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How to be a Startup CTO:
Lessons learned from my 2 startups




  Ryan Hubbard
Who Am I?
• I am You!
     Add 5 years, a little luck & lot of late nights


• 2 Startups – Bootstrapped
     eVariant – MyHealthConnect.com
     YellowHammer Media




@hubmo                                  2
Disclaimer

    Take what I say with a grain of salt




@hubmo                3
What is a CTO?

    is an executive-level position …
    whose … is focused on scientific and
    technological issues within an
    organization


@hubmo              4
What is a Startup CTO?
    Chief Hat Wearer

•   Bringing a vision to reality
•   Bridge between Sales/Marketing & Technology
•   Support Business Operations
•   Sales (Sales Engineer)
•   Last Line of Defense
    o Unrealistic features
    o Downtime
• …..

@hubmo                       5
If You Build It …
         They Will NOT Come!

• You can have the best product but no one knows

• Sales & Marketing are more important

• Bridge the gap btw Biz & Tech – Attend Sales Calls!



@hubmo                     6
Supporting Biz Operations
• You’re the most logical, so help w/ process

• Help Company Select the right Software
    o    CRM
    o    eSigning
    o    Project Management
    o    Email Marketing
    o    Stay on Top of what others are using

• Empower those users
    o Don’t get stuck always doing everything (admin, customizations, etc)




@hubmo                                   7
Software
CRM          Email Marketing    eSigning         PM


Salesforce   MailChimp          EchoSign         Asana



HighRise     Campaign Monitor   RightSignature   Pivotal Tracker


Capsule                         DocuSign




@hubmo                           8
Build It Fast
• Tech wants to build a castle – Keep it simple
    o Property architecture, scale, etc

• Biz cannot advance w/o product
    o Product can live w/o scale

• 80/20 Rule

• Don’t build what you think you need in 6 months

• You can buy more servers, harder to buy good codebase


@hubmo                                    9
…Build It Smart
• Cloud Hosting
    o    AWS, RackSpace, Heroku

• New Technologies
    o    BigData – Vertica
    o    NewSQL – VoltDB, Akiban, MemSQL
    o    Searching – ElastiSearch
    o    Web Servers – Node.js

• Don’t be afraid to migrate tech early

• Hybrid Architecture
    o    Backend - Node.js / Rails
    o    Database - VoltDB, Vertica

• Look for the right way
    o    Don’t implement it poorly just cause that’s how you know how to do it



@hubmo                                              10
Decision Making
• Use a Point System
    o Positive & Negative points
    o Apply to everything


• Don’t Procrastinate
    o Unless its about a feature you think you need in 6 months




@hubmo                              11
Tech & Dev Ops
• Monitoring
    o CloudWatch, Nagios, Applications Manager


• QA / Unit Testing
    o TDD, BDD


• Deployment / CI Server
    o Capistrano, Jenkins, TeamCity




@hubmo                                12
Always Be Hiring
• Blog
    o Business & Tech


• Open Source Projects
    o Combover


• Recruiting Events
    o NYC Uncubed, Talent Fairs, Local Colleges


• Network, Network, Network
    o Meetups, conferences

@hubmo                             13
Thanks!

         Ryan Hubbard
         @hubmo




@hubmo                  14

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How to be a Startup CTO

  • 1. How to be a Startup CTO: Lessons learned from my 2 startups Ryan Hubbard
  • 2. Who Am I? • I am You!  Add 5 years, a little luck & lot of late nights • 2 Startups – Bootstrapped  eVariant – MyHealthConnect.com  YellowHammer Media @hubmo 2
  • 3. Disclaimer Take what I say with a grain of salt @hubmo 3
  • 4. What is a CTO? is an executive-level position … whose … is focused on scientific and technological issues within an organization @hubmo 4
  • 5. What is a Startup CTO? Chief Hat Wearer • Bringing a vision to reality • Bridge between Sales/Marketing & Technology • Support Business Operations • Sales (Sales Engineer) • Last Line of Defense o Unrealistic features o Downtime • ….. @hubmo 5
  • 6. If You Build It … They Will NOT Come! • You can have the best product but no one knows • Sales & Marketing are more important • Bridge the gap btw Biz & Tech – Attend Sales Calls! @hubmo 6
  • 7. Supporting Biz Operations • You’re the most logical, so help w/ process • Help Company Select the right Software o CRM o eSigning o Project Management o Email Marketing o Stay on Top of what others are using • Empower those users o Don’t get stuck always doing everything (admin, customizations, etc) @hubmo 7
  • 8. Software CRM Email Marketing eSigning PM Salesforce MailChimp EchoSign Asana HighRise Campaign Monitor RightSignature Pivotal Tracker Capsule DocuSign @hubmo 8
  • 9. Build It Fast • Tech wants to build a castle – Keep it simple o Property architecture, scale, etc • Biz cannot advance w/o product o Product can live w/o scale • 80/20 Rule • Don’t build what you think you need in 6 months • You can buy more servers, harder to buy good codebase @hubmo 9
  • 10. …Build It Smart • Cloud Hosting o AWS, RackSpace, Heroku • New Technologies o BigData – Vertica o NewSQL – VoltDB, Akiban, MemSQL o Searching – ElastiSearch o Web Servers – Node.js • Don’t be afraid to migrate tech early • Hybrid Architecture o Backend - Node.js / Rails o Database - VoltDB, Vertica • Look for the right way o Don’t implement it poorly just cause that’s how you know how to do it @hubmo 10
  • 11. Decision Making • Use a Point System o Positive & Negative points o Apply to everything • Don’t Procrastinate o Unless its about a feature you think you need in 6 months @hubmo 11
  • 12. Tech & Dev Ops • Monitoring o CloudWatch, Nagios, Applications Manager • QA / Unit Testing o TDD, BDD • Deployment / CI Server o Capistrano, Jenkins, TeamCity @hubmo 12
  • 13. Always Be Hiring • Blog o Business & Tech • Open Source Projects o Combover • Recruiting Events o NYC Uncubed, Talent Fairs, Local Colleges • Network, Network, Network o Meetups, conferences @hubmo 13
  • 14. Thanks! Ryan Hubbard @hubmo @hubmo 14