How to Raise a Round Podcast: Craig J. Lewis, Gig Wage

How to Raise a Round Podcast: Craig J. Lewis, Gig Wage

Author: Josh Durst-Weisman
Read time:  2 minutes
Published date:  September 9, 2021
In this episode of How to Raise a Round, we hear the story of Craig J. Lewis, and learn how he led his company Gig Wage to a successful $2M seed round.


After fielding endless criticism and navigating a pivot, Craig Lewis, Founder and CEO of gig economy payroll platform Gig Wage, found success in perseverance. 

The Dallas-based company raised a $2 million seed round in November 2018. But the road to success wasn’t without its fair share of roadblocks. 

A few years ago, Gig Wage was at an inflection point. They’d burned through their $750K pre-seed funds working on an initial idea, but having made slower progress than they initially expected, Craig was now feeling a pull from angel investors to call it quits and shutter the business. 

However, where other founders may have been paralyzed, Craig simply isn’t built like that.

Over the next few weeks, he began navigating his team through a pivot, heeding signs from the universe that he was on the right track when he found a contractor willing to write the first lines of code and a yoga studio willing to pay Gig Wage to payroll its instructors. 

This is what Craig calls the “peek into possibility,” and it created the small spark of traction that Gig Wage needed for their next funding round. 

Opportunity struck at exactly the right moment. When a larger company came knocking on Craig’s door to explore a potential acquisition, he smartly used it as an opportunity to prove Gig Wage’s market value. The acquisition never went through, but the interest created “FOMO” and renewed the attention of other investors. 

In this episode of How to Raise a Round, Craig shares this key takeaways from his funding journey.

“The thing that I think I’ve been good at more so than continuing to power through failure, is leveraging each moment that I’m in and almost hedging and amplifying the opportunity to make sure I don’t lose. You can fail, but that doesn’t mean you lose.”

In the episode, we learn:

• How Gig Wage rebounded from near failure

• Why a ‘no’ from an investor isn’t really a loss

• The advantages of a party round 

• The intricacies of assigning pre- and post-money valuations

Listen to our interview with Craig J. Lewis by streaming How to Raise a Round on Apple Podcasts, Spotify, or wherever you get your podcasts. 

Josh works in marketing and sales at Carta. Prior to tech, he spent several years in Los Angeles as a TV producer and writer of bad horror movies.