Episode Recap

Doug Knopper spent 17 years leading advertising technology companies such as DoubleClick, which was acquired by Google for $3.1 billion in 2008, and FreeWheel, which Doug co-founded and served as co-CEO, and which was acquired by Comcast for $375 million in 2014. Doug spoke to me about what he learned about leadership in these roles and about his new project, CEOhacker, which teaches the young Silicon Valley CEOs of today the skills they’ll need to lead successful companies tomorrow.


The benefit of experience
When Doug started FreeWheel with his co-founders, they were established and experienced leaders with deep networks, helping them to attract executive talent almost immediately. They also knew enough to know that FreeWheel would need a vision from Day One.

Benefit from Doug’s experience:

  • If you don’t have a network, make one. Go to every conference, speak to every VC — everyone knows someone who is looking for their next role and might be a good fit for your new company’s burgeoning executive team.
  • But also look beyond the old boy network. FreeWheel set out to hire and promote diverse talent from the beginning and prides itself on its culture of inclusivity. This goes all the way to the top: co-founder Diane Yu is a rare woman founder in Silicon Valley


The eternal struggle: how does a technical CEO find a VP of sales
Co-founders Doug and Jon Heller served as co-CEOs of Freewheel, which allowed them to fill many top sales roles themselves in the company’s early stages and take their time finding the right VP of sales — ideally someone promoted up through the company.

Benefit from Doug’s experience:
One of your first hires should be a talented but inexperienced sales person you can groom into the VP role. Create your own VP of sales rather than hire one from outside.


The hardest hire
Many think it’s the VP of sales, but Doug says it’s the head of marketing. The pool of qualified candidates is smaller and most of them are already working at established companies and won’t want to risk moving to a startup.

Benefit from Doug’s experience:

  • Again, Doug says your best bet is to find someone young and inexperienced but talented you can take on in a more junior role and groom up to lead your marketing team.
  • Don’t do this if you aren’t willing and able to mentor, shape, and groom those less experienced hires. Without your guidance, they will fail. So might your company.


Money and vision but no idea what to do next
Silicon Valley is full of young, inexperienced CEOs who have been trusted with millions of investor dollars despite not knowing CEO fundamentals:

  • running a board meeting
  • making a business plan
  • building and retaining a team
  • creating a company culture
  • juggling the needs of goals of investors, customers, and employees.


Benefit from Doug’s experience:
That’s why Doug created CEOhacker — to “crack the code” of being a successful CEO and scaling your business. It’s especially important to him that women and people of color who have little representation in Silicon Valley have access to these tools.



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DoubleClick acquired

FreeWheel acquired

Silicon Valley’s diversity problem

FreeWheel’s commitment to diversity