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On Season 2, Melissa Kwan (Cofounder of eWebinar) and Todd Parmley (COO) relive their "Journey to $1M" ARR, bootstrapping eWebinar from day one. Each episode goes in depth into one major aspect of the journey, as Melissa and Todd share war stories, mistakes, and lessons learned as they grew the company to a million in annual recurring revenue, over a period of 36 months from product launch. If you’re a bootstrapper who wants a window into the day-to-day lives of other scrappy bootstrappers navigating the realities of building a successful company – the good, the bad, and the ugly! – this podcast is for you. __ ProfitLed is a podcast by and for bootstrapped founders brave (or crazy) enough to grow their businesses to profitability without venture capital. There’s so much content out there featuring VC-backed founders and the unicorns they ride. But everyone else? Not so much. ProfitLed is dedicated to sharing the hard-won experience of bootstrappers in order to inspire fellow bootstrapped entrepreneurs to grow their own businesses and propel themselves closer to the freedom they’re working so hard to achieve. Presented by: eWebinar - https://ewebinar.com

Location:

Canada

Description:

On Season 2, Melissa Kwan (Cofounder of eWebinar) and Todd Parmley (COO) relive their "Journey to $1M" ARR, bootstrapping eWebinar from day one. Each episode goes in depth into one major aspect of the journey, as Melissa and Todd share war stories, mistakes, and lessons learned as they grew the company to a million in annual recurring revenue, over a period of 36 months from product launch. If you’re a bootstrapper who wants a window into the day-to-day lives of other scrappy bootstrappers navigating the realities of building a successful company – the good, the bad, and the ugly! – this podcast is for you. __ ProfitLed is a podcast by and for bootstrapped founders brave (or crazy) enough to grow their businesses to profitability without venture capital. There’s so much content out there featuring VC-backed founders and the unicorns they ride. But everyone else? Not so much. ProfitLed is dedicated to sharing the hard-won experience of bootstrappers in order to inspire fellow bootstrapped entrepreneurs to grow their own businesses and propel themselves closer to the freedom they’re working so hard to achieve. Presented by: eWebinar - https://ewebinar.com

Twitter:

@profitledfm

Language:

English


Episodes
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S2E27 The 12 Most Shocking Surprises on Our Way to $1M ARR

3/25/2025
When Melissa cofounded eWebinar, she had no idea it was going to be “product-led”. Before becoming an entrepreneur, she had always been in B2B sales and biz dev roles. She was always a sales-led founder as both her previous startups were enterprise SaaS. The word “product-led growth” didn’t even exist in her vocabulary! When she ran out of leads to sell to in her network 9 months after launching eWebinar, she asked other founders for help. You can imagine her surprise when she learned that low cost, self-serve SaaS products were sold in a completely different way. Turns out, people don’t pick up the phone for $99/month products; they prefer to do their own research and sign up at their own pace. On this episode, Melissa and Todd dive into the 9 most important PLG (product-led growth) lessons learned as they powered through and figured things out by trying everything under the sun from playbooks, experts, and friends. Takeaways: • Marketing strategies that worked, and ones that didn’t • Why you should invest in high quality, engaging content • Why customers aren’t always your greatest source of info • Hardships and beauty of making a self-serve SaaS startup work Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInyour founder next door@themelissakwanInstagramYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:46:53

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S2E26 9 Most Important PLG Lessons Learned

3/11/2025
When Melissa cofounded eWebinar, she had no idea it was going to be “product-led”. Before becoming an entrepreneur, she had always been in B2B sales and biz dev roles. She was always a sales-led founder as both her previous startups were enterprise SaaS. The word “product-led growth” didn’t even exist in her vocabulary! When she ran out of leads to sell to in her network 9 months after launching eWebinar, she asked other founders for help. You can imagine her surprise when she learned that low cost, self-serve SaaS products were sold in a completely different way. Turns out, people don’t pick up the phone for $99/month products; they prefer to do their own research and sign up at their own pace. On this episode, Melissa and Todd dive into the 9 most important PLG (product-led growth) lessons learned as they powered through and figured things out by trying everything under the sun from playbooks, experts, and friends. Takeaways: • Marketing strategies that worked, and ones that didn’t • Why you should invest in high quality, engaging content • Why customers aren’t always your greatest source of info • Hardships and beauty of making a self-serve SaaS startup work Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInyour founder next door@themelissakwanInstagramYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:45:02

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S2E25 What Lifestyle Business Means

2/25/2025
“This is fine as a lifestyle business.” Says every VC with a slight look of disdain after you pitch them your brilliant idea they don’t want to invest in. The industry has given “lifestyle business” such a bad reputation by commonly using it to describe non-venture scalable businesses with less ambitious founders. Only 1% of startups are venture funded, which means the other 99% are bootstrapped and by industry standard, lifestyle businesses. If anything between zero and unicorn is “lifestyle”, I’d happily take it. eWebinar was founded intentionally as a lifestyle business, and that means choosing happiness over revenue for all decisions as it relates to the wellbeing of every team member, product, pricing, customer support, operations… On this episode, Melissa and Todd discuss what a “lifestyle business” is for them, and the things they do to achieve the dream company that gives everyone involved (not just the founders) a great lifestyle. Takeaways: • How the industry and VCs (negatively) perceive lifestyle businesses • Melissa’s 10 non-negotiables to happiness that led her to found eWebinar • Intentional decisions we make to achieve our dream lifestyle business • How choosing happiness over revenue impact product, operations and team • The culture we try to create at eWebinar and what it’s like to work here Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInyour founder next door@themelissakwanInstagramYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:44:37

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S2E24 5 Pricing Decisions that Turned Out to be Costly Mistakes

2/11/2025
Should you “do right by your customers” at the expense of the company, your team, and your own wellbeing? Your answer might be “yes”, until you realize a small change that customers would barely feel could mean instant profitability for your bootstrapped startup. Having said that, hindsight is always 20/20. There are some mistakes that you just have to make yourself, no matter how many warnings you get. On this episode, Melissa and Todd share the five pricing mistakes they made, why they were so costly (including one that would’ve given them $30k/month overnight), and what they could have done differently. Takeaways: • The pros and cons of not offering annual plans • Why you need to put usage limits on your trial period • Why “being fair” has little to no impact for your customers • Why you shouldn’t grandfather and increase pricing across the board • The importance of understanding every cost that drives your platform Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:46:02

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S2E23 Why We Stayed Away from Enterprise

1/28/2025
Most companies think the answer to more revenue is to sell enterprise, but they aren't aware of the massive hassle and costs that come with going upmarket. There's no such thing as free money. The bigger the deal, the more attention you need to give your customer. The more customizations you offer, the more versions of your product you have to maintain. Many founders think the air is better up there because they think it'll solve their money problems. Spoiler alert: It won’t. On this episode, Melissa and Todd discuss all things enterprise sales and why they stayed away from it, and why they think you should too if you have a good thing going with self-serve SaaS. Takeaways: • What we learned from spending a decade selling to big companies • The not-so-hidden costs of enterprise: sales, operations, product • Why going upmarket is not always a path to more revenue • Things you should consider before going upmarket Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:57:25

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S2E22 5 Wrong Hires that Ended Up Costing $450k

1/14/2025
Hiring is one of the biggest challenges every company faces. For bootstrapped startups, this challenge is even bigger as we have to compete against funded companies and tech giants. Part of building a startup is trial and error, throwing things against the wall to see what sticks. Hiring is no different - it’s a learning process that can sometimes get expensive if you don’t “fire fast”. On this episode, Melissa and Todd dives into their 5 most costly hiring mistakes, what happened, and what they learned from each experience that helps them better define job requirements and run interviews in the future. Takeaways: • The profile of people startups should never hire • Why marketing agencies can’t take a company from 0-to-1 • When dev shops make sense (and when they don’t) • What “firing fast” means and why it matters for startups • Hard lessons we learned about hiring and firing Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:58:12

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S2E21 When Our Startup Became a Real Business

12/10/2024
eWebinar was built in a silo for 18 months before the first person signed up for a trial. Melissa and her team had no idea if this business would become “real”, and if people were going to pay for the service. On this episode, Melissa and Todd recount stories of when they knew they were onto something, through customer interactions and feedback, outgrowing their marketing website, and hitting scaling issues from increased usage. Takeaways: • Signs of our business business becoming “real” post launch • How customers, marketing, and pricing changed as business grew • Product enhancements we had to do as a result of scaling issues • How growth changed the way we approached the business Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:43:12

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S2E20 Social Selling and Personal Branding

11/26/2024
If you’ve been following Melissa on LinkedIn, you’ll know that she’s a frequent contributor on the platform, sharing lessons and stories from her journey bootstrapping three startups. What you might not know is the backstory of WHY she turned to social selling after running out of leads to sell to. On this episode, Melissa shares her “hacks” of building a content machine starting with taking Justin Welsh’s “LinkedIn OS” course, how she experimented with different content styles, and eventually found her own. Wondering if all this effort was worth her time? Hear Melissa dive into the benefits and ROI of spending time writing content, which goes far beyond building an audience who she hopes to one day sign up for eWebinar. Takeaways: • Why I turned to LinkedIn when we ran out of leads • Why your personal brand matters now more than ever • How I went viral on LinkedIn 8 weeks in a row (the good old days!) • 11 “hacks” to build your own content machine and get engagement • The benefits of writing content, social selling, and personal branding Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:44:50

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S2E19 12 $0 Marketing Strategies

11/12/2024
Spending money on marketing is often not an option for bootstrapped startups, at least not enough to make a meaningful impact. Without an abundance of resources, there’s no choice but to get creative. While found-led sales can get you off the ground, your network can exhaust pretty quickly, leaving you with the challenge of figuring out new ways to generate demand. On this episode, Melissa and Todd share the 12 most effective zero-dollar marketing strategies that got eWebinar to $1M ARR. Takeaways: • Why paid marketing should be your last resort • How to create evergreen content that lasts forever • 12 $0 strategies you can steal to grow your own business Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:01:08:52

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S2E18 The Customer is NOT Always Right

10/29/2024
Companies like Amazon and Costco who pride themselves on customer service conditioned consumers (me and you) to think that customers are always right - but, are they? In the faceless world of software, customer demands can be brutal, leading to soul crushing and demoralizing support. Training your customers to respect your team and product sets the foundation for healthy business relationships that make you feel appreciated. On this episode, Melissa and Todd recount customers from hell, the things they did to try and get around paying for the service, and how they dealt with demanding and rude customers. Takeaways: • What happens to your business when the customer is always right • Our customer horror stories and what they did to game the system • How we set expectations for customer relationships • How to deal with customers from hell Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:48:25

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S2E17 You Pay Peanuts, You Get Monkeys

10/15/2024
15 years ago, Dropbox spread like wildfire with their freemium product and that gave us the impression that free = more users. It deluded companies to think that giving something away for free is a go-to-market strategy, when it’s far from that. Giving away something for free has many negative implications that aren’t often talked about. The most irritating one being the fact that it attracts the worst customer profiles. The people who are least tech savvy, most time consuming on support, and never end up converting. On this episode, Melissa and Todd share stories about the different campaigns they tried to get users into eWebinar and why removing price friction is one of the worst things you can do for your business.. Takeaways: • How price perception affect how people evaluate products • Types of users who have never activated on our platform • Why free users are the worst and suck all your time and energy • Reasons we no longer offer discounts, no exceptions • What happened when we charged more and shortened trial period Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:35:37

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S2E16 Our $130k Mistake in Affiliate Marketing

9/24/2024
If you have a great product and offer a commission for people to promote it, they’d happily do it and you’d just make money, right? Not so fast… On this episode, Melissa and Todd recount the painful memories of spending $130k on affiliate marketing over 10 months; an experience Melissa considers the “biggest financial mistake she’s made in her career”. Takeaways: • Why we jumped into this channel too early • Reasons why this strategy was a colossal failure for us • Why you should stay away from affiliate marketing (for now) • The complexities of affiliate marketing nobody told you about • Things you need in place before affiliate marketing might work Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:35:43

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S2E15 How We Decided on Our Roadmap

9/10/2024
Everyone says you need to measure everything so you can make data-driven decisions on your product. That's exactly the strategy eWebinar DID NOT follow, especially when there's not going to be enough data when you don't have enough users. On this episode, Melissa and Todd shares how they decided on priorities even before having a significant customer base, and the lean process their product team goes through to execute on feature development and roll out. Takeaways: • How we came up with an initial wishlist as a guideline • How we prioritized by listening to customers (but not always) • Why we didn't measure anything nor make data-drive decisions • The process of deciding on features per quarter and executing • Things we do that are significantly different than large companies Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:45:37

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S2E14 10 Go-to-Market Strategies that Didn't Work

7/30/2024
Running a startup is a lot of throwing things against the wall to see what sticks (and what doesn't). The hard truth is, majority of things you do won't work...but you need to do them anyway to find the few things that do. On this episode, Melissa and Todd dives into the 10 go-to-marketing strategies that didn't work for them, why, and what they learned from each one. Takeaways: • Think twice before putting effort into Product Hunt. • Things they wasted too much money on too early. • What they thought would have a huge impact, but didn't. • Should you pay to be in a newsletter with massive reach? • There are a lot of things you think will move the needle, but do they? Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:34:14

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S2E13 Owning SEO When Marketing Agencies Suck

7/16/2024
In the last 13 years, Melissa has worked with over 10 marketing agencies/contractors to execute a content strategy. Most couldn't deliver on their promise. It was incredibly frustrating. You may have experienced something similar. The vicious cycle went something like this: → Hire company experienced in digital marketing for min 3-6 months → Get proposal of new content strategy because old one was bad → Technical and content audit, keyword research → Receive mediocre pieces of content → Realize company is not a good fit → Start over after spending $10k+ Most writers wrote for the sake of generating more clicks without a deep understanding of our business and customers. As a result, their content was basic and boring. Most pieces were not written for the advanced business users they wanted to attract. Melissa and Todd finally decided to take back control and learn SEO and content writing from the ground up. Takeaways: • Why marketing agencies suck • The importance of owning your SEO when it's a primary revenue source • Benefits of knowing how SEO and content works • How to own your SEO, and skills required • Companies that can help you on this journey Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:47:25

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S2E12 Staying Super Duper Lean

6/25/2024
Melissa and Todd talks about how they stay super lead as a bootstrapped startup, how they decide what to and what not to spend money on, and how to avoid money mistakes they've made in the last few years. Takeaways: • What "lean" means especially for bootstrapped startups • The importance of optimizing cost versus being cheap • What to spend money on (software, people, operations) • What not to spend money on until absolutely necessary • Money mistakes they made and how to avoid them Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:45:12

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S2E11 Leveraging Customers to Sell Our Product

6/11/2024
Melissa and Todd talks about how (and why) they leveraged their best customers to sell and market eWebinar by using the language they used to describe value propositions and how the product solves their problems. Takeaways: • The moment Melissa realized 1on1 sales was never going to cut it • How to extract the best product marketing language from your customers • The process of doing customer interviews and deep dives to create a database of marketing language • Identifying your best customers and creating an "Ideal Customer Profile" (ICP) • What to do with the content you extract and how to get help • Why this is the most valuable exercise you can do for your startup Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:41:01

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S2E10 Importance of Founder-Led Sales

5/28/2024
Founder-led sales is the ONLY way to get your startup off the ground. If you can't sell your own product, how can you expect someone else to? On this episode, Melissa digs into why every founder needs to be the first to sell their product, and how anyone can learn how to sell today. Takeaways: • Where to find your first set of prospects to sell to • Using sales as a way to get customer feedback • Separating good feedback from bad • Using objections to prioritize your roadmap • Disconnect between what you're selling and they're buying • Verifying/discrediting assumptions about the product • How anyone can learn how to sell by using my demo script Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:58:40

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S2E9 Product Launched, Now What?

5/14/2024
Launching eWebinar after 18 months was a huge milestone, but then what? On this episode, Melissa and Todd discuss what it was like to wake up from the dream that if you build it, they'll come. Spoiler alert: That didn't happen. Takeaways: • When reality set in after months of daydreaming • Product assumptions that worked and didn't work • Initial user reactions, the good, the bad, and the ugly • Why the market wasn't as ripe as they thought • Things that went well and things that didn't • Realizing people didn't always understand the solution • What to do when it's going to take way longer to hit profitability than anticipated Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:44:48

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S2E8 Launching Our MVP and Converting 85% of Trials

4/30/2024
Melissa and Todd dive into the thrilling and nerve-wracking experience of launching eWebinar's MVP. While many people see product launches as the end goal and celebratory occasion, Melissa explains why it's often more stressful instead because that's when the dreams you've sold become reality. They reminisce about getting stuck in a never-ending rabbit hole of features, how frustrated David (CTO) was, and how they ultimately had to choose a launch date just to get the product out the door. Melissa recounts the fascinating experience of seeing users (webinar attendees) interactive with eWebinar for the first time and the pressure she felt from her startup finally coming to life. Tune in and learn how Melissa got their first trial users on board, and how they ended up converting 85% of those users at the first billing date. Contact ProfitLed @profitledfmProfitLed.fm Connect with our host Melissa KwanLinkedInInstagramTikTokTwitterYouTube This podcast was brought to you by eWebinar. Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar. Thanks for listening!

Duration:00:38:06