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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.
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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 ...
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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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What (and when) is a SaaS "feature complete"? How do we sell and negotiate mid-market contracts? How to please customers (and which ones are worth pleasing)? ...And other tricky questions we're thinking about this week. Connect with Brian and Jordan: Brian's company, Clarityflow Jordan's company, Rally Brian on Twitter: @casjam Jordan on Twitter: @…
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About the Guest: Travis Steffen has spent 14 years and millions of dollars building the playbook that's helped me start, scale and sell 8 companies. He's now helping other brilliant, passionate entrepreneurs trying to do the same thing. Relevant Links: StartupShortcuts.co Follow the Frugalpreneur: https://www.frugal.show/ Grab Your Free E-Books: ht…
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If you're an entrepreneur looking to start a digital business, you might be tempted to aim for a "forever business" right from the start. However, pursuing this approach can be dangerous. Today, you'll learn how to navigate the rapidly evolving landscape of digital entrepreneurship, build successful businesses that serve your customers and owners, …
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Aprilynne built up a YouTube channel from zero to over twenty two K subscribers last year. But she is starting all over again. No subscribers, no videos, no monetization, nothing. Her goal is to get Youtube monetised in 30 days. Will she make it? Let’s keep an eye. Key Takeaways [01:30] - Why skipping the Wall Street for a better life. [04:20] - Wh…
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In this episode of The Bootstrapped SaaS Operator, Geoff Roberts joins us with an inspiring story of Outseta. Tune in to learn more about: ~ How to stay determined even without any feasible results? ~ An interesting way to build an incredible team. ~ How to go against what is trending? Timestamps (00:00) - Intro (00:11) - What Problem Outseta Solve…
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In this episode, I interviewSimon Høiberg, an active software engineer, founder, and YouTuber. Simon shares his strategies for balancing his roles as a creator and maker, and discusses the importance of incorporating personal experience into his content. He also delves into the power of intrinsic motivation and joy in entrepreneurship, and how he g…
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About the Guest: Alex Sanfilippo is an entrepreneur and the founder of PodPros, a software company specifically focused on independent podcast hosts and their guests to elevate their voices through podcasting and be heard. Alex and the team at PodPros have developed popular podcasting software services such as PodMatch, PodcastSOP and PodLottery. I…
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Have you ever searched for the perfect resume to get hired? Or tried to create a product that appeals to everyone? This essay explores the logical fallacy of wishful reasoning and the importance of picking a niche. Discover why building a successful product means addressing a specific set of needs for a particular group of customers, and why a well…
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Evelyn J. Starr is a brand-building expert. We talk about finding the right niche, having a community-centric long-term perspective, and how brands evolve —you might call it “grow up”— over time. Here’s Evelyn. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm Evelyn's Twitter: https://twitter.com/EvelynJStarr The blog post: https…
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Building in public is a popular trend in entrepreneurship. However, it may not always be the best approach. Entrepreneurs should consider their personality traits, the nature of their business, and their competitive advantages before deciding whether to adopt this approach. Building in public is about generosity, transparency, and community, and ca…
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Pietro is a serial founder bootstrapping mobiloud.com, feedbear.com and mixbloom.com with a mind-blowing goal of moving from $1.5M to $5M ARR in 3 years. This is probably not for all indie hackers, but it is an amazing situation to be in. Key Takeaways [01:23] - A path from consulting to building digital products. [02:31] - "Go big or Go home" VS "…
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Today, I’m talking to Jack Ellis, the co-founder of Fathom Analytics, a privacy-conscious web analytics business that I personally use for all my web properties. The company that Jack co-founded with Paul Jarvis competes directly with Google on their linchpin advertising product. That’s a pretty high order. We chat about Jack's role in a growing su…
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In this episode of The Bootstrapped SaaS Operator, Lukas Hermann from stagetimer.io joins us. Stagetimer.io offers a countdown timer for the production houses, helping them manage time with an easy and simple yet effective tool. Tune in to learn more about: 1. How Lukas found a niche market? 2. How has buyer behavior affected Stagetimer’s pricing? …
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Brian and Jordan give their takes on the question of whether to start up your first business earlier vs. later in life. Plus: Board meeting takeaways, MRR growth, sales demos, enterprise vs. mid-market, and BBQ smokers. Brian's business: Clarityflow (formerly ZipMessage ) Jordan's business: Rally Follow us on the Twitters: @jordangal & @casjam…
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People would rather sift through fake AI results than see yet another ad. Something is happening in advertising, and the creator economy is affected greatly. The shift towards trust-based advertising is a wake-up call for founders and creators when crafting their marketing strategy, as honesty, integrity, and trust are now essential components of a…
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When Fatih started his sticker business Stikkernet, his peers asked him, “You’re a developer; why don’t you write this from scratch?” His response? “Why should I?” Today, I'm talking to my dear old friend Fatih Kadir Akın — or fka for short. We discuss his unexpected journey of building a successful business out of a simple idea. Fatih shares his e…
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Rox worked for MrBeast, Facebook, Microsoft, and other companies. Now, he helps big creators start software businesses while trying to live the most amazing life he can. He makes content about what he builds so you can follow it. Key Takeaways [01:12] - How to exit everything and bootstrap a SaaS product from Thailand. [03:26] - How to make money f…
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What happens when we encounter something so novel that our minds can't fully comprehend it? Today, let’s explore the "Rubber Band Effect" and how it impacts both journalists and entrepreneurs alike. Learn how to build products that fit seamlessly into your customers' workflows and how to effectively communicate the results your product can achieve,…
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“As an entrepreneur, you need someone you’ve been through shit with already” — and that’s exactly why Dagobert and Lucie are the perfect power couple co-founders. I chatted with @dagobertrenouf about overcoming struggle, growing a business together, and dealing with the lack of motivation when things get complicated. We discuss the power of Twitter…
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Using ChatGPT as a writing partner helps strengthen arguments by acting as an editor, proofreader, and devil's advocate. It prompts the AI to provide counterpoints and can detect emotional subtext, highlight missing pieces of the argument, and suggest better examples. This adversarial writing approach with generative AI results in writing that is b…
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Few people had an impact on my founder journey as Dr. Sherry Walling — and she didn't even know. But I got to tell her! We discussed burnout, imposter syndrome, and stress among founders. Sherry explained the need for mental health professionals who understand the unique challenges of entrepreneurship and shared that burnout is a diagnosable issue.…
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Jordan announces Rally's Series A and we unpack the whirlwind road that it took to get there. Brian launched a pricing increase, which coincided with a competitor's unexpected shut down. It's been a wild few weeks while we've been off, but we're back! Jordan's business, Rally Brian's business, Clarityflow (formerly ZipMessage )…
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This week, I got on my first post-COVID trip and headed to Denver, Colorado for MicroConf 2023. It. Was. Awesome. Unsurprisingly, being in the same room with 250 other bootstrapped SaaS founders is one of the nerdiest things you can do. And it was as enlightening as it was nerdy. I just arrived back home in Canada a few hours ago, so I took the opp…
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Previously, Jelani Abdus-Salaam was the lead VIP tech specialist at ClickFunnels, where he assisted Jay Abraham, Grant Gardone, Tony Robbins, and others. Following his time at ClickFunnels, he worked with high-profile digital entrepreneurs like Dan Lok, Alison Prince, Traffic and Funnels, Beau Crabill, and others, assisting them in developing conve…
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When it comes to building an "owned audience," nothing beats an email list. Louis Nicholls is a newsletter expert, and he shared with me how to monetize a list, how to grow it reliably, and why cold emails are often done spectacularly wrong. Louis will show you how to do email right. 00:00:00 Why did you choose to build SparkLoop? 00:05:23 Grow an …
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Resources Mentioned: Free Passive Income Workshop Free One Blog Away Course Blogger Evolution Empire Flippers Motion Invest FE International Ahrefs Archive.org Wordpress.org Share A Sale Commission Junction (CJ) ClickBank JVZoo Google Trends Follow the Frugalpreneur: https://www.frugal.show/ Grab Your Free E-Books: https://www.thepodplanet.com/free…
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ChatGPT is everywhere. But can we build businesses on it? What risks will we face? Let's dive into the future of entrepreneurship in a world where AI is ubiquitous. My new podcast project: Arvid & Tyler Catch Up / https://catchup.fm The blog post: https://thebootstrappedfounder.com/chatgpt-goldmine-or-minefield-for-indie-hackers/ The podcast episod…
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Zeno Rocha was a VP of Developer Experience at WorkOS at the time of our conversation, and he also had a handful of successful side projects, like the Dracula theme and React Email. React.email was created to assist developers in creating modern email templates. Zeno dug more and it became evident that this was only the top of the iceberg, since se…
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Marie and Ben are a power couple. Together, they run Notion Mastery, an intense workshop for people who want to use Notion professionally and productively. In our conversation, we'll dive into platform risk, building a sustainable educational business, how to work together as a couple, and why social media distribution matters a lot to educational …
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Artificial scarcity, a marketing tactic that fosters urgency in customers, can lead to short-term financial gains but raises ethical concerns and negative consequences in the creator economy. Drawbacks include damaging relationships, promoting impulsive purchases, and exacerbating global inequality. While there are exceptions, such as outcome-orien…
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Alex has sold his bootstrapped startup Taplio to another bootstrapped startup, Lemlist, since we recorded this episode - a big deal in the bootstrapped world. And it wasn't his first venture and entrepreneurship experience. In fact, he exited a few startups already. Alex is now working on Omni, which assists in the creation and implementation of an…
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Most of Josh Spector's newsletter issues are just a few sentences. Sometimes, just a link. And still, advertisers and readers alike flock to Josh's emails. In our conversation, you will learn why brevity is so attractive, how to make sure you're telling the right stories to the right people, and how to build systems that keep people coming back for…
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This is probably the most concentrated and well-produced podcast I've been on in a long while. And I want to share it with you here today as a bonus episode. Kudos to @YongSooChung for putting his money where his mic is. He spent a lot of time, money, and energy to make this episode happen. This is a great ep, and if want to learn about my whole fo…
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What are the factors involved in choosing a solid business name? From securing an available domain to choosing a unique name for SEO reasons, I delve into the linguistic and cultural considerations of choosing a business name, including avoiding potentially offensive or negative connotations in various markets. I also emphasize the importance of tr…
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Peter knows how to get good domains and turn them into businesses. He's selling onions, helps dude ranchers get clients, and will share his approach to monetizing domains as well as purchasing them on the cheap side. Peter's been building online marketplaces for a while, and he'll teach you how he approaches setting up profitable businesses. 00:00:…
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Dashiell Bark-Huss is incredible. She lived in a van for three years, where she taught herself to code. She created WishTender as a solo developer after a friend suggested it would be useful. After Dashiell launched, her spouse began working with her, and they have bootstrapped the business to 50k+ users in 1.5 years. WishTender is an international…
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Here are my personal strategies for achieving consistency in content creation, which encompass implementing accountability systems, connecting with my audience, and reaping financial and lifestyle rewards. Additionally, I explore the difficulties of maintaining motivation and the vital role of community in this process. I recount my own story, begi…
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Noah enjoys programming challenges as well as developing new and unique apps. CoffeePass and Supportman are two startups he co-founded and sold. And is experienced as a web/mobile developer at four different companies. He is currently working on Potion, a Notion-based website builder. Potion.so adds the magic, resulting in a fast site with custom d…
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