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Bootstrapped Web is for entrepreneurs who are bootstrapping web startups and believe in order to achieve success, we must learn by doing. Interviews with bootstrapped entrepreneurs and case studies in building profitable businesses.
 
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
 
Welcome to Bootstrapped Growth where you will get actionable, tactical steps you can implement immediately to get results. No latest tips or tactics. No mindset training or feelings. Myself and the guests I bring on are going to share with you the most effective sales, marketing and business skills, strategies, and frameworks so you can repeatedly build a business in any economy.
 
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Dingman Bootstrapped

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Dingman Bootstrapped

The Dingman Center for Entrepreneurship at the Robert H. Smith School of Bu

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The Dingman Center for Entrepreneurship at the Robert H. Smith School of Business produces Bootstrapped, a podcast featuring founders, investors and serial entrepreneurs. While the podcast covers many aspects of startup life, the heart of the show focuses on funding from both the founder and investor perspectives, thus the name Bootstrapped. The podcast is hosted by Elana Fine, Managing Director of the Dingman Center, and Joe Bailey, Associate Research Professor at the Smith School. Each epi ...
 
Backstage Capital is venture investment fund that backs underrepresented tech startup founders. Since inception in September 2015, Backstage has deployed nearly $2m into 40+ startups around the U.S. that are led by women, POC, and LGBT founders. This podcast takes you behind the scenes to show you what it's like to build a fund from scratch and give you deep insights into what investors are REALLY looking for. You'll laugh. You'll cry. You might steal a donut. But that'll have nothing to do ...
 
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show series
 
Mike Kaeding is the CEO of Norhart. Norhart designs, builds, and rents apartments. They are transforming the way this is done by incorporating technologies and techniques that have revolutionized other industries. This has resulted in improved quality and reduced cost of housing. They are currently constructing beautiful properties for 20-30% less …
 
JB Jezequel, a co-founder of Evaboot and a lead generation expert, appears on this episode of The Bootstrapped Mafia Podcast. JB bootstrapped his B2B SaaS business from $0 to $1M ARR in the last three years while being the sole person in charge of client acquisition.💰 Evaboot is a scraper, a Chrome Extension that helps to extract clean data and fin…
 
To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain val…
 
Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in ZipMessage – Jordan’s hiring an SDR – Learning from strategic decisions that went wrong – Product insights with vs without a product in market Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for …
 
Kyler Nixon is the founder of Kyler Creative Marketing Agency. He is on a mission to help 1,000 brands each earn $1,000,000 through courses and memberships in the next 10 years. https://www.linkedin.com/in/kylernixon/ https://twitter.com/Kyler_Nixon Kylercreative.com/newsletter Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjoh…
 
Back for our weekly founder therapy session, err… podcast episode Here’s what’s up this week: – Brian (finally) ships sub-threads in ZipMessage – Jordan’s hiring an SDR – Learning from strategic decisions that went wrong – Product insights with vs without a product in market Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for …
 
Today, I’m talking to Laura Elizabeth. She co-hosts the Non-Tech Founders podcast and runs several products as a non-technical founder. We talk about outsourcing, trust, and building an audience around your business. Here’s Laura! 00:00:00 Laura Elizabeth 00:02:10 Running a non-technical founder podcast 00:09:28 Hiring the right people 00:12:14 Hir…
 
Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebies: https://www.podseam.com/freebook How to Submit Your Podcast to IMDB.com Podcast Growth Checklist Creator Marking Platforms 99+ Awards Worthy of Winning Creator Hub…
 
This episode of The Bootstrapped Mafia Podcast features Sai Krishna, a founder with a unique perspective on product validation and success indicators. I very much enjoyed hearing his thoughts on determining the best product to build and building in public. For the past 11 years, Sai has been indiehacking and launching startups. He had millions of u…
 
Carlos Henry is a performance coach for young minority entrepreneurial men to teach them how to achieve their goals in one year where it takes most 3-4 through some of the most powerful high income skills. www.carlosjhenry.weebly.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podca…
 
In this episode of The Bootstrapped Mafia Podcast, I spoke with Fed. Folio is a bootstrapped founder, digital nomad, and creator of The Hive Index and GummySearch. Every month, The Hive Index assists over 10,000 people in finding online communities, and GummySearch generated $60,000 in revenue in its first year. GummySearch is an audience research …
 
To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain val…
 
Link Moser has been working for himself since he was 12 years old, mostly doing freelance web design and some real estate sales on the side. https://www.linkedin.com/in/linkmoser/ https://twitter.com/linkm https://www.linkmoser.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast…
 
We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ecom becoming “a thing” – ChatGPT is firmly in Brian’s coding workflow Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.…
 
We kick off 2023 with a grab bag of topics: – Jordan’s building in public more – Brian’s building solo with contractors – Headless ecom becoming “a thing” – ChatGPT is firmly in Brian’s coding workflow Brian on Twitter Jordan on Twitter ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.…
 
Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures. 00:00:00 Daniel Fayle 00:05:35 Getting started with Chekkit 00:09:00 Lo…
 
Daniel Martinez is a Saas founder and real estate investor. https://www.linkedin.com/in/danielhivemind/ https://twitter.com/danielhivemind https://hivemindcrm.io/ Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebies: https://www.podseam.com…
 
I spoke with Dagobert Renouf, Co-Founder of Logology, on this episode of The Bootstrapped Mafia Podcast. Dagobert founded Logology in 2018 as a side project with his wife. They wanted to start a business that would allow them to use both of their talents and make them happy to come to work every day. They decided to build an online tool in the desi…
 
Rob is a lifelong problem solver and software developer that loves to help others be their best. https://linkedin.com/robbroadhead https://twitter.com/develpreneur https://develpreneur.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebie…
 
I was chatting with Marissa Goldberg about remote work this week, and she gave me several handy frameworks for founders who want to build remote-first businesses. At the center of any successful remote work relationship lies trust. And surprisingly, many businesses have a tough time trusting anyone once they can't see them at their desk in the offi…
 
Steve specializes in helping small online businesses set up the foundation so they can eventually 'exit' their existing business. https://www.linkedin.com/in/stevekilberg-e-commerce-coaching-mentor/ https://skrpmedia.com/ Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://…
 
Today, I’m talking to Marissa Goldberg. She’s an expert in remote work and guides companies and founders alike toward a future-proof workplace. We’ll talk about productivity, best practices for going remote, and setting up a remote team of all sizes. Here’s Marissa. 00:00:00 Remote Work and Future Proof Workplaces 00:02:03 What is Remote Work Prep?…
 
Cora Kessler is the founder of Small Magic Studios, a digital marketing consultancy that helps small to mid-sized business to get unstuck. https://www.linkedin.com/in/cora-kessler-37787148/ https://www.smallmagicstudios.com/ Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https…
 
This week I chatted with Patrick Campbell about his exit of ProfitWell to Paddle for $200 million. One of the most mind-blowing things that I experienced during that conversation was hearing Patrick tell me that he feels he needs to build something else to prove that his exit -$200 million- was not just a fluke. I did not expect that, but I should …
 
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking with us another year on Bootstrapped Web. “Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This Plugin Tweet This Talking Points: Viruses, holiday cards, and coming …
 
We look back on the ups and downs in 2022 and look ahead to 2023. The emotional rollercoaster rolls on… Thanks for listening and for sticking with us another year on Bootstrapped Web. “Everything before product-market fit is a form of suffering” – Jordan Powered By the Tweet This Plugin Tweet This Talking Points: Viruses, holiday cards, and coming …
 
Today, I’m talking to Patrick Campbell, founder of ProfitWell, a bootstrapped business that recently got acquired by Paddle for a whopping 200 million dollars. I talked to Patrick about getting acquired for 9 figures, finding your footing as a founder after such an incredible exit, where the online payment industry is heading, and how mental health…
 
As a creative entrepreneur, it is important to diversify your portfolio and have multiple projects in progress in order to reach a wider audience, stabilize income streams, and protect yourself from the risks associated with relying on any one platform. In order to do this, it is essential to own the means of communication with your audience, such …
 
Today, I’m talking to Jay Clouse, a creative entrepreneur, and all-around amazing human being. We’re talking about keeping it all together as a solo creator, what makes a personal brand work, and how important authenticity is in building an audience. 00:00:00 What to do about all the attention-grabbing out there 00:05:00 A trust-based paradigm for …
 
Resources Mentioned: NuclearNetworking.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebies: https://www.podseam.com/freebook저자 Sarah St John
 
Sharing your work and process in public can be difficult for introverted entrepreneurs and creators, but it can help build credibility and trust with your audience, gather valuable feedback and insights, and even lead to new opportunities. Tips for sharing in public include reframing why you do it, taking it slow and steady, breaking it into small …
 
Today, I’m talking to Ana Bibikova, a defender and cheerleader for introverts in entrepreneurship. Ana knows what it means to be skeptical of loud and salesy marketing tactics. They might work great for extroverts, but not so much for the quiet types. Today, we’ll talk about how you can build a public-facing brand without resorting to all the obnox…
 
Yesterday, the creator economy learned that Gumroad, a platform where creators have been building their businesses by selling their services and products, increased their prices significantly. That caused a lot of backlash in the community, with people threatening to switch to other platforms and criticizing how the price hike was communicated. It’…
 
Resources Mentioned: StationRove.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebies: https://www.podseam.com/freebook저자 Sarah St John
 
When it comes to selling a small indie business, defensibility is a key factor that potential buyers will consider. A unique moat, or competitive advantage, lets your business stands out from the competition and is seen as a valuable acquisition. Many small founders sell their businesses because they want to get rid of them, and that attracts barga…
 
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “What can this do? How does th…
 
We asked ChatGPT to suggest some topics for today’s episode but it came up short. So you’ll have to settle for the boring human versions of Brian and Jordan, talking about what’s happening in ZipMessage and Rally. Enjoy. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “What can this do? How does th…
 
Today, I am talking to Andrew Gazdecki, a pillar of the founder community and himself founder of the acquisition platform formerly known as MicroAcquire — but we’ll learn more about that on the show. Besides organizing millions of dollars worth of acquisitions every month, Andrew is a true teacher. His content on building software businesses is spe…
 
Resources Mentioned: TheJumpstartKit.com TamiJaffe.com Follow the Frugalpreneur: https://www.frugal.show/ http://thesarahstjohn.com/podcast Get 1-on-1 Help With Your Podcast: https://www.podseam.com/ Get Your Freebies: https://www.podseam.com/freebook저자 Sarah St John
 
We've been taught to believe that creators are only truly successful when they reach the top echelon of their platform, with millions of followers and likes. But this is a false notion that doesn't accurately reflect what success looks like for creators — or what “success” is about in the first place. The truth is that success for creators comes in…
 
I am talking to Rosie Sherry, proprietor of Rosieland and community empowerment expert. She runs her own communities, monetizing a few of them, and has been managing the IndieHackers community in the past. Rosie is an expert all things community and education. And that's precisely what we'll talk about today. This episode is sponsored by MicroAcqui…
 
There is a huge difference between building a product, a business, and a company. It's a progression from one to the other, usually involving making significant changes in your life. Requirements change, and so does our lifestyle to make our dreams possible. Ideally, we have a master plan on how to get there. But in reality, we have to pay bills, t…
 
I'm the guest on my own podcast! A year ago, Ben Pages joined my company, Feature Upvote, to be our marketing manager. Ben had questions about the early days of Feature Upvote, and how this product came to be. He also wanted to know the origin of my low-stress approach to running a business. We thought, why keep this conversation to ourselves? Why …
 
Today, I am talking to Jakob Greenfeld. I’ve been reading Jakobs blog posts for years now, and they’re as spicy as they’re thoughtful. There’s not a single post on there that feels unfinished. That’s quite impressive. Well, I think we’ll figure out why that is during our conversation. We’ll also chat about how to unlock critical thinking by writing…
 
In my conversation with Daniel Vassallo this week, I learned that Daniel uses social media —Twitter in particular— to find inspiration for his own work as a teacher and content creator. Intentionally doomscrolling Twitter to come up with writing prompts and business ideas? Why not! If we consider this a strategic effort, not just wasting our time o…
 
Today, I am talking to Daniel Vassallo, writer, founder, and person with very strong opinions. He is building a portfolio of small bets in public, on Twitter. I will talk to him about the importance of making money in diversified ways, how to structure your life around being a founder, and how to figure out which business ideas might actually work.…
 
Dave Molenda, CPBA, CPDFA, CPEQA is the founder of Positive Polarity, LLC, a Midwest based coaching/training firm that brings solid growth to companies from over 30 years of real-world experience where he grew his business to $10,000,000.00 in annual sales before selling it. He speaks regularly at conferences around the country on topics that are d…
 
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