Tag Archives: Software

Why I Just Invested in Rilla, the Killer App for Outside Sales

Every day, sales reps go to meetings across America to land that big deal.


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Their managers hope they absorbed the lessons of training and can bring in the sale. Unfortunately, they rarely have the time to go along.

But with cutting edge AI, sales managers can now analyze every customer meeting without ever leaving their office!

Rilla records sales meetings and tags the most important moments. You’ll know if reps are following the script, what customer objections are, and a lot more.

Other platforms like Gong or Chorus may work for inside sales with its clean audio. But for outside sales in the noisy, chaotic world, Rilla is king.

You just press record on a phone or tablet and that’s it! Rilla takes care of everything else.

No wonder sales teams are adopting Rilla at an incredible rate.

Sales managers see a 20-30x productivity increase. Reps get the feedback to make their pitch better than ever, meaning more commissions.

I’m delighted to be an investor in Rilla’s recent seed round. The founder, Sebastian Jimenez, is tenacious and laser-focused on his customers.

If you’re in outside sales, book a demo with Rilla and see what it can do for you!

More on tech:

Seeing Through SBF: How One VC Found the Truth

Getting to $10 Million ARR Without a Series A

Why I Love B2B Startups

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Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Misfits Market

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $15 on your first order. 

Photo: Sebastián Jiménez, Founder & CEO of Rilla

Why I Just Invested in ProsperStack

You work hard to get new customers. So why let them slip away?

ProsperStack lets you provide custom offers when a customer tries to cancel. They can even segment your customers and give the best offers to your top customers.


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You can also A/B test different offers to see what works best. And you can do all this in a beautiful, no-code interface!

Only the largest companies, like Netflix, have special programs to stop churn. But why shouldn’t your company have it, even if you’re not a giant?

ProsperStack can also help you understand why customers leave. They can tell you “you lost $10,000 in monthly recurring revenue because you don’t have a Salesforce integration.”

That gives your company amazing direction. It’s time to put that Salesforce integration at the top of the list!

But the thing I like most about ProsperStack is that you can easily see how much revenue ProsperStack stopped from churning. This makes their value proposition crystal clear.

I’m delighted to be an investor in ProsperStack’s recent seed round! Book yourself a demo and crush your churn today!

What issues do you see with subscription churn? Leave a comment at the bottom and let me know!

There will be no blog on Monday. I have an acting gig!

See you on Tuesday. Have a great weekend, everyone! 👋

More on tech:

Q3 Venture Funding Slows to a Crawl

The Startup Red Flags

You’re Doing Investor Meetings Wrong

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Misfits Market

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $15 on your first order. 

Midas Speaks: Sequoia’s Don Valentine at Stanford GSB

“We love recessions. Best time to invest in our experience.”

That’s Don Valentine, founder of Sequoia Capital and perhaps the greatest VC of all time. Today, I dug into a fascinating talk he gave in 2010 at the Stanford Graduate School of Business (GSB).


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Valentine breaks down Sequoia’s investment approach, which heavily emphasizes markets.

Sequoia only wants to bet on companies taking on the biggest markets. If the startup isn’t solving a huge problem, the odds of an outlier success are slim.

“If you don’t attack a big market, it’s highly unlikely you’re ever going to build a big company.”

Don Valentine

Valentine is wise to emphasize the size of the opportunity. After all, a tiny number of highly successful startups drive almost all the returns in venture capital.

I’m going to focus more on market size, based on Valentine’s advice.

An outstanding founder with a rapidly growing company is great. But if she doesn’t have a giant market to grow into, the company can only go so far.

Once Valentine finds a market he likes, he often makes numerous investments in that area.

He invested in Apple, which helped create the PC market. Then he invested in other companies to produce memory for the PC’s, peripherals, etc.

Presciently, Valentine mentions the opportunities in the mobile market in his talk. This was in 2010, just 3 years after the launch of the first iPhone.

Sure enough, Sequoia made a killing betting on the iPhone ecosystem. The firm invested early in Instagram, WhatsApp and others, netting billions.

At one point, Valentine shows a slide of some of the greatest founders he’s invested in.

What strikes me is how happy many of them look. They’re beaming, ear to ear.

This is the look of people who are building what they dream of and reaching their full potential.

Now, I’m off to find some entrepreneurs like that!

More on tech:

Managing a Crisis the Sequoia Way

John Doerr’s Biggest Mistake

The Power Law (Part One)

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Misfits Market

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $15 on your first order. 

The Top 5 Things I’ve Learned from Angel Investing

Some day, I want to look up at a big billboard in Times Square and say, “I knew that company when it was three people. And I saw what it could be.”

But how do I get there?


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I’ve been investing in early stage startups for 15 months today. I went from knowing absolutely nothing about the field to a portfolio of 13 companies.

Here are my top lessons so far:

1) Pay close attention to margins and scalability. Pure software businesses can scale easily.

For businesses that sell physical products, it’s much harder. It’s tough to sell 10 times as many physical goods as you did last year.

In today’s supply chain hell, it may be hard to even find the goods!

But strong software businesses can grow at warp speed. It’s no wonder that all the biggest winners in startupland are pure software businesses.

2) Build relationships with top investors. I don’t know for sure who will find the next billion dollar business.

But I have a pretty good guess of who it might be: someone who has found one before!

Build relationships and co-invest with investors whose track record is strong. They have the great dealflow you need.

3) Look at lots of deals. I look at 100-200 deals a month.

I choose one.

Look at lots of deals from top investors. This will give you a good idea of what the best companies in the market are right now.

Those are the companies you want to be in.

4) Help founders. This not only helps your existing investments, it builds your reputation in the industry.

The stronger your reputation is, the more good deals will come your way. Plus it’s fun!

What each investor has to offer is different.

I’m best at finding new investors for startups. But other angels might excel at marketing advice, product design or something else.

5) Always keep learning. More than anything, I learn by looking at deals and making investments.

There’s no substitute for actually doing deals, even if you make a few mistakes.

Consider them tuition! It’s a lot cheaper than business school.

I also talk to smart people, read books, and listen to podcasts that teach me more about the industry.

There’s always more to know, and it’s always changing!

Here are some great resources:

Angel by Jason Calacanis

This Week in Startups Podcast

The Power Law by Sebastian Mallaby

Venture Deals by Brad Feld and Jason Mendelson

Bottom Up by David Sacks

Lenny’s Newsletter

This is a field that can be learned. Dig in, find great information, and learn from experience!

If you’re interested in technology and business, you’ll find it very rewarding! You have a small hand in helping create the future.

What questions do you have about angel investing? And how can I improve my process?

Leave a comment at the bottom and let me know!

More on tech:

The Power Law (Part One)

Talking Startups and Today’s Fundraising Pullback

How to Write Investor Updates

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Misfits Market

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $15 on your first order.

Photo: “If God Will Send His Angels” by just.Luc is licensed under CC BY-NC-SA 2.0.

What the Best Founders I Know Have in Common

Hi everyone, hope you had an awesome weekend! Today, I want to talk to you about some of the smartest people I know.

As an angel investor, I meet with a lot of startup founders. As I took a walk on the Hudson today, it occurred to me that the most successful ones all remind me of each other.

So what distinguishes the best founders from the rest? Here are a few thoughts:

1) They have all the facts at their fingertips. Whenever I ask them a question, they tend to know the answer cold.

I could be asking about a product feature, customer acquisition strategy, or a metric like gross margin. Whatever it is, they’ve thought about it already and know all the relevant facts.

2) Strong customer focus. The most successful founders I’ve seen are obsessed with their customers.

They know everything about them and what they need. And they tailor their product ever more carefully to those needs as time goes on.

What are the less successful founders focused on? Often their competitors, someone “stealing their idea,” or endless fundraising.


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We should always remember that the business’s goal is to serve the customer. Don’t let distractions take you away from that.

3) Openness to questions and criticism.

The best founders I’ve seen gladly answer any question an investor asks. They’re eager to show off their awesome product and happy customers!

The less successful ones evade questions and try to convince investors the business is going better than it really is. I sometimes suspect they’ve convinced themselves too, at their peril.

If we’re forthcoming with information and open to constructive criticism, we can learn from others and improve!

One of the most exciting moments for me as an investor is when a new founder reminds me of one of the best I’ve met. That’s when I start to salivate and reach for my checkbook. 🙂

The good news is that the best founders have a lot to teach all of us about how to up our game, if only we’re willing to listen!

What do you think makes a great founder? What did I miss?

Leave a comment at the bottom and let me know!

More on tech:

The Startup Pitch Checklist

Amp It Up

How to Write a Deal Memo

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Photo: “A Street Called Awesome” by moonlightbulb is marked with CC BY 2.0.

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

Misfits Market

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $15 on your first order. 

Judging a Startup Pitch Competition

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Last night, I had the honor of judging a startup pitch competition. Each founder in the Starta Accelerator in NYC had 3 minutes to pitch a panel of judges in front of a live audience.

I was so impressed with the hard work these entrepreneurs are putting into building their companies and pitching investors!

I also came away with some insights that might help other founders. Maybe you!

1) Be sure I know what your company does within the first minute.

Some founders do an amazing job of summarizing a problem, but aren’t as clear on how they’re solving it. The most important thing you can convey in your pitch is what your company does.

Don’t bury the lead!

2) Tell us exactly how you make money. Some founders do a great job of explaining what their product does, but don’t tell us how they actually get paid.

One of the key things investors are trying to learn about your company is the revenue model. So make it a big part of your pitch.

3) Clearly state the terms you’re raising at. After watching 6 companies present, I noticed they all had one thing in common: not one said what valuation they’re raising funds at!

Tell us how much you’re seeking to raise and at what valuation. And be clear as to whether the valuation is pre-money or post-money.

You also want to mention how much money is already committed to the round, if any.

Here’s a good example sentence: “We are raising a $1 million seed round on a $7 million pre-money valuation with $500,000 committed.”

Some founders are reluctant to ask for anything out of modesty. Others don’t want to be pinned down to a particular valuation because they want to negotiate it later.

But you must ask investors for something specific. Otherwise, what’s the point of your presentation?

You can always negotiate those terms later, but be sure to offer a starting point.

4) Give us some key numbers.

We investors love metrics. So show us your month-over-month revenue growth rate, gross margin, churn rate, net revenue retention, etc.

A good story is essential, but good metrics close the deal.

And finally, on a hopeful note…

5) You can improve your pitch enormously in a short period of time, if you do the work.

I saw one of the founders that pitched last night two weeks ago. In that early pitch, I honestly had no idea what the company did.

When I saw him last night, he was polished and crisp. I knew exactly what his company did and why.

And I almost found myself reaching for my wallet. 😄

If you put the work in, you can improve. Repetition goes a long way!

What do you think makes a great pitch? And what questions do you have for me about speaking to investors?

Leave a comment at the bottom and let me know.

Have a wonderful weekend everyone! 👋

More on tech:

How Startups Can Dominate the Elevator Pitch

Why Your Startup Shouldn’t Be an LLC

Find Code Faster Than Ever

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Photo: “JudgeThumbUp” by cali.org is marked with CC BY-NC-SA 2.0.

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

Find Code Faster Than Ever

I have something really cool to share with you guys before you head off for the weekend!🕺🎉

An amazing new tool called Snipt.dev launched yesterday. It makes searching for code to re-use easier than ever.

Snipt.dev is a project by Codiga, an awesome “Grammarly for code” tool in which I’m an investor.

I briefly introduced you to Snipt.dev yesterday, but today I’m turning the blog over to creator Julien Delenge to explain what makes this tool so special:

Snipt: Search Engine for Code Snippets

We are excited to announce the release of snipt.dev, a search engine to help engineers find safe and reliable code patterns. Code Snippets are very popular for developers but the ecosystem of tools is very fragmented and not unified. Developers are often looking for snippets to use and spend hours searching on Google, StackOverflow or Sourcegraph.

To help developers find the right code snippet, we built snipt.dev: a one-stop shop for searching for code you can reuse.

But first, what is a Code Snippet?

Code Snippet is a block of code you can share and reuse. By reusing safe and proven code, you not only improve your productivity but you also make sure you always import the correct code and are not missing anything (e.g. missing argument, not checking error code or exceptions).

By using rock-solid, proven code, you avoid many common pitfalls and mistakes developers already did. You find the correct block of code to reuse to focus on what matters: shipping code and improving a product.

Why use Code Snippets?

Writing code is quite complex and requires having a really good knowledge of the language and libraries you are using. Even with languages with lots of abstractions, it is often hard to follow the code path and understand how code actually works! Sharing and using vetted code patterns directly in your IDE maximizes your productivity but also make sure you are using the correct code block for your job!

So now, what is snipt.dev?

snipt.dev is a new platform for searching code snippets. It includes a semantic analysis feature that detects what framework, library, or language you are looking for and optimizes the search results based on your criteria. For example, if you look for “react typescript”, the engine will only show snippets related to TypeScript while “react javascript” will show you only snippets related to JavaScript (and obviously, react).

snipt.dev is built to be blazing fast: a request takes just a few milliseconds to come back to you. As with most search engines, results are suggested as you type, showing you the most relevant snippets for your query.

Adding your own snippets

The engine indexes and searches snippets from the Codiga platform. To add your own snippet to snipt.dev, simply add snippets on the Codiga platform: they will be automatically indexed and visible on snipt.dev. Adding snippets is very easy and can be done directly from your IDE using Codiga plugin (see VS CodeJetBrains, or Chrome plugins). You can find more information in the Contribute section of snipt.dev

Open-Source

snipt.dev has been designed using popular open-source libraries (NextJs, GraphQL) and it was natural for us to share this project with the community. You can find this project on GitHub. If you have any comments or issues to report, please open an issue on the GitHub project.

Pretty cool, eh? Have a great weekend everyone! 👋

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

Awesome New Code Search Tool Launched Today!

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Hey guys! 👋

I don’t usually do 2 posts in a day, but this is too cool not to share with you right away!

Just this morning, an amazing new search engine for code snippets launched on Product Hunt!

It’s called Snipt.dev.

Rather than endless searches on Stackoverflow or Google, you can quickly find the code you need and get back to building.

This is a project of Codiga, an incredible startup I’m an investor in. It’s basically Grammarly for code and can substantially improve your productivity.

I plan to have a lot more information on this awesome tool here for you tomorrow, but until then, give Snipt.dev a try and save yourself some valuable time!

More on tech:

Codiga: Grammarly for Code

The True Story Behind WeCrashed

How to Ace a 3 Minute Pitch

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

The Lean Startup

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“There is surely nothing quite so useless as doing with great efficiency what should not be done at all.”

Peter Drucker

You’ve written a 92 page business plan. For three years, you hunched over your laptop coding, sustained by Red Bull and Cheetos

At last, launch day is here! You press the button and…

Nothing happens.

You keep refreshing the page, but no one is signing up. You try one marketing channel after another, convinced that massive growth is right around the corner.

But the hard truth is, no one wants what you’ve built.

That is a hard moment for anyone. And it’s why Eric Ries wrote the seminal book The Lean Startup, which I just finished this morning.

The Lean Startup framework involves creating a Minimum Viable Product (MVP) and getting it to customers ASAP. Then, by seeing how customers use it, you make changes to the product (“iterate”) to see if you can serve customers better.

Build-Measure-Learn is the loop you want to go through as frequently as you can. Build something you think customers need, measure how it does with customers, and learn how to do a better job meeting those needs in your next version.

“The question is not ‘Can this product be built?’ In the modern economy, almost any product that can be imagined can be built. The more pertinent questions are ‘Should this product be built?’ and ‘Can we build a sustainable business around this set of products and services?’”

Eric Ries

Ries gives some incredible examples of just how minimal that MVP can be.

Nick Swinmurn started Zappos by taking pictures of shoes in nearby stores. He put those pictures on his website and if anyone ordered a pair, he went to the store, bought and shipped them.

“But that doesn’t scale!”

Sure it doesn’t! But in 1999 when Swinmurn founded the company, no one knew if people would buy shoes on the internet.

Starting with a mostly manual process was a lot better than Swinmurn spending months if not years and untold sums building infrastructure to accomplish what no one wanted in the first place.

Early stage startups have limited capital and only so much time to prove their business can work. By getting through as many cycles of Build-Measure-Learn as possible, founders give themselves the best chance at finding a viable business before the clock runs out.

In just 11 years, Ries’ ideas have gone from unusual to being the accepted way to run a startup. His book, while at times a slog, is essential reading for both founders and investors.

I’ll leave you with the quote that struck me most. It’s one I aim to live by:

““…if you cannot fail, you cannot learn.”

Eric Ries

More on tech:

The High Growth Handbook: Scaling Startups from 10 to 10,000 People

How Startups Can Dominate the Elevator Pitch

What I Look For in Startups

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Photo: “Eric Ries – The Lean Startup, London Edition” by betsyweber is marked with CC BY 2.0.

If you found this post interesting, please share it on Twitter/Reddit/etc. This helps more people find the blog! 

Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order. 

Fathom: the Podcast Player from the Future

Let’s say I have a question: “how do angel investors choose startups?” I go to Google and type it in, right? 

But what if the best answer is in a podcast? That audio is trapped somewhere in the dark world of RSS feeds, along with great answers to millions of other questions.

Until now! Fathom makes it easy to search podcasts. 

Let’s try my search on Apple Podcasts:

Bupkus. Now let’s try it on Fathom:

Right away, Fathom directs me to a highly relevant clip from This Week in Startups, a podcast I love! Jason advises me to diversify my investments and make sure I’m choosing companies with products in market.

Sage advice. Question answered.

Do you see how powerful this is? Tons of smart people are talking on podcasts every day, but unlike text, that info is almost impossible to search.

Fathom grew out of a side project during the COVID lockdown. Here’s co-founder Paul Bloch:

Ken, my cofounder reached out to me and mentioned that during the covid lockdown he’d been working on a prototype AI that could answer questions using podcast content. Ken’s a podcast lover and big Lex Fridman Podcast fan. Ken asked if I wanted to help develop the idea and product with him. 

After we started in earnest we felt that there were many more ways we could bring the power of AI to the user and innovate in how people experience podcasts. That’s what brought about the feed of AI-recommended episodes that play AI-generated highlights. 

…I believe in January of 2021 Lex Fridman had an interview where he specifically mentions how game-changing it would be to search inside podcasts. That was the moment of kismet that really made us excited about the potential of the product. Months later we had a prototype, incorporated the company, and had our first investor check. Things started moving fast the moment we really committed to bringing our vision to life.

The application is available on desktop or iOS. As a podcast maniac, I’m really excited to be an investor in this great company!

Give Fathom a try and have fun listening to some awesome episodes! 

More on tech:

Vade: The Future of Parking

Founders’ Biggest Pitch Mistake

Male Contraception With an Ultrasound Device?

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Save Money on Stuff I Use:

Fundrise

This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been great so far.

More on Fundrise in this post.

If you decide to invest in Fundrise, you can use this link to get your management fees waived for 90 days

Misfits Market

My wife and I have gotten organic produce shipped to our house by Misfits for over a year. It’s never once disappointed me.

Every fruit and vegetable is super fresh and packed with flavor.

I thought radishes were cold, tasteless little lumps at salad bars until I tried theirs! They’re peppery, colorful and crunchy!

I wrote a detailed review of Misfits here.

Use this link to sign up and you’ll save $10 on your first order.