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20VC: One Question Founders Must Ask Themselves When Approaching Investor Selection, Why Series B Is One Of The Most Challenging Phases & What Makes For A Successful CEO Transition with Jeff Russakow, CEO @ Boosted

Apr 5, 2019

Jeff Russakow, CEO of Boosted, a pioneering electric skateboard startup, shares his journey from leading enterprise companies to rethinking urban travel. He discusses the crucial question founders must ask when selecting investors and the common pitfalls they face. Jeff elaborates on the challenges of Series B fundraising, focusing on balancing unit economics with a long-term vision. He also critiques the notion that "hardware is hard," advocating for a richer understanding of product challenges and innovation in transportation.

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ANECDOTE

Return to Robotics

Jeff Russakow transitioned from Fortune 500 companies to Boosted's CEO mid-career.
This was a return to his robotics roots after years in software and digital media.

ADVICE

Mid-Sized Growth Companies

Consider mid-size growth companies for career development.
They offer established systems and mentorship while still experiencing rapid growth.

INSIGHT

Funding Trends

VC funding has shifted from seeking one massive hit to prioritizing consistent returns.
There's less focus on hardware and more on SaaS due to recurring revenue models.

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Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo.

In Today’s Episode You Will Learn:

1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted?

2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here?

3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously?

4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it?

5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: The Missing Piece

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