Startup Founder: Prepping, Prototyping, and Pitching

In 2 days I’ll be celebrating my 6 month anniversary of leaving my last startup and working on my current one (cue Jay-Z).  Having been a startup engineer I knew I had to prepare myself for the transition to founder.

The long hours of a startup engineer are drastically different from the long hours of a founder.  At least for myself, I spend the entire day context switching instead of coding.  In any given day I meet to pitch to investors, do usability testing, then its onto prototyping and coding, and ending the day thinking about business strategy.

So how does one handle all of this?  Preparation.

Prepping

I spent the first two months brainstorming ideas, reading, and networking.  I spoke to anyone and everyone who would meet with me: investors, users, and founders (even some who were potential competitors).  The reason I did this is because I wanted to understand the problems users were having, how investors evaluated the market I was in, and the approach other founders had taken to address the needs of the first two.

Once I thought I handle on the problem I was trying to solve I transitioned to creating a solution, through paper prototyping.  I ran usability tests with paper prototypes, because I wanted to make sure that what I wanted to build would be a value to them.  I did several iteration of this on a wide audience.

I stuck a fork in the process and decided it was time to build.  Realizing that I couldn’t build everything and also trying to plan for future hires, I broke down the prototype and created a product roadmap.  During the course of this process I thought about what the most compelling feature would be and to me that translated to what was the most pressing user pain point.

Prototyping

Before I wrote a single line of code, I first wrote a formal spec on the first feature that would be released.  This may seem counterintuitive to running fast, but I wanted everyone on my team to be on the same page about what we were building, why we were building it, and then work together on the how.  I included mock ups for the designer, system interactions for developers, and finally suggestions for usability testing.  Then I sat down with each group.  My designer and I talked about simplifying the design – taking away components and streamlining a user’s workflow.  The engineering team and I talked about data modeling, error handling, and how to architect our code base.

Once we released the first iteration of the prototype I had everyone on the team play with it for a couple days and send me feedback on what they saw as show-stopper bugs and any functionality that wasn’t intuitive or user-friendly.

The standard to determine the first iteration’s success was for users to tell us that they wanted to use the product immediately as is.

Pitching

Before I even thought about pitching, I spent sometime understanding the investment market and conditions.  Since my last startup the investor market has changed a lot, and not just because of the recession.  There has been an increased presence of incubators, Angel Investors, and seed funds.  And they are all competing against each other.  There are also a wider variety of investment vehicles to choose from these days: bootstrapping, convertible notes, and seed funding.

The key for me has been to find the right investment vehicle and investor relationship that will get me to my next milestone.  Putting together a business plan helped me evaluate what it is I needed.

The next phase was to pitch.  I’m not going to delve too much more into this:  know your audience and know your business.

The past 6 months have been awesome, while the process has been time consuming its been incredibly engaging!  It’s been a series of coming up with experiments and executing them.  What has been extremely valuable for me has been taking the time in the first couple months to explore, learn, and understand in three market segments: product (existing and tried solutions), user (pain points), and investment.

I’ve seen a lot of startups that just start executing and maybe that works for them, but I guess I’m more of a girl scout :)

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Startup Engineer: Which number is right for you?

Having been an engineer at a startup I empathize with people who are being recruited into startups especially if it’s their first startup. The key deciding factor for me was that I wanted to learn everything about engineering a consumer product. Sure making bank is a nice motivation, but I quit my Masters at Stanford because I knew I’d learn a ton more working on the ground floor of a startup than I would sitting in a classroom. I still wholeheartedly believe that the only way I learn is by doing, which is why I’m starting a company instead of getting an MBA. It’s my MO but that doesn’t mean it works for other people.

The point of this post isn’t how to negotiate or what to ask for because it really depends on your needs (maybe I’ll cover that later). Its meant to paint a realistic picture of what life is like as a ground floor engineer versus past 10, 20 and 30+.

Being a ground floor engineer means you work everyday… 365 days at the very least for the first year. You’re expected to be a generalist, and its best if you’re passionate about the product. There’s just a shit load to do: features, infrastructure, testing, integration, bug fixes, mastering new technologies, bringing others up to speed on the architecture, interviewing candidates, and the list goes on. You’re on call, you fix everything big and small, and you don’t complain you just learn and do! The benefit is you have one of the biggest equity stakes in the company, but the bigger benefit is you know how the entire system is architected and the code you’ve written impacts millions of people! I chose this role for myself because I wanted to be a generalist and learn how the entire system was integrated and built (also why I majored in EE and CS). I also wanted to gain some insight into prototyping and how product’s evolved. If you’re a hungry geek do yourself a favor and don’t settle for anything over 10. Start early!

5-10 stuff is built… but you’re still adding a ton of value to the product and defining the engineering team. You might miss out on a lot of the business and product decisions that were made early on, but if the company is pivoting then it’s ok. You’re still going to play a heavy hand and have your pick of projects long-term.

10-20 this is when startups call in specialists. They are interested in hiring a front-end or back-end developer, algorithms guy, or architect. Not really a hacker-type, but someone who has a deep understanding of a set of technologies or a predilection towards a particular area. Its also one of the more risk averse positions because the startup has mostly likely gone through 1-2 rounds of funding and has gained user traction.

20-30+ get ready to scale and maintain! There’s still a lot of innovation going on, and its focused on scaling the system to support user growth. If you’re a young engineer you’re probably going to be thrust into the maintenance camp, learning the existing architecture first before being given your first juicy project. But hey its a startup and it’s making progress! If the founding engineers are still around you’re in luck because they’ll have a ton of knowledge to impart.

The biggest thing to think about when deciding what stage you want to start at is knowing personally how comfortable you are with change. New people starting every day, week or month, business goals and priorities switching courses, having new bosses, and your own workday context switches: working on a project to fighting fires and back to coding. The earlier you start the more change you deal with and the less time you have to really sit down and think through problems.  You’ve got to be quick on your feet,  and deal with the ebbs and flows – learn to adapt and accept. If you like stability start later.

Regardless of which position you do decide, a startup is a lot of fun, but it’s a lot of work.  It’s not a cushy job nor is it a way to get rich.  Its like buying a home: don’t be fixated on flipping it, picture  yourself living in it for the next 4-7 years because thats how long it will be if it’s going well.  Your teammates are the family you are going to raise in it, and you want to make sure you fit in well with the culture and community.  Most importantly make sure you buy  and believe in the long term vision of the founder.

(I was affectionately called #2 at Mint.com, because in the words of Aaron Patzer, “…engineers start counting at 0.” )

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Major bug or vocal minority?

My recent blog post for Seattle 2.0: Major bug or vocal minority?  How to Use Feedback from Product Users.  The post covers how to think and evaluate bugs and features in the context of  pleasing users.  I’ll also be speaking at Deploy 2010, hosted by Seattle 2.0.

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Self-Direction Leads to Your Calling

From the ripe age of 8 I’ve been thinking about my career, I aspired to be a lawyer, professor, and writer.  I read all the time and wrote stories for fun.  I had lofty goals of being published in seventh grade, but my dreams were curtailed when my family moved.   I can’t say it was all self-imposed because a large part of it came from having immigrant parents who really valued education and instilled a hard work ethic in me.  My mom for several years worked and went to school, and my dad never ceased to be reading a book on business or engineering.  The both of them spent a lot of time with my brother and I while we were in grade school.  In high school I rebelled, and didn’t want them spoon feeding me.  I often wouldn’t show my parents my report card or tell them what classes I was taking.  I just wanted to have time to explore.  I was studious enough that they backed off.  To me it was more important to have the freedom to be self-directed.

I joined the debate team because I wanted to be a lawyer, and figured I had to be really good at public speaking.  I also  learned Spanish because I wanted to be able to work with a wider variety of people and travel for work.  In college I TA’ed every year because I wanted to be a professor.  I made all these choices on my own, but I think they came from my parents instilling the value of caring about one’s path in life, and finding purpose.  They also instilled a healthy fear of mediocrity in myself and my brother.

Whenever I meet recent graduate from high school, college, and even HBS many of them don’t seem to know what they want.  It’s ok to not know so long as you’re moving in a direction of discovery.  They ask me for advice on majoring in engineering or being an entrepreneur; two careers that I never imagined pursuing but have naturally gravitated towards.  My response has always been to spend time thinking about what you like doing best, for me it’s reading, writing, coding, and speaking.   But there’s a bigger issue here, a lot of people don’t know what they are good at or enjoy doing.  They struggle with the part of just getting good at something.  The first step is discipline.  Pick just one thing to be disciplined about, and realize that you’re not always going to love doing it.  You start to love it as you build confidence, and the way to build confidence is to learn, practice, and refine.  In high school I primarily focused on debate, and in college it was engineering.  I spent 4 years in high school doing public speaking.  Everyday was spent practicing, thinking, and presenting in front of a variety of audience.  And I’ve spent the last 10 years learning, reading, and coding in order to become a better engineer.

Being self-directed implies having a plan of action, not one that is set in stone, but one that is focused on being good at the current job or interest.  This helps you focus on acquiring skills and experiences.  To me skills are just tools that you use to execute everyday, you learn from experiences and they give you the opportunity to hone your skills.  The combination of the two leads you to your ultimate goal of finding your calling.  But the biggest component is wanting to explore on your own, and picking a direction and sticking to it until you are no longer learning and improving.

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Perspective on Pitching

Having been at the ground floor of a startup before I’ve experienced writing the first lines of code, shipping a product, and then getting acquired, but I never had the experience of pitching or seeing someone else do.  Last Wednesday I did my first pitch for my startup, BizeeBee, in front of about 75 people, a panel of 4 angel investors, and alongside 7 other founders.  While this might seem nerve-wrecking to most, it was an experience I had been looking forward to for months.  I finally felt like a founder!  The event was sponsored by DukeGEN and limited to founders from Duke.

The reason I really liked this format was that before the founders presented the Angels took the time to tell us what they were looking for.  Each pitch last 6 minutes and there was a 3 minute Q&A period following each founders pitch.  Before announcing the winners,  the Angels spent time giving each business feedback, which I found to be extremely valuable because I got to experience first hand how they evaluate and think about business ideas.

Here’s what the angel’s were looking for:

  1. Getting to the heart of the product and what problem it is solving
  2. Large market
  3. Explanation of Customer Acquisition strategy
  4. Team: strong technical and business members
  5. Polished presentation and understanding of each component of your business

Here’s what the Angels focused on during the QA and it making their final decisions:

  1. Many of them questioned the actual market size, and drilled into the numbers presented.
  2. How robust the technology was compared to competitors, and if it was enough of a differentiator.
  3. How much of the product had already been built out.  Having an actual prototype versus a PowerPoint presentation was more powerful.
  4. How capable the founding team was of executing on the business and technical side.
  5. Traction and having customers that were using the product.
  6. The methods used for attracting customers.  Angels really care about your distribution model.

I came in third place.  Here’s the feedback I personally received (yes I’m still leaving my readers in the dark about my product):

  1. Great team, brand, UI, and simple product proposal.
  2. Given that I’m targeting the SMB space, they were concerned about how scalable my business model is given how fragmented of a space I’m operating in.
  3. They did emphasize the need for a couple more key hires such as a VP of Engineering and VP of Sales.
  4. Traction – they’d like to see the customer feedback, how the product and brand awareness will spread, and if I’ll be able to start making money off of customers.

One final note, I want to thank my teammates Liz and John for all their support and hard work that went into helping me prepare the prototype and the pitch!  I couldn’t have done it without either of them :)

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Deploy 2010: 3′S to a Successful Launch

I’ll be speaking at Deploy hosted by Seattle 2.0 on June 24th, 2010.  Building upon a couple of my blog posts (Pre-Launch and Post-Launch) I will be speaking on the engineering execution for a successful Launch.  Here is an outline of the topics I will cover.

1. Stability

  • Security: store and retrieve hashed password, encrypt sensitive information, field validation through JS, Ruby, Java, and DB constraints
  • Bugs: prioritize mission critical vs. look and feel
  • Background Processes: nightly cron jobs, data imports
  • Browser Interoperability Issues: IE Hacks, Litmus

2. Scale

  • Identify bottlenecks through performance testing: JMeter, New Relic, profilers
  • Front-End Optimizations: JS compression, sprite images, measure page load and rendering times
  • Back-End Optimizations: index database tables, avoid costly joins, identify “growth tables”, lazy loading and load fewer columns, caching, process data via db instead of loading into business logic
  • User Experience: design around slow processes

3. Support

  • Logging
  • Error Messages and Error Handling
  • Debugging Tools: scripts for redundant queries, DB admin

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I Don’t Know to CEO: Transforming Passion in Action

On Saturday May 1, 2010, I will speaking on a panel entitled: “Taking Flight – Launching a Belief into a Brand” at the I Don’t Know to CEO: Transforming Passion into Action conference at the Annenburg Auditorium at Stanford University.

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Social Developers Summit

I will speaking at the Social Developer Summit on June 29, 2010 (9:30-10:20am).  The session will be about Scaling Social Analytics.  I’ll cover some of the data analytics I worked on at Mint.com, and propose suggestions for building analytics in from the start to then help with scale.

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Team Dynamics

For the past three months, as a startup founder, I have been focused on customer development, creating a product roadmap, understanding the complexities of the industry of my product, and establishing a company culture.  This month in particular I’ve added another component to the mix: team dynamics. To me team dynamics goes beyond culture fit.  Culture fit is just a sliver, and is tantamount to does this candidate have a personality type that jives with the rest of the members of the team, and they’re willing to be collaborative, basically guaranteeing long-term harmony on the team.  Team dynamics are much more nuanced, and starts with each individual:

  1. Understand the needs of each individual: what are their motivations, and goals both long-term (years) and short-term (day-to-day and months).
  2. Analyze their aptitude: this is based on what they have demonstrated a proficiency in over the past several years, and what they are capable of doing.
  3. Gauge their results: this comes down to giving them a small project, with clearly defined goals and parameters, and a predictable and measurable set of results.  Once you’ve done this walk away, don’t micromanage!

It’s not enough to do this once, you have to do it daily, weekly, and monthly.  The next step is to piece the team together.  Building a founding team comes down to the following:

  1. Complementary skill sets – you want to make sure that people on the team aren’t stepping on each others toes.  Each founding team member should have ownership of what they are doing from the beginning and understand how they are interfacing with one another.  As the team grows owners might change and increase or initial members may want to move onto other projects, which is fine and to be expected.
  2. Communication and comfort – as the founder it is your responsibility to let each member of the founding team know where you are going.  Even people in a startups crave stability, and one of the ways of giving them stability is by giving them a sense of where you are headed over the course of the next week and months.  Its also really important to attend to their most basic needs: food, water, and shelter.  You can’t expect people to work in a stressful environment without compensation!
  3. Shared vision – before someone becomes an official member of your team you want to make sure they are vested into the direction of the company and share the same values and grand vision as you do.  This is a function of you as the founder executing on that mission, and if your direction does change, alert your team of that as soon as your decision is made, or involve them in the decision-making process.

My team is obviously very important to me, and I think about each person individually, and how they fit together.  The reason its important to go through this set of criteria and process is because the founding team you build translates to high performance in both good and bad times, the sort of people they will in turn attract to build out the company, and their decision-making process that will affect the course of your startup’s future and success.

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Deploy 2010

I will be speaking at Deploy 2010 hosted by Seattle 2.0 on Thursday June 24th at Bell Harbor Conference Center in Seattle, WA.  The focus of my talk is pre-launch planning for startups, geared towards engineering.  I aim to cover technologies to use, best practices, and trade-offs to make before crunchtime!

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