having an inheritance plan for your digital assets is crucial, but managing the guts and bolts poses a new set of difficulties. Privacy and security provided by maintaining your own wallet provide different issues than traditional finances and assets. Traditional finance is centralized (say a stock brokerage firm). You can assign another person to handle the transfer of your assets. In crypto, asset transfer is reimagined. One may suppose future transaction management is doable, but the user must consent, creating an impossible loop.

  • I passed away and must send a transaction to the person I intended to deliver it to.

  • I have to confirm or authorize the transaction, but I'm dead.

In crypto, scheduling a future transaction wouldn't function. To transfer the wallet and its contents, we'd need the private keys and/or seed phrase. Minimizing private key exposure is crucial to protecting your crypto from hackers, social engineering, and phishing. People have lost private keys after utilizing Life Hack-type tactics to secure them. People that break and hide their keys, lose them, or make them unreadable won't help with managing and/or transferring. This will require a derived solution.

Legal Challenges and Implications

Unlike routine cryptocurrency transfers and transactions, local laws may require special considerations. Even in the traditional world, estate/inheritance taxes, how assets will be split, and who executes the will must be considered. Many lawyers aren't crypto-savvy, which complicates the matter. There will be many hoops to jump through to safeguard your crypto and traditional assets and give them to loved ones.

Knowing RUFADAA/UFADAA, depending on your state, is vital for Americans. UFADAA offers executors and trustees access to online accounts (which crypto wallets would fall into). RUFADAA was changed to limit access to the executor to protect assets. RUFADAA outlines how digital assets are administered following death and incapacity in the US.

A Succession Solution

Having a will and talking about who would get what is the first step to having a solution, but using a Dad Mans Switch is a perfect tool for such unforeseen circumstances. As long as the switch's controller has control, nothing happens. Losing control of the switch initiates a state transition.

Subway or railway operations are examples. Modern control systems need the conductor to hold a switch to keep the train going. If they can't, the train stops.

Enter Sarcophagus

Sarcophagus is a decentralized dead man's switch built on Ethereum and Arweave. Sarcophagus allows actors to maintain control of their possessions even while physically unable to do so. Using a programmable dead man's switch and dual encryption, anything can be kept and passed on. This covers assets, secrets, seed phrases, and other use cases to provide authority and control back to the user and release trustworthy services from this work. Sarcophagus is built on a decentralized, transparent open source codebase. Sarcophagus is there if you're unprepared.

Liam Vaughan

Liam Vaughan

3 years ago

Investors can bet big on almost anything on a new prediction market.

Kalshi allows five-figure bets on the Grammys, the next Covid wave, and future SEC commissioners. Worst-case scenario

On Election Day 2020, two young entrepreneurs received a call from the CFTC chairman. Luana Lopes Lara and Tarek Mansour spent 18 months trying to start a new type of financial exchange. Instead of betting on stock prices or commodity futures, people could trade instruments tied to real-world events, such as legislation, the weather, or the Oscar winner.

Heath Tarbert, a Trump appointee, shouted "Congratulations." "You're competing with 1840s-era markets. I'm sure you'll become a powerhouse too."

Companies had tried to introduce similar event markets in the US for years, but Tarbert's agency, the CFTC, said no, arguing they were gambling and prone to cheating. Now the agency has reversed course, approving two 24-year-olds who will have first-mover advantage in what could become a huge new asset class. Kalshi Inc. raised $30 million from venture capitalists within weeks of Tarbert's call, his representative says. Mansour, 26, believes this will be bigger than crypto.

Anyone who's read The Wisdom of Crowds knows prediction markets' potential. Well-designed markets can help draw out knowledge from disparate groups, and research shows that when money is at stake, people make better predictions. Lopes Lara calls it a "bullshit tax." That's why Google, Microsoft, and even the US Department of Defense use prediction markets internally to guide decisions, and why university-linked political betting sites like PredictIt sometimes outperform polls.

Regulators feared Wall Street-scale trading would encourage investors to manipulate reality. If the stakes are high enough, traders could pressure congressional staffers to stall a bill or bet on whether Kanye West's new album will drop this week. When Lopes Lara and Mansour pitched the CFTC, senior regulators raised these issues. Politically appointed commissioners overruled their concerns, and one later joined Kalshi's board.

Will Kanye’s new album come out next week? Yes or no?

Kalshi's victory was due more to lobbying and legal wrangling than to Silicon Valley-style innovation. Lopes Lara and Mansour didn't invent anything; they changed a well-established concept's governance. The result could usher in a new era of market-based enlightenment or push Wall Street's destructive tendencies into the real world.

If Kalshi's founders lacked experience to bolster their CFTC application, they had comical youth success. Lopes Lara studied ballet at the Brazilian Bolshoi before coming to the US. Mansour won France's math Olympiad. They bonded over their work ethic in an MIT computer science class.

Lopes Lara had the idea for Kalshi while interning at a New York hedge fund. When the traders around her weren't working, she noticed they were betting on the news: Would Apple hit a trillion dollars? Kylie Jenner? "It was anything," she says.

Are mortgage rates going up? Yes or no?

Mansour saw the business potential when Lopes Lara suggested it. He interned at Goldman Sachs Group Inc., helping investors prepare for the UK leaving the EU. Goldman sold clients complex stock-and-derivative combinations. As he discussed it with Lopes Lara, they agreed that investors should hedge their risk by betting on Brexit itself rather than an imperfect proxy.

Lopes Lara and Mansour hypothesized how a marketplace might work. They settled on a "event contract," a binary-outcome instrument like "Will inflation hit 5% by the end of the month?" The contract would settle at $1 (if the event happened) or zero (if it didn't), but its price would fluctuate based on market sentiment. After a good debate, a politician's election odds may rise from 50 to 55. Kalshi would charge a commission on every trade and sell data to traders, political campaigns, businesses, and others.

In October 2018, five months after graduation, the pair flew to California to compete in a hackathon for wannabe tech founders organized by the Silicon Valley incubator Y Combinator. They built a website in a day and a night and presented it to entrepreneurs the next day. Their prototype barely worked, but they won a three-month mentorship program and $150,000. Michael Seibel, managing director of Y Combinator, said of their idea, "I had to take a chance!"

Will there be another moon landing by 2025?

Seibel's skepticism was rooted in America's historical wariness of gambling. Roulette, poker, and other online casino games are largely illegal, and sports betting was only legal in a few states until May 2018. Kalshi as a risk-hedging platform rather than a bookmaker seemed like a good idea, but convincing the CFTC wouldn't be easy. In 2012, the CFTC said trading on politics had no "economic purpose" and was "contrary to the public interest."

Lopes Lara and Mansour cold-called 60 Googled lawyers during their time at Y Combinator. Everyone advised quitting. Mansour recalls the pain. Jeff Bandman, a former CFTC official, helped them navigate the agency and its characters.

When they weren’t busy trying to recruit lawyers, Lopes Lara and Mansour were meeting early-stage investors. Alfred Lin of Sequoia Capital Operations LLC backed Airbnb, DoorDash, and Uber Technologies. Lin told the founders their idea could capitalize on retail trading and challenge how the financial world manages risk. "Come back with regulatory approval," he said.

In the US, even small bets on most events were once illegal. Under the Commodity Exchange Act, the CFTC can stop exchanges from listing contracts relating to "terrorism, assassination, war" and "gaming" if they are "contrary to the public interest," which was often the case.

Will subway ridership return to normal? Yes or no?

In 1988, as academic interest in the field grew, the agency allowed the University of Iowa to set up a prediction market for research purposes, as long as it didn't make a profit or advertise and limited bets to $500. PredictIt, the biggest and best-known political betting platform in the US, also got an exemption thanks to an association with Victoria University of Wellington in New Zealand. Today, it's a sprawling marketplace with its own subculture and lingo. PredictIt users call it "Rules Cuck Panther" when they lose on a technicality. Major news outlets cite PredictIt's odds on Discord and the Star Spangled Gamblers podcast.

CFTC limits PredictIt bets to $850. To keep traders happy, PredictIt will often run multiple variations of the same question, listing separate contracts for two dozen Democratic primary candidates, for example. A trader could have more than $10,000 riding on a single outcome. Some of the site's traders are current or former campaign staffers who can answer questions like "How many tweets will Donald Trump post from Nov. 20 to 27?" and "When will Anthony Scaramucci's role as White House communications director end?"

According to PredictIt co-founder John Phillips, politicians help explain the site's accuracy. "Prediction markets work well and are accurate because they attract people with superior information," he said in a 2016 podcast. “In the financial stock market, it’s called inside information.”

Will Build Back Better pass? Yes or no?

Trading on nonpublic information is illegal outside of academia, which presented a dilemma for Lopes Lara and Mansour. Kalshi's forecasts needed to be accurate. Kalshi must eliminate insider trading as a regulated entity. Lopes Lara and Mansour wanted to build a high-stakes PredictIt without the anarchy or blurred legal lines—a "New York Stock Exchange for Events." First, they had to convince regulators event trading was safe.

When Lopes Lara and Mansour approached the CFTC in the spring of 2019, some officials in the Division of Market Oversight were skeptical, according to interviews with people involved in the process. For all Kalshi's talk of revolutionizing finance, this was just a turbocharged version of something that had been rejected before.

The DMO couldn't see the big picture. The staff review was supposed to ensure Kalshi could complete a checklist, "23 Core Principles of a Designated Contract Market," which included keeping good records and having enough money. The five commissioners decide. With Trump as president, three of them were ideologically pro-market.

Lopes Lara, Mansour, and their lawyer Bandman, an ex-CFTC official, answered the DMO's questions while lobbying the commissioners on Zoom about the potential of event markets to mitigate risks and make better decisions. Before each meeting, they would write a script and memorize it word for word.

Will student debt be forgiven? Yes or no?

Several prediction markets that hadn't sought regulatory approval bolstered Kalshi's case. Polymarket let customers bet hundreds of thousands of dollars anonymously using cryptocurrencies, making it hard to track. Augur, which facilitates private wagers between parties using blockchain, couldn't regulate bets and hadn't stopped users from betting on assassinations. Kalshi, by comparison, argued it was doing everything right. (The CFTC fined Polymarket $1.4 million for operating an unlicensed exchange in January 2022. Polymarket says it's now compliant and excited to pioneer smart contract-based financial solutions with regulators.

Kalshi was approved unanimously despite some DMO members' concerns about event contracts' riskiness. "Once they check all the boxes, they're in," says a CFTC insider.

Three months after CFTC approval, Kalshi announced funding from Sequoia, Charles Schwab, and Henry Kravis. Sequoia's Lin, who joined the board, said Tarek, Luana, and team created a new way to invest and engage with the world.

The CFTC hadn't asked what markets the exchange planned to run since. After approval, Lopes Lara and Mansour had the momentum. Kalshi's March list of 30 proposed contracts caused chaos at the DMO. The division handles exchanges that create two or three new markets a year. Kalshi’s business model called for new ones practically every day.

Uncontroversial proposals included weather and GDP questions. Others, on the initial list and later, were concerning. DMO officials feared Covid-19 contracts amounted to gambling on human suffering, which is why war and terrorism markets are banned. (Similar logic doomed ex-admiral John Poindexter's Policy Analysis Market, a Bush-era plan to uncover intelligence by having security analysts bet on Middle East events.) Regulators didn't see how predicting the Grammy winners was different from betting on the Patriots to win the Super Bowl. Who, other than John Legend, would need to hedge the best R&B album winner?

Event contracts raised new questions for the DMO's product review team. Regulators could block gaming contracts that weren't in the public interest under the Commodity Exchange Act, but no one had defined gaming. It was unclear whether the CFTC had a right or an obligation to consider whether a contract was in the public interest. How was it to determine public interest? Another person familiar with the CFTC review says, "It was a mess." The agency didn't comment.

CFTC staff feared some event contracts could be cheated. Kalshi wanted to run a bee-endangerment market. The DMO pushed back, saying it saw two problems symptomatic of the asset class: traders could press government officials for information, and officials could delay adding the insects to the list to cash in.

The idea that traders might manipulate prediction markets wasn't paranoid. In 2013, academics David Rothschild and Rajiv Sethi found that an unidentified party lost $7 million buying Mitt Romney contracts on Intrade, a now-defunct, unlicensed Irish platform, in the runup to the 2012 election. The authors speculated that the trader, whom they dubbed the “Romney Whale,” may have been looking to boost morale and keep donations coming in.

Kalshi said manipulation and insider trading are risks for any market. It built a surveillance system and said it would hire a team to monitor it. "People trade on events all the time—they just use options and other instruments. This brings everything into the open, Mansour says. Kalshi didn't include election contracts, a red line for CFTC Democrats.

Lopes Lara and Mansour were ready to launch kalshi.com that summer, but the DMO blocked them. Product reviewers were frustrated by spending half their time on an exchange that represented a tiny portion of the derivatives market. Lopes Lara and Mansour pressed politically appointed commissioners during the impasse.

Tarbert, the chairman, had moved on, but Kalshi found a new supporter in Republican Brian Quintenz, a crypto-loving former hedge fund manager. He was unmoved by the DMO's concerns, arguing that speculation on Kalshi's proposed events was desirable and the agency had no legal standing to prevent it. He supported a failed bid to allow NFL futures earlier this year. Others on the commission were cautious but supportive. Given the law's ambiguity, they worried they'd be on shaky ground if Kalshi sued if they blocked a contract. Without a permanent chairman, the agency lacked leadership.

To block a contract, DMO staff needed a majority of commissioners' support, which they didn't have in all but a few cases. "We didn't have the votes," a reviewer says, paraphrasing Hamilton. By the second half of 2021, new contract requests were arriving almost daily at the DMO, and the demoralized and overrun division eventually accepted defeat and stopped fighting back. By the end of the year, three senior DMO officials had left the agency, making it easier for Kalshi to list its contracts unimpeded.

Today, Kalshi is growing. 32 employees work in a SoHo office with big windows and exposed brick. Quintenz, who left the CFTC 10 months after Kalshi was approved, is on its board. He joined because he was interested in the market's hedging and risk management opportunities.

Mid-May, the company's website had 75 markets, such as "Will Q4 GDP be negative?" Will NASA land on the moon by 2025? The exchange recently reached 2 million weekly contracts, a jump from where it started but still a small number compared to other futures exchanges. Early adopters are PredictIt and Polymarket fans. Bets on the site are currently capped at $25,000, but Kalshi hopes to increase that to $100,000 and beyond.

With the regulatory drawbridge down, Lopes Lara and Mansour must move quickly. Chicago's CME Group Inc. plans to offer index-linked event contracts. Kalshi will release a smartphone app to attract customers. After that, it hopes to partner with a big brokerage. Sequoia is a major investor in Robinhood Markets Inc. Robinhood users could have access to Kalshi so that after buying GameStop Corp. shares, they'd be prompted to bet on the Oscars or the next Fed commissioner.

Some, like Illinois Democrat Sean Casten, accuse Robinhood and its competitors of gamifying trading to encourage addiction, but Kalshi doesn't seem worried. Mansour says Kalshi's customers can't bet more than they've deposited, making debt difficult. Eventually, he may introduce leveraged bets.

Tension over event contracts recalls another CFTC episode. Brooksley Born proposed regulating the financial derivatives market in 1994. Alan Greenspan and others in the government opposed her, saying it would stifle innovation and push capital overseas. Unrestrained, derivatives grew into a trillion-dollar industry until 2008, when they sparked the financial crisis.

Today, with a midterm election looming, it seems reasonable to ask whether Kalshi plans to get involved. Elections have historically been the biggest draw in prediction markets, with 125 million shares traded on PredictIt for 2020. “We can’t discuss specifics,” Mansour says. “All I can say is, you know, we’re always working on expanding the universe of things that people can trade on.”

Any election contracts would need CFTC approval, which may be difficult with three Democratic commissioners. A Republican president would change the equation.