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Episode Audio

Featured Interview/Opening Discussion

In our first interview every on the show we sit down with none other than HD Moore, founder of the Metasploit project and currently Principal at Special Circumstances, LLC. In the Startup News this week, the differences between Angel and VC investments, expanding the concept of entrepreneurship, is running a startup for you?, How To Become A Cybersecurity Entrepreneur In A Crowded Market, and making your elevator pitch more memorable, all that and more on this edition of Startup Security Weekly.

See the special offer from Michael below -- and take a moment to send Michael your answers to these two questions:

  1. What is the most pressing issue you face right now that Straight Talk would help you solve?
  2. What is holding you back?

Interview Questions

  1. What is unique about running a security startup?
  2. How about moving from a services/consulting company to a product company?
  3. What are some unique things investors are interested in when talking to security startups?
  4. Where are the best opportunities in the market for security startups?
  5. What advice do you have for those who may have an idea and want to create a security startup?
  6. What are some of the most exciting security startups in the industry right now and why?
  7. What advice do you have for enterprises looking at solution and considering (or not) a solution for a security startup?

The Five Stories

Key bullet points and discussion items for each story; weaved together in a story arc

Each includes a discussion on the security considerations from each of the perspective(s):

  • Startup
  • Buyer
  • Investor

6 Ways Angels and VCs Think Differently

  • If you decide you can't bootstrap and need funding, it's worth understanding the different types of funding - and what each provides
  • I didn't fully realize #1 - but consider the upside --> emotional detachment and broad experience could be precisely what you need
  • Who's money are they investing, and do they have "skin in the game" -- or emotional attachment; but then question if that's what you seek
  • Explore and match the motivation of an angel to your needs. Can't stress this enough.
  • Consider the value of VCs that work in specific models, regions, or industries (think Shark Tank)

We Need to Expand Our Definition of Entrepreneurship

  • This is a founding tenet of this program: everyone has and benefits from the startup mindset
  • Citing lots of people I like - and predicting the age of an entrepreneurial society; as such, we all must become entrepreneurs
  • In the public mind, entrepreneurs have been reduced to young people who want to create world-changing businesses that can quickly reach $1 billion or more in market value — the fabled unicorns.
  • In a world of accelerating change and growing uncertainty, even the largest companies may need to reframe work.
  • shameless plug: this is what Straight Talk does

20 Things You Should Ask Yourself If You're Wondering If Entrepreneurship Is Right for You

  • We just discussed - and redefined - entrepreneur; but if you want to strike out on your own, should you?
  • Michael: I think everyone should try it... but it's definitely not the right choice for everyone. Sometimes you need to find the right organization that lets you execute with the mindset, but offers you lower risk
  • Question 1, rephrased, is "what problem are you trying to solve?" -- and I'd add --> are people aware of the challenge, are they willing to pay for you to solve it, and can you make a living on that?
  • Question 7 took me a while, and now it's the question that drives a lot of conversation while watching Shark Tank; do you want all of nothing, or a piece of something big? Lifestyle?
  • Question 8 is harder than it seems... and are you willing to ride the emotional roller coaster? How about feeling like a bad parent, sibling, spouse, and friend... as you try to juggle everything else?

How Clever Leaders Overcome More Talented and Better Funded Competitors

  • We recently talked about the importance of passion and why VCs look for passion; it's what carries you forward. Passion is contagious.
  • IOW, their passion crafted a picture of a better tomorrow (as Michael calls it) that inspired others into the effort (a key component of leadership)
  • The difference between someone doing something because they want to and not because they have to is huge.
  • This is a key tenet of Michael's work -- I prefer to explain it as exceptional leaders elevate those around them, accelerate them on the path to success
  • This is also why exceptional leaders never have a shortage of talent and remarkable people to work with

The Cheapest Cities to Base Your Tech Startup

  • You don't have to be in NY, Silicon Valley, Boston, or Austin
  • And this list is not exhaustive, either
  • Perhaps it's a signal that the startup mindset is spreading...

Updates: Our Startup Journeys

Michael - Security Catalyst - @catalyst

Getting ready for Cohort 2 of the Straight Talk Leadership Experience -- starts October 31

  • Open enrollment week of October 24th (limited spots) --> I'll post the link here once it's open

New website updates coming this weekend

  • Adding in "Foundation 5" resource page
  • Updating the Straight Talk Framework resource page
  • Building a 7-step video course on using the Straight Talk Framework

I'm excited to get into a place to share and eager for your feedback. Exploring putting in a "How it works" button to support the effort. Do you see value in that?

Week of sharing next week, including how to handle top challenges:

    • making space to invest in yourself - and how that actually gets you time, clarity, and a host of other benefits
    • how to map value (preview: I'm making the 5 Lenses of Value available this weekend) to training or anything
    • how to make the case using the Straight Talk Framework

I'm also going to start experimenting with ads (Facebook, LinkedIn, and maybe Twitter).


  1. Revealed: The Top 5 Strategies Startups Must Follow To Tighten Up Their Data Security
  2. The Top 10 Branding Mistakes Entrepreneurs Make