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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!

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

• Tweet us at @profitledfm.
• Find show notes of each episode on ProfitLed.fm.

Connect with our host

• Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
• Follow @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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!