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Matthew Gira

Build your bootstrapped business to $250k in revenue. Each week, I share tactics and strategies of how founders build sustainable ventures without venture capital

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Featured Post

Lessons learned from shutting down a startup

Hi friend! This week's video is one that I took some creative risks with and is one that is pretty personal to me. I went back to the place where I launched my last startup and talked all about the experience of what it's like to shut down a company. Curious to hear what you all think of this one. What's a hurdle you're struggling to get over with your startup? Happy to help if I can. Just reply to this email :) Here's this week's video: 5 years ago, I was shutting down the startup I...

6 months ago • 3 min read

Hi friend! I'm traveling this week and have a pretty unique interview lined up while I'm traveling. Excited to eventually share this one 👀 In the meantime, I joined the exodus off of X/Twitter and am on Threads! Let me know if you're on there too. What's one hurdle you're trying to get over with your business? Happy to try to help if I can! Now, here's this week's deep dive: Here's this week's deep dive: “I’m probably more stable” was Asia Orangio’s response to when I asked her “why start...

1 day ago • 1 min read
A YouTube thumbnail featuring a social media post-style text overlay reading 'I quit referrals completely' with the name 'Kendall Cherry' and a verified checkmark. The main image shows a person in a cozy red sweater and jeans sitting casually on a white d

Hi friend! I don't know about you, but this past week has felt like an entire month. So much going on. Thankfully, I was able to re-focus by the end of last week and create a new deep dive that was a lot of fun to create. Also, how about them Detroit Lions?!? #JaredGoff Now, here's this week's deep dive: Here's this week's deep dive: Most founders who have built a services business will tell you referrals are the lifeblood of their business. But Kendall Cherry believes referrals are actually...

9 days ago • 1 min read
YouTube thumbnail for 'How Tally Reached 11K Users in One Year' featuring a profile Twitter/X-style card against a background of minimalist form interface illustrations. The card contains Marie Martens' profile picture, name, and verified checkmark, with

Hi friend! Happy Election Day! I'm not sure about you, but I've planned a full day so I don't just watch the news all day and lose my marbles 😂 Besides the election, many things feel like they're in the works! Excited to share them in the next few months. In the meantime, here's this week's deep dive: What's one growth strategy you're curious about?? Here's this week's deep dive: Two founders launching a travel startup at the beginning of a global pandemic and somehow that leads them to...

16 days ago • 1 min read
A split image showing Jermale Eddie, a Black entrepreneur in a black suit and gold tie, smiling confidently against a backdrop of colorful fresh fruits and produce. Above him is a social media-style text bubble with his name and verified checkmark, and th

Hi friend! I was at FinCon most of last week and met a lot of wonderful founders. Always cool to see everyone in person rather than on Zoom. This week's deep dive is one I was able to see happen a little bit as I was working around the corner from this one for about a year. It's also a little different as this business went to $250k in revenue in 2.5 years, but is now shut down. More on that in the deep dive. What's one growth strategy you're curious about?? Here's this week's deep dive:...

23 days ago • 1 min read
The image shows a composite design featuring a social media post and a photograph of a woman, set against a futuristic background with green and blue digital elements. On the left is a mock social media post with a profile picture, the name "MaryBeth Mask

Hi friend! It's officially hoodie weather here in the Northeast and I couldn't be more excited. Be prepared to only see me in hoodies for the next 6 months in videos. Sorry not sorry. This week's deep dive was a fun one. Proof that you can build a solid side hustle and then transition that to a full-time gig :) Now, on to this week's deep dive. What's one growth strategy you're curious about?? Here's this week's deep dive: "You have no business being employed.” That’s what MaryBeth Maskovas’...

about 1 month ago • 1 min read
Thumbnail image showing a smiling man with short brown hair and beard, wearing a black t-shirt. A social media post overlay features a profile picture and the name 'Nathan Barry' with a verified checkmark. The post asks 'Did you write 1,000 words today?'

Hi friend! This week's deep dive is from June, but there are some updates! If you don't know Nathan Barry and Kit, check out this week's deep dive. Nathan has a fantastic story and is leading the way in building a scalable software company entirely bootstrapped. Now, on to this week's deep dive. Here's this week's deep dive: Today, Nathan Barry is the CEO and founder of Kit. Kit helps creators who mean business and is primarily an email newsletter tool for creators. Today, Kit makes over $40...

about 1 month ago • 1 min read
The image shows a social media-style post with a profile picture and name "Eduardo Placer" with a blue verification checkmark. The post text reads "If you can clean toilets...". To the right is a larger image of a smiling man with a bald head and beard, w

Hi friend! I tried something new with this week's deep dive. I didn't write while I was recording the video, I wrote on top of the video after I recorded it. I'd love your feedback on it. Better or worse than writing during the video?? Now, on to this week's deep dive. If I can be helpful to your business in any way, reply to this email! Happy to give feedback or be a brainstorming partner! Here's this week's deep dive: Artists often find it challenging to build businesses, as trading their...

about 2 months ago • 1 min read
Image of Amy Porterfield, a successful online business strategist, smiling while wearing a bright yellow blazer. Behind her is a modern office setup with plants, shelves, and a desk. A quote overlay reads: 'Amy Porterfield: You need a 10% edge.

Hi friend! This week's deep dive was a little more research than I was originally expecting 😅 I didn't interview the founder this time, but used other's interviews and her own posts to do this deep dive. I learned a lot about my workflows and how webinars can actually work?!? Now, on to this week's deep dive. If I can be helpful to your business in any way, reply to this email! Happy to give feedback or be a brainstorming partner! Here's this week's deep dive: Porterfield has become the queen...

about 2 months ago • 1 min read
Two men sitting on minimalist white tables in an industrial space. On the right, a Twitter-style post by Ben Young with a verified checkmark says 'We turned 3 tables into 100'

Hi friend! Who knew putting together a new studio and office setup was so much work?? No new videos from the new studio yet, but next week should be from there 👀 This week's deep dive was more personal for me as I met this team within a year of them starting. It's so cool to see people you've worked with a bit take their venture to some impressive places. Now, on to this week's deep dive. Here's this week's deep dive: It sometimes takes a few swings to craft the right product to meet market...

2 months ago • 1 min read
Erin Rollenhagen in a white suit on the left, with a text bubble to the right of her saying "All of your business comes from ___________". The background is cornfields but with a city in the background to show where Erin built Entrepreneurial Technologies

Hi friend! This week is a busy one for me. One of my largest events is on Thursday, and I'm moving to a new place this weekend. I'm excited about all of it, though. The move will help with these deep dives since I'll be closer to NYC, and it'll be a new studio setup for the videos 👀 Now, on to this week's deep dive. Here's this week's deep dive: In 2007, everyone was naïve about what would happen to the economy. Erin Rollenhagen was no exception—she was equally unaware of the economic turmoil...

3 months ago • 1 min read