Not Boring by Packy McCormick
Not Boring by Packy McCormick
MainStreet (Audio)

MainStreet (Audio)

Welcome to the 886 newly Not Boring people who have joined us since Thursday! If you’re reading this but haven’t subscribed, join 14,729 smart, curious folks by subscribing here!

Today’s Not Boring is brought to you by…

Read on and I’ll tell you how they can send your startup $50k tomorrow.

Hi friends 👋,

Happy Thursday! This little newsletter and our band of smart, curious people just keeps growing.

There are a lot of new folks joining Not Boring every week, which has not yet ceased to be exhilarating. I don’t think it will. Because there are so many new faces, I want to give a quick reminder of what the weekly schedule looks like, specifically what I’m doing with Thursdays.

Every Monday, I write a deep dive on a large (and typically public) company. The past few weeks, I’ve written about Twitter, Tencent (x2), Stripe, SoftBank, and Zoom. This upcoming Monday, I’m writing about… 🤫

Thursdays are more experimental, and typically focused on smaller companies. Recently, I’ve written Not Boring Investment Memos on OZE and Swaypay, and I plan to do about one deal per month through the Not Boring Syndicate. Sometimes, I have guests come on to teach us about something I don’t know much about, like the Magnolia empire or Ringtones. And sometimes, I go behind the scenes to write about how I’m growing and monetizing Not Boring. 

Thursdays are Wild Cards. And today, I’m trying something new: a Sponsored Writeup. I want to tell you a little bit about how it works for a couple reasons:

  1. In case other people are figuring out how to monetize their small media business or creative project.

  2. So that we go into this eyes wide open. I need to make money to keep Not Boring going as my full-time thing, and I want to do it as transparently as possible. 

A few weeks ago, I sent you all an email asking me to tell me about yourselves so that I could figure out how to make money with Not Boring and let potential sponsors know who reads it. The results are in, and you’re an impressive bunch. I put together a Sponsor Deck with some of the stats and rates. You can check it out here.

I decided to go the sponsored route so that I can:

  1. Keep it free for everyone. I think newsletters are an incredible way to democratize knowledge. 

  2. Keep growing. I put too much damn time into writing each of these to only send to a small group of people. 

There are broadly two ways that I can make money from sponsorships: 

  1. Cost Per Impression (CPM): A company pays me to get its message in front of this group of smart, curious people based on how many people read it, and regardless of whether anyone clicks the button to learn more or sign up or buy. Most of the sponsorships will be CPM.  

  2. Cost Per Acquisition (CPA): A company pays me a certain amount for each person who signs up, subscribes to, or buys its product. For example, if I did a deal with Fictional Shirt Company at $100 CPA, and 90 of you bought shirts after clicking my link, Fictional Shirt Company would pay me $9,000. I’ll do these less often. 

Typically, CPM deals make more sense because there’s value to a company in getting in front of you even if you don’t buy immediately. There’s an idea in marketing that someone needs to see a product seven times before buying, and while the number might not be exactly seven, it’s rarely one. I’m certainly not going to put on a hard enough sell to bring that number down. I’d rather just expose you to products and companies I like (and often use myself), and if you’re interested, great! 

Sometimes, though, CPA deals just make sense. 

After I sent the survey out, and before I made the deck, Nick Abouzeid reached out to me. Nick worked at Product Hunt, AngelList, and was most recently a VC at Shrug Capital. He told me that he was leaving Shrug -- a dream job -- to go work for one of their portfolio companies, that he was interested in sponsoring Not Boring, and that we should chat. 

When we talked, Nick said that he was going to MainStreet because as one of their investors, he had so much fun telling the people about the product that he wanted to go do it full-time. He offered me a choice: CPM (at the rate I was asking for) or CPA. 

I chose CPA, because I agree with Nick. In telling you about MainStreet, I’m making money by giving you free money.

MainStreet is relevant for both startups and investors: 

  • Startups: MainStreet will get you a bunch of money the government owes you.

  • Investors: MainStreet is the type of unsexy but practical AI application that will create investment opportunities for years before the machines start turning us into paperclips.

Main Street: Free Money for Startups

I’m not going to bury the lede. If you’re a startup, MainStreet will make you money. Here’s how:

  1. You sign up and connect your payroll system. 

  2. MainStreet finds tax credits and incentives that apply to your business.

  3. MainStreet sends you money now. You don’t need to wait until April. 

  4. MainStreet makes money by keeping 20% of the money the government pays you. If you don’t get anything, they don’t get anything. 

On average, MainStreet finds its customers $51,000. Instead of waiting until April to get the cash, they can cash advance you what you’re earning real-time at 0% tomorrow -- interest rates are baked into the fees you were going to pay them anyway. It’s free money.

See How Much You're Owed

No deal with the devil, no gotcha. MainStreet is just solving for the fact that dealing with the government is opaque and annoying, and that most companies don’t want to deal with it themselves. 

Who is MainStreet for? If you’re a tech company that’s less than five years old and conducts some sort of activity in the US, you’ll typically qualify. It takes about 5 minutes to find out. Just plug in your payroll and credit card details and they do the rest automagically. 

If you’re a founder, impress your investors. If you’re an investor, help out your portfolio companies. If you’re a startup employee, be the hero by telling your finance team. And if you’re on the finance or HR team, become a revenue driver for the day! 

Nick was nice enough to give Not Boring readers a couple of extra benefits:

  • Instant Access: Get your cash within 24 hours vs. a few days

  • 25% off for life! Instead of paying MainStreet 20% of the money you receive, you only pay 15%

If you’re convinced and you just want to go save money now, get to it:

Get Your $50k

We’re also here to learn, so I want to go a little deeper into MainStreet the company. We can’t invest in this one (yet) because they’ve already raised from some great investors and are focused on building, but MainStreet’s story is cool because it seems so simple, but there’s a lot going on under the hood. 

Rebuilding MainStreet

MainStreet has been trying to give people money for no-brainers since the beginning, but it wasn’t always tax credits and incentives. When it launched a year ago, MainStreet offered to pay people $10,000 to leave the San Francisco Bay Area. (I’m sorry SF readers!)

MainStreet is founder and CEO Doug Ludlow’s third company. He previously founded Hipster and sold it to AOL, and The Happy Home Company, which he sold to Google. While at Google, he was Chief of Staff for SMB ads, and saw the challenges that small and medium businesses in the country had in attracting talent.  

His initial vision was to create 1 million jobs in suburban and rural communities by facilitating the transition to a remote work future, way back in November 2019, before it was cool. MainStreet would recruit and train employees who wanted to move out of SF into a smaller city or town and set up local hubs where remote workers could build a sense of community. 

He could not have been more right on the trend. When Coronavirus hit, it spurred the migration from cities like San Francisco, and MainStreet got a ton of demand from employees interested in relocating. But the company also received a ton of unexpected inbound: emails and calls from state and local governments trumpeting their incentive programs. 

Ludlow and his co-founders, Dan Lindquist and Daniel Griffin, decided to rebuild MainStreet to focus on getting startups some of that free government money. Despite the huge COVID-induced demand spike for the old model, the pivot makes sense. Running recruiting, training, and a nationwide network of co-working spaces is not nearly as scalable, profitable, or fun as building a tech-powered way to help companies find $50,000 in their metaphorical couch cushions. 

It sounds like a blast to get to do that for work every day, but when Nick told me about MainStreet, my first thought was: why won’t a bunch of companies just do this and drive each others’ fees into the ground? This is an awesome product, but is it a good business? 

After digging in, I’m coming around. 

DoNotPay for Startups

Back in April, when Coronavirus was fresh and unemployment was skyrocketing, I wrote about one of my favorite companies, DoNotPay.  

Do Not Pay is one of my favorite companies that I’ve discovered in the past year. Joshua Browder, a 23-year-old Stanford graduate and the son of Red Notice author Bill Browder, founded the company when he was 17 to help people in the UK get out of parking tickets.

Now, the company has expanded to the US, and handles everything from parking tickets to suing people and companies in small claims court. Last summer, it launched a virtual credit card that subscribers can enter when they’re signing up for free trials so that they’re not auto-charged when the trial expires.

Just last week, they launched a new product that allows subscribers to claim their unemployment payments at the press of a button. Filing for unemployment has been a nightmare for many. They desperately need the money, but they aren’t able to figure out the forms, the websites are overloaded, and they can’t get through when they try to call in. DoNotPay will handle all of that. It guides them through the claim form via a chat interface, submits the form for them, and in states that require a phone call, calls the unemployment office every hour until it gets through. Once benefits are approved, it also automatically handles the weekly certifications of unemployment necessary to keep receiving checks. It makes a painful process easy.

DoNotPay is so magical because it uses software to help people do all of the things that they should be doing but don’t because they don’t know how, they forget, or it’s too much of a pain in the ass. The more capabilities that DoNotPay adds, the more ludicrously cheap its $3/mo subscription seems. It works, because after all of the painful work of onboarding new capabilities and translating them to software, DoNotPay has almost zero marginal costs.

MainStreet is DoNotPay for startups. 

Think about it. Finding, applying for, and keeping up to date with tax credits and incentives is a time-consuming, annoying, labor-intensive process for any company that wants to do it one-off. Breather, where I used to work, is HQ’ed in Canada and is therefore eligible for Canada’s sweet, sweet SRED credits, which essentially paid like 60% of our engineering and product teams’ salaries (don’t quote me on the exact number, but it was that unbelievable). It was an amazing benefit and a main reason that we did engineering there, but it was a pain in the ass. Our finance and legal teams spent weeks applying for and following up on SRED credits. 

But applying for tax credits and incentives is a job that’s perfectly suited for software. It’s repetitive, boring, and rules-based. Chances are that no one on your small team loves or has time for the process of finding and applying for tax credits, or continuing to update and submit paperwork any time new credits are added or you hire more people. Software loves that shit. 

MainStreet doesn’t really talk about the fact that it’s an AI company, but Gradient Ventures led its $2.3 million seed round in June. Gradient is Google’s early-stage fund that invests in AI companies. When you think about Artificial Intelligence, depending on where you fall in the “Child to Futurist Philosopher” spectrum, you probably think of movie robots like Wall-E or Goal Seek functions gone wild like Nick Bostrom’s paperclip maximizers. But for now, the most practical applications of AI are being built by companies like MainStreet that use machine learning to automate things that humans either can’t or don’t want to do. 

A few examples in Gradient’s portfolio: 

  • AllyO automates recruiting workflows

  • Anvil automates tedious paperwork 

  • Back enables internal service teams to automate employee requests (if AI were sentient, it would have told Back’s founders to pick a more easily searchable name)

Boring. None of these companies is building anything hyper-futuristic. What they and MainStreet all have in common is that they help businesses handle repetitive tasks more consistently, and get smarter and more valuable the more they do those tasks and the more new tasks they add. 

Which brings us back to MainStreet. Today, MainStreet gets you money in a few ways: 

  • R&D Credits: up to $250k/year

  • Hiring and Company Expansion Credits: up to $1,000 per new hire

  • Training and Workforce Development Credits: up to $5,000 per employee

Just Give Me My Money

Over time, it will add more and more state and local tax credits and incentives, and apply them to your business automatically. Just by having your payroll and credit card hooked up, MainStreet will constantly be on the lookout for ways to take money from the government and give it back to you. 

Getting all of those credits and incentives onboarded is a schlep -- there’s a lot of manual work people on the MainStreet team need to do to get them set up and to deal with the back and forth with the government entities involved. But unlike your company, which has to do all of that work to get money just for your company, MainStreet scales that upfront work across all of the companies it works with. That’s its compounding advantage over time: 

  • Do the hard work to find and connect credits and incentives manually

  • Acquire customers and save them money

  • Automatically scan and apply existing credits and incentives in the system to your company

  • Add more tax credits and incentives

  • Automatically scan and apply existing credits and incentives in the system to your company

  • And on and on… 

Like Stripe or Agora, MainStreet customers get the benefit of any software improvements or new credits without having to do anything. Unlike Stripe or Agora, the benefit to MainStreet’s improvements is more cash directly in your bank account. 

In addition to Gradient, MainStreet is backed by an all-star lineup of early stage investors including Ryan Hoover’s Weekend Fund, Shrug Capital, SV Angel, Remote First Capital, Basement Fund, Basecamp Ventures, Backend Capital, and a lot of angels. 

Its customers, including Sandbox VR, Italic, and Pipe, sing its praises, and I really think you will too. I want to hire a team just so I can use it myself.

Just yesterday, MainStreet’s CEO tweeted that the company has now saved startups and SMBs over $15 million in its short life.

I’m really excited to partner with MainStreet to give you money. It’s a no-brainer. 

Be the hero. Get your company its money back. Sign up, connect your payroll and CC, and see how much MainStreet sends your business.

Sign Up for MainStreet

If you have any questions or want to be put in touch with someone on the MainStreet team, just reply and Nick will set you up with a personalized onboarding.

Links and Listens

For most of Not Boring’s life (it was called Per My Last Email then), the email was mostly links to things I was reading, listening to, and watching. I finally have some space in an email today, so I’m throwing back to PMLE and hitting you with links.

🚙 Self Driving Cars and the Future of Retail | Adrienne Alyzee

Adrienne was in the Write of Passage Fellowship with me. Her piece on how self-driving will transform retail is the most up Not Boring’s alley of any of them. Adrienne is a PM at Tesla, so she has a front-row seat to the future of self-driving, and while the first-order effects are well-covered, this is the deepest dive into the second- and third-order effects of autonomous vehicles.

🐜 Ant Financial

A bunch of people have asked if I plan on writing up Ant Group given that the Alibaba spinoff is massive, competitive with Tencent, and about to go public. I will one day, but maybe not before the IPO, so here are some of the best write-ups, courtesy of Patrick O’Shaughnessy’s thread (a few of which are written by Not Boring readers!):

If you make it through all six and still want me to write it up, let me know!

📈 S-1 Bonanza

Speaking of companies going public… Mario Gabriele’s S-1 Club has been on 🔥 writing about the wave of tech companies going public.

📕The Almanack of Naval Ravikant| Eric Jorgenson

Liking and quoting @naval on twitter is a meme at this point, but there’s a reason things become memes. Naval Ravikant, the co-founder and Chairman of AngelList, is a well of wisdom, one of the most prolific early stage investors on the planet, and his company, AngelList, is a sleeping giant (I’m going to write about this soon).

My friend Eric Jorgenson created a Naval-approved, Tim Ferriss-forwarded “Navalmanack” of Naval’s best insights from a decade worth of tweets, podcasts, and essays, and the whole thing is free on the site (or available to purchase on Amazon).

🎧🎮 Epic Games | Acquired Podcast

If you liked my Tencentessays, you’ll love this Acquired episode on Tencent’s most fascinating and Metaverse-ushering portfolio company, Epic Games. I don’t think I’ve missed a single Acquired episode; they’re source material for so much of what I write.

I would love to hear what you think about the sponsored post format. Let me know in the comments or by replying to the email. I’m going to keep experimenting, and your feedback will help me get it right.

Thanks for listening, and see you on Monday!


Not Boring by Packy McCormick
Not Boring by Packy McCormick
Business strategy, but not boring, delivered to your ears and your inbox every Monday and Thursday morning.