"There seems to be some perverse human characteristic that likes to make easy things difficult."

- Warren Buffet

Numerous Issues...
We Have a Solution

  1. Too much capital too soon – Optimal amount of capital to drive profitable growth.
  2. Limited operator experience and unfulfilled value-add – We are operators. We get it. We have bona fide functional expertise.
  3. Endless rounds of capital  – Growth-to-exit. We are intentional about working toward an exit in 2-3 years. 

Growth-to-Exit Strategy


  1. Every business has specific windows to sell to a strategic or financial buyer.
  2. These windows don’t stay open forever; you gotta be intentional.
  3. We have experience across various types of exits to know the paths and pitfalls (IPO, Strategic, Private Equity, etc. )
  4. We are maniacally focused on aligning with founders on a 2-3 year exit strategy.

A Little About Us

SkyLab is a combination of an innovative VC fund, a modern marketing agency, and an influencer marketing network.





Jesse Silva is an investor, venture capitalist, entrepreneur and operator. Starting from a lower- middle class background, Jesse founded a small towing company and worked three jobs to support it. Over a number of years, he completed more than 100 acquisitions and grew Alpha Towing to over a $125M valuation. Jesse sold the company and attract-ed the interest of financial institutions and national brands to replicate his successful systems and structure. He has consulted as an asset manager in risky acquisitions, consulted with Little Caesars, invested in startups, and started a high-end vehicle wrap shop. Jesse is an expert at scaling, fund and asset management, c-suite staffing and management, acquisitions, systems and logistics.

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Benson has a uniquely well-rounded career. He is known as a talented company builder, investor, and operator. A former Bain & Company strategy consultant, PE investor and, most recently, a tech company COO, Benson is a turnaround specialist, growth-oriented executive, and someone who is a problem solver with a nose for value. He has been a trusted advisor to some of the world's largest companies as well as a startup executive and board member. In the last few years, Benson helped lead Pluralsight's IPO (Utah's largest todate) as well as the strategic sale of SaltStack to VMware. He is both driven and nimble; a genuine leader of people. Co-Founding SkyLab with Jesse Silva is convergence of Benson's diverse career experience.











Interested Yet?


Bobby is a seasoned M&A and fundraising professional. Prior to joining SkyLab Ventures, Bobby worked at SaltStack, a B2B infrastructure software company, where he played an important role in the Company’s financing strategy and eventual strategic sale to VMware. Before SaltStack, Bobby spent time as an investment banker at Raymond James in their Technology & Services group and is responsible for assisting in over 10 successful M&A and capital raising transactions cumulatively worth over $1 billion in transaction value. Bobby started his career as an analyst at Peterson Partners, a middle-market private equity firm in Salt Lake City.

Connor Jenkins

Connor Jenkins is an operator and logistics specialist. Prior to joining SkyLab Ventures, Connor had managed a large real estate portfolio, built out sales and logistics infrastructure for a tech startup, and consulted Mercedes Benz covering over 130 dealerships maximizing opportunity across their sales and marketing operations. Connor has a unique ability to look into a business and problem solve, which makes him a valuable asset here at SkyLab.

Greg Woodward

Greg is one of the most accomplished business leaders in Utah. Greg has been at the forefront of building some of the greatest success stories in the last 15 years. He was a founding member of Huntsman Gay Global Capital (HGGC) where he was a leader in portfolio operations and helped drive significant exit valuations in their $1.1B debut fund that propelled HGGC to its second fund. He was CFO and COO of Pluralsight overseeing 8 acquisitions and multiple rounds of debt and equity capital including the largest venture capital round in the State of Utah at the time. Since then, Greg has developed an impressive portfolio of investments, board seats and advisory roles to help the next wave of startups and funds. As an advisor to SkyLab, Greg has been a huge voice in the strategy and positioning of the fund and in the ongoing execution.


Daryl was a founding and principal engineer at Qualtrics. Over his 13-year tenure there, Daryl helped the company grow from a basement startup into the most successful software company in Utah history culminating in an $8 billion acquisition by SAP in January 2019. Serving in various engineering and product management positions, Daryl made significant contributions to many of Qualtrics’ most successful product lines including Research Core, Digital Experience, Customer Experience, XM Directory, and Employee Experience – a portfolio of products with a combined revenue (ARR) in 2019 of more than $400 million.


Spacestation Integrations is a top influencer marketing agency focusing on connecting YouTube, Instagram, and TikTok creators with world-class brands. In 2020 the Utah-based team paid creators over $11M and generated millions in sales and billions of views for the brands. As a SkyLab partner, Spacestation Integrations adds influencer marketing strategy to portfolio companies. See their work at https://spacestationintegrations.com

Tim Holladay

Tim joined the Spacestation in August 2019 as the managing partner for Spacestation Investments, an early stage angel investment team. In addition to funding the famed Spacestation Gaming esports organization, Tim has led investments in Magic Spoon, Olipop, Giggster, Koia, Evercast, Kinder Beauty and 25 more. Tim specializes in connecting SkyLab portfolio companies with influencer marketing strategies for explosive growth. Prior to the Spacestation, Tim and his brother Sean built and sold their startup Crowd Mics to Biamp.


Entrepreneur and investor in people. Derrick founded Extreme Staffing in 2010 and exited in 2020 in the top 7% of largest agencies in the nation. Over the past decade, Extreme Staffing helped hundreds of companies and tens of thousands of employees build better futures finding careers. Leader in organizational development, how companies should hire successfully and build company culture. Derrick invests in and sits on the board of several successful start ups.

Sean Holladay

Better known as Holladay, Sean is co-founder of The Spacestation. In 2017 he built Spacestation Integrations which has become one of the most innovative and fastest growing influencer marketing agencies in the country. Holladay struck the first influencer deal with Mattel to create two custom Hot Wheels cars. He partnered with Nomatic and launched a $2.4 million KickStarter campaign for the top YouTube photographer Peter Mckinnon. Spacestation Integrations paid creators over $11M in 2020. SkyLab benefits from Holladay’s genuine relationships with top influencers, companies and investors. Prior to founding the Spacestation, Holladay was the co-founder of Crowd Mics, which sold to Biamp in 2016.

Chandler Welling

Over the last 10 years, Chandler has been leading creative and customer acquisition for some of the internet’s biggest brands, most notably Snow Teeth Whitening who went from startup to $100M+ in two years. 

Having successfully deployed tens of millions of dollars across Facebook, Instagram, Google, and Snap; Chandler is no stranger to customer acquisition at scale. Chandler’s unique view on creative, paid media, and innovative products and services made his addition to the Skylab team a foregone conclusion.