ProfitLed Podcast

Hey, it's me again, Melissa, back for Season Three. I'm the cofounder and CEO of eWebinar, and your host here at ProfitLed. This episode is the backstory behind this season's theme: Passion, Profit, and Purpose, and how those three things shift as founders come into financial success.

About a year and a half ago, after 14 years as a 3x bootstrapped founder, I hit a wall. I lost my inspiration, my motivation, and somewhere along the way, myself. From the outside, everything looked great. Profitable company, loving partner, life on my own terms. But inside, I was unraveling.

What I went through forced me to look at a part of the founder journey we almost never talk about. We spend so much time on growth strategies, marketing hacks, and the numbers, and almost no time on the person running the company. But the most important variable in any startup's success is you. And what you want, what drives you, and what success even means to you doesn't stay fixed. It shifts as you evolve. Your business stays constant and demanding, but you don't.

That's what Season Three is about. The conversations we don't have enough of. The ones about what happens after you've built the thing, found some financial security, and look up and ask, now what?

If this resonates, and you're curious how other founders have navigated this human journey, this season is for you.

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

It took eWebinar 16 months to go from idea to product launch, then another 36 months to hit $1M ARR; this is the core theme of this season. That's a total of 52 months from incorporation date.

You might have read about companies that get to $1M in a year, much less now with AI startups and the world riding that wave. Those are outliers and not the norm. 36 months to $1M is actually the median, even for funded companies.

“Normal” is not newsworthy and doesn’t get the media spotlight it deserves so you might feel like you’re moving too slow even when you’re in the right place.

On this season finale episode, Melissa and Todd dive into the 12 most shocking surprises on their way to $1M ARR after everything they tried, learned, and failed, which formed the foundation by which they continued to iterate on the business and product.

Thank you for tuning into Season 2 of ProfitLed!! Your support is deeply appreciated.

If you enjoy this podcast, please consider leaving us a review as that will help us continue to make episodes for you. 

Takeaways:
• Things they thought would have a huge impact, but didn’t
• Assumptions that made them think they’d get to $1M faster
• Things that took a lot more effort and time than anticipated
• Why you don’t need fancy metrics to prioritize roadmap
• Why $1M is not the magic number even though it seems like it is

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

“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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.

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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

This podcast was brought to you by eWebinar:

Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com, no salesperson required.