Moonlighting has all of the pieces in place to be a highly successful company and is one that we are bullish on the future of. The founder Jeff Tennery, has spent his whole career in the mobile and media space. His career has included stops at AOL as SVP of mobile advertising, VP at nTelos Wireless in the Sales & Ops division and as VP of Sales & Marketing at AT&T.

This seasoned executive turned startup founder has already amassed $6M in funding from major media entities such as Tribune and Gannett to name a few and has grown its user base to over 650K users. What he and his team are doing is creating a marketplace for the gig economy that doesn’t price gouge its users and in doing so is creating a true competitor to the likes of Upwork and Thumbtack that are already billion dollar unicorns.

After speaking with Jeff, I am even more bullish on the opportunity as his vision and mindset for the business show signs of leading to true market differentiation.

Funding Round Details

Moonlighting logo
Company: Moonlighting
Security Type: SAFE
Valuation: $28,000,000
Min Investment: $100
Platform: Republic
Deadline: Dec 31, 2018
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Jeff, you have spent your career across major telecom brands and working for mobile ad-tech startups like Millennial Media. How have these experiences shaped your approach to building Moonlighting?

I was born into the mobile business in the mid 80’s and have grown with the industry since its inception.  I climbed some of the first cell towers and tested the first brick phones on the lawn of the Whitehouse. In early 2000’s I saw that the business shift from a network carrier business to a media and content business.  I spent time working with venture backed companies that were ushering in the mobile internet through mobile apps and made the pivot with the industry.

Moonlighting is really a compilation of all I have done over my 30 year career. It’s a platform that allows people to connect via a mobile application to conduct business and be a part of a large global community. I am incredibly proud that Moonlighting allows me to utilize all that I have learned and achieved and the fact that we built a company that helps people makes it all the more rewarding.

From Thumbtack for blue collar gigs to Upwork for white collar gigs, how does Moonlighting differentiate to other freelance platforms?

We always wanted Moonlighting to be more inclusive than the other niche platforms to empower our users to use it as they needed.  We focus on tools that entrepreneurs and freelancers need to not only find clients but to engage them on an ongoing basis. SaaS features that enable our users to get discovered, get hired and get paid very quickly.  

We also feel very strongly that freelancers should keep 100% of the earnings.  Some of these platforms are taking 20%+ of a paycheck and we don’t think that’s fair.  We set up a very affordable monthly subscription model so freelancers can effectively budget and focus on using our tool set to engage their clients.

To date you have had significant success with over 600K registered users on your platform. How have you acquired these users and do you have a sense of CAC?

Our background is steep in mobile user acquisition and digital performance marketing so we have been able to acquire customers at a sub $5 level.  We also leverage our strategic partnerships with leading local news media companies Gannett, Tribune and McClatchy where you will find Moonlighting offers in such iconic news sites like the LA Times, Chicago Tribune, Miami Herald and USA TODAY.  

This gives us additional marketing exposure along with the partnership we have with Verizon where they market our services to their small business group and pre-load our app onto select Android devices

What does the retention rate of freelancer’s look like on the platform?

The results are still early as many of our users have opted to sign up for our 1 year membership.

Can you talk about how this business scales internally and what avenues you see to reach the 6M users you’d like to have on the platform in a couple years time?

We are expanding globally and have launched our platform in Canada and will enter the UK by year end. We are raising money from traditional venture funds, several of which are located in EU and Asia to help us expand the platform globally by end of 2019.

You have mentioned interest in bringing blockchain and tokenization to the Moonlighting platform. Why do you think this type of tech has a place in the gig economy marketplace?

Blockchain technology allows companies to disrupt business models where a middle man takes a cut of a transaction. Our platform is already a P2P platform (peer to peer) and we have been disintermediating traditional staffing and recruitment companies since our inception in 2014.   

Blockchain and issuing our own cryptocurrency will eliminate expensive bank and foreign exchange fees as we expand the platform globally giving us a distinct competitive advantage over incumbents like UpWork and Fiverr who, along with recruiting firms and staffing agencies, will have a tough time shifting their model.  

Why have you not pursued an ICO to date if that is the plan and do you worry it could hinder a future acquisition from a more established player?

We have retained top counsel and advisors who come with a wealth of knowledge and experience and they advised us to postpone our ICO.   We were preparing to conduct an ICO in Q1 but refrained as we felt like the longer we wait the better off we will be.

Our goal is to expand the platform globally, and build our audience up into the millions so that our token will have true utility.  We are not concerned with a future acquisition being hindered by an ICO as we believe that many leading companies like Apple, Amazon and Facebook will eventually tokenize their user base.  

I think companies that conducted legitimate ICO’s that have a scaled customer base, real revenue and usage like Moonlighting, will always be attractive to acquirers especially those who don’t have a credible blockchain plan

What additional capital do you need to raise to obtain your growth goals and what will the structure of the team be?

In today’s start up world, it’s important that companies consider multiple options when raising money.  At Moonlighting, we have raised $6.3M to date using equity and debt financing and now a Reg CF campaign with Republic.  We also have a token strategy, both security and utility coins, and will look to deploy those in 2019.

Do you see your business as a potential acquisition target for larger freelance boards like an Upwork?

The industry is evolving as the gig economy is becoming more credible by the day.  Moonlighting is well positioned to take full advantage of the tailwinds of freelancing and blockchain technology.  We have been approached about acquisition but feel like its early given the headroom in the freelance industry.

UpWork announced their IPO intentions with their S1 and Fiverr has been rumored to be considering a public offering as well. These are all good signs for the industry and will cause traditional recruitment and staffing companies to consider M&A as a way to get into the space.  

From an industry perspective how do you think the freelance economy marketplace industry will shake out over the next 5 years and where does Moonlighting fit into that?

The gig economy is still very nascent and early and its also very fragmented.  Our goal has been to build a company that could bring the gig economy mainstream. The press has called us Craiglist without the creepiness which is humorous and flattering in the same breath.  

Craigslist is probably the closest to a mainstream winner in the space but does lack tech features for many segments of the gig economy. We have addressed many of those gaps which is why we are so bullish on our position and ability to become the next mainstream winner and household name for employment.

For those curious about the valuation, how did you determine the $28M valuation?

We are backed by the largest news media companies in the US who led our last round.  They looked at our user base growth, engagement, business model, conversion metrics, CAC and customer LTV and came up with a post money from our last round.  

We placed a modest increase on that valuation and launched this round to get our users involved.  We want our user base to be owners which is why we are running this campaign with Republic. And in 2019, our goal is to conduct a token sale that will allow them to participate again.

Be it a major acquisition or a standalone business, we think Moonlighting has the makings of being a major success for equity crowdfunding investors. Their roadmap and international expansion plans are going to drive the type of growth profile we look for.


Stay tuned as we will be deep diving on Moonlighting even more in the coming days. And be sure to invest HERE.