AMA: Co-founding CTO at a Silicon Valley startup

TravelBank zysP52
Feb 6 264 Comments

I am a co-founder and CTO at a travel and expense management company in Silicon Valley with more than a decade of experience in systems architecture and software design and development.

Previously, I ran my own consultancy in D.C. and worked for a company to build a social media monitoring tool that was key in the Microsoft acquisition of my employer.

I also served in the Marines as both a network/systems administrator and a developer.

Ask me about:
* Co-founding a company as a CTO
* What my military experience taught me about tech and business
* The difference between building and operating effectively for mobile vs. desktop
* Team building and leadership
* Our open positions ;)
--
EDIT: 2/6 @ 9:41pm - Thanks for all the comments and questions, I really enjoyed them. I'll be signing off for now and checking back in the morning to see if there are any other questions I can answer.

comments

Want to comment? LOG IN or SIGN UP
TOP 264 Comments
  • SAP vQHt1V
    What are some learning experiences from your consultancy that shaped your startup?
    Feb 6 1
    • TravelBank zysP52
      OP
      One of the biggest things that helps me today is the ability to get in front of a client/stakeholder/customer/fellow executive, and determine the best way to translate what they need from a business and values perspective into a technology based solution. I mean this in a few ways:

      * You ultimately need to build something that solves a problem for your client (head's up: this is the same for a startup - except it's your customer), so you'll need to understand the pain points they have and how to build a solution that works towards that.
      * Secondly, it takes a lot to be able to bridge the technology/business barrier in communication. Those two areas of the business can sometimes be conflicting, and I draw on that consultant experience to make sure I can advocate for the business, as well as the technology, and ultimately find a balance that works for both.
      Feb 6
  • Amazon VTYFPs
    I'm a relatively new grad who wants to start her own company eventually -- best way to learn and acquire skills at a large established company or startup?
    Feb 6 3
    • Uber LovR
      If you join a startup you can get a first-hand experience of how that startup operates on a macro and micro-level. I have worked in over 10 startups and now that I joined a big company (with over 30k employees) I am getting first-hand feel for how to create a big architecture system handling multiple apps, tools, processes and contributions by hundreds/thousands of employees. Having the former experience is good to get started with an idea (business plan is very important!! Functional requirements and funding are next in line). Having the latter experience is good for keeping your position as CEO in your company and you'll know how to grow a small startup into a medium and large company hopefully without being overthrown. Of course you will most likely hire coaches or take personal advice from investors, etc but you can plan your entire org architecture for growth and not reorg. Reorg is not necessarily needed if you can avoid it - but most companies/CEOs don't account for all the changes and think "redo" or "make over" when the time is ripe for change. You can change buildings and hire more people but no need to make a big overhaul for adjusting to the new changes if your system is already designed to handle growth. I'd say, join a few startups first then a big company (or 2) for more learning and growth and finally move onto your own startup....at least that's the plan I laid out for myself and following it to the dot 😉
      Feb 6
    • TravelBank zysP52
      OP
      I love this feedback, @LovR
      Feb 6
  • Amazon 2HAHoW
    How hard is it to find great engineers that want to work for a startup?
    Feb 6 1
    • TravelBank zysP52
      OP
      Similar to my earlier response, hiring great people was a hard lesson that I learned early on. It's quite difficult to get someone to take a bet on your startup in the early stages, but fortunately, we've been able to build a great team with an environment and culture to match over time.
      Feb 6
  • Microsoft XXMM50
    Do you smoke weed?
    Feb 6 6
    • Airbnb wise taco
      Concur sucks so hard, I don't understand why anyone still uses it
      Feb 6
    • Cisco hj5865
      ^this x1,000
      Feb 6
  • Airbnb wise taco
    You're a series A startup offering 0.02-0.05% equity. If your company sells or IPOs for 1B, assuming no additional dillution, that'd yield 200k to 500k for 4 years of work. Dividing by 4 that's 50k to 125k / year.
    I understand the inability to pay a high base or a high bonus, but what's the reason for such low option amount?
    Feb 6 9
    • Airbnb wise taco
      Yeah offering a lower base to avoid shortening the company's runaway is fine, but offering low stock or even trying to anchor it and negotiate shows a very "I don't care about you" attitude. It's praying on people that don't know how options work and naively believe they have a lottery ticket, when what they actually have is a raffle ticket.
      Feb 7
    • Leia wVbm32
      This is a holistically poor strategy @OP. This is the reason startups like yours fail to retain good talent.
      Feb 9
  • Argo AI Arrrrgo
    Can you hurry up and replace concur?
    Feb 6 0
  • Google abczzz
    How hard is it to hire people?
    Feb 6 4
    • TravelBank zysP52
      OP
      We've hired in SF and in remote. Luckily, we've had very little turnover at our company - and I attribute that to the culture that we've built.
      Feb 6
    • Deloitte tpMT46
      Better question, why not find a capable engineer on this board that’s willing to work remote
      Feb 6
  • New / Eng fyou.js
    What is the story of the software? Tech stack in mvp stages into growth and at scale? Did you build the product or outsource? You didn't really give any base info about the tech side of your biz, you just shared some accomplishments and left out the TC and revenue #s
    Feb 6 7
    • Google / Eng swe#
      Thanks for the responses by the way
      Feb 6
    • TravelBank zysP52
      OP
      Our originally MVP took about 6-8 months, with me as a lead engineer and working with and managing some great offshore engineering talent. Our product has changed so much since that first period of time, and I think that you don't know what you don't know going in, so you'll hardly ever be able to nail the requirements the first time around. Thank you for the great questions!
      Feb 6
  • Capital One anidiot
    How do you get developers in SF to join offering 125-165k for a Lead Full Stack Engineer position? (According to your Angel.co page)
    Feb 6 2
    • He didn't start this. It's a paid sponsprship. The CEO has been shilling this on LinkedIn non-stop. It's an AMA series.
      Feb 6
    • By hiring people without computer science degrees
      Feb 6
  • TripActions Xhgy27
    Curious to know what you feel about us.
    Feb 6 2
    • TravelBank zysP52
      OP
      Hi, and welcome :). Good question, and glad you asked.

      I think that you all are doing great things, and applaud you for that. I appreciate the competition, since a lack of competition can often signal a weak market. Not to mention; considering the market for business travel is $1.7 *trillion* globally, there is certainly enough room for everyone to carve out their own successes, in their own way.

      That being said, we do seem to have some differences, certainly in terms of culture and mindset. Whereas ya'll seem to have taken the mentality of growth at all costs, we're looking to be appropriately aggressive to build a long term and sustainable business that works, for the organization *and* the employees who empower it.

      I look forward to continuing to compete.
      Feb 6
    • TripActions Xhgy27
      Thanks for the honest opinion! See you on the battlefield :)
      Feb 8

Salary
Comparison

    Real time salary information from verified employees