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Bootstrapping a Software Product

Garrett Dimon
September 09, 2011

Bootstrapping a Software Product

A rapid-fire presentation about the things that I got right and the things I got miserably wrong while bootstrapping Sifter as a sole founder.

The popularity of this presentation online planted the seed for what eventually became a book going into more detail about the experience: [Starting & Sustaining](https://garrettdimon.com/starting-and-sustaining).

Garrett Dimon

September 09, 2011

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  1. Founder, designer, and developer of Sifter which is a very

    simple hosted bug and issue tracker. Hi, I’m Garrett Dimon
  2. Smallish Ruby on Rails App 2 Web/Application Servers 2 Database

    Servers (Master & Slave) 1 Job Server ~10,000 Active Users ~60 requests per minute ~250 requests per minute at peak About Sifter
  3. These are simple opinions based off of our experiences. Every

    person, team, and application is different. Take it with a grain of salt. There are plenty of successful businesses for which this stuff wouldn’t be true. Disclaimer
  4. Growing the business from profit. (as opposed to outside investment*)

    Bootstrapping We actually started with $16,000. We spent $10,000 on startup costs. We spent the other $6,000 on advertising after launch. Totally possible to do it with less, but the money made it much less stressful. *
  5. Digital stuff that you sell for money.* (as opposed to

    consulting or services) Software Product It should literally make money when you’re asleep. In our case, billing runs nightly and automatically puts money into our account. Services businesses can’t scale exponentially. One person can only do so much work. *
  6. Examples... ★ Icons ★ Templates (Keynote Kung Fu) ★ Mobile

    Apps ★ Desktop Apps ★ Web Apps ★ PDFs or eBooks ★ Screencasts ★ Online Workshops (to some degree)
  7. No Bureaucracy Control Your Destiny Mailbox Money Do Fun Stuff*

    Flexibility* Family Time* Get Rich* Hopes & Dreams
  8. Fears (Excuses?) Health & Disability Insurance Not Enough Money* Not

    Enough Skills* Not Enough Time* Not Enough Experience* No Good Ideas / Crowded Market* Failure*
  9. 1. Getting Ready Start with a little money. Be ready

    to be broke. Anticipate a long journey.
  10. Fear & Excuses Explore. Still on the fence. Prepare. Committed,

    but haven’t shipped. Transition. From part-time to full-time. Work. Answering to paying customers.
  11. 2008 2011 2009 2010 Operating Costs Part-time Salary Full-time Salary

    Pre-Sifter Salary Full-time Quit Job Launch Idea Engaged Wedding Buy House Honeymoon First Child Move Move Again Europe Puppy Most Challenging Time of My Life
  12. Good Decision Didn’t put my life on hold. Got engaged,

    married, bought a house, moved twice, went on a honeymoon, went to Europe, and had a child. Point being that while it’s not easy to make sweeping life changes, it’s certainly not impossible.
  13. Bad Decision Failed to recognize the stress it put on

    my wife. Sifter consumed an incredible amount of attention the first couple of years. Even when I wasn’t working on it, I was thinking about it.
  14. First and foremost, a start-up puts you on an emotional

    roller coaster unlike anything you have ever experienced. You flip rapidly from day-to-day – one where you are euphorically convinced you are going to own the world, to a day in which doom seems only weeks away and you feel completely ruined, and back again. Over and over and over. And I’m talking about what happens to stable entrepreneurs. Marc Andreessen
  15. Bad Decision Focused too much on short- term ups and

    downs. Now, I try not to worry about anything until it’s been a trend for a week. (That’s not to say I ignore it. I just don’t worry about it until it’s a “real” problem.)
  16. Good Decision Looked back every few months at accomplishments. Day-to-day

    it felt like we weren’t getting anywhere, but looking at three months at a time, it was a different story.
  17. Bad Decision Let fraud get the best of me. We

    had it under control. Cost us $200 in fees, but I let it consume me for two weeks.
  18. Good Decision Went all-in and planned for it to be

    more than a side project. With operating costs, $1,000/mo. of revenue is nothing, and running a hosted web app isn’t worth it. It didn’t get “easy” until it supported me full-time and had profit of its own.
  19. Good Decision Got a business partner. He brought more business

    knowledge and took a lot of the operational burden off of me. (Accounting, legal, insurance, etc.) Also, cash.
  20. Good Decision Brought on a technology advisor. Helped with a

    lot of early tech decisions as well as helping us find our current systems administrator.
  21. Bad Decision Didn’t get a tech partner. I’m more of

    a designer first and developer second. Keith is more of a business person. Would have been nice to have someone focused exclusively on tech. Ultimately managed just fine, though.
  22. Good Decision One person has controlling interest and decision making

    responsibilities. At some point, there needs to be a goto person. Mixed messages and blurred visions cause problems.
  23. Bad Decision Lacked confidence in myself. Had our advisor work

    on it part-time instead of taking the leap myself. Early on, nobody was better for the company than I was.
  24. A) Email Integration B) Attachments C) Search D) API E)

    Milestones F) OpenID G) Text Formatting Which of the following features are “must have for launch”? XNone of them
  25. Good Decision Launched early. Sifter didn’t have search, file uploading,

    email integration, API, milestones, or OpenID. We still don’t have text formatting.
  26. Good Decision Didn’t add features as a knee-jerk reaction to

    a request. Often, we’d get one request one day and the exact opposite request the next day.
  27. Good Decision Explained decision-making about including or excluding features to

    customers. Forced us to think things through, and usually elicited good conversation to validate or invalidate an idea.
  28. Good Decision No custom statuses. This one decision defines Sifter.

    This is simultaneously the number one complaint and number one favorite feature. It’s polarizing. Keeping it simple has given us so much flexibility.
  29. Bad Decision Made decisions too quickly. Debating between a couple

    of minutes of downtime vs. 20 minutes of downtime. Making the decision too quickly led to bigger problems.
  30. Good Decision Handled bad situation with complete openness and honesty.

    Made a mistake that led to 8 hours of data loss. Offered credit to all affected customers. Cost us about 10% of that month’s revenue. All customers were understanding and grateful.
  31. Bad Decision Fell into the feature trap. Spent 2 months

    building features that only get used 2.3% of the time. The vocal minority can be very distracting.
  32. Good Decision Used data to guide decisions. Customers ask for

    a feature. I check their account usage, our analytics, and Sifter logs for trends and usually find better solutions.
  33. Good Decision Embraced criticism. If people take the time to

    criticize, it’s because they feel that the product is already pretty solid. If it’s way off, they don’t say anything at all.
  34. Bad Decision Worried about cancellations. Added exit interview to understand

    cancelation reasons. Almost all cancellations are small companies or freelancers that used Sifter for 1 project and the project is over.
  35. Good Decision Take ridiculously good care of customers. I never

    take time off, and it’s rare for a customer to wait more than an hour for a response from support. Always same day.
  36. Bad Decision Obsess about taking care of customers. I would

    stress out if it took me longer than an hour to answer an email. Nobody ever expected hour- turnaround except me. I’m harder on myself than even our most demanding customers.
  37. Good Decision Recognize toxic customers. From time-to-time, customers lie or

    do other shady things. Best to just do whatever it takes to make them happy and move on. Spending time on toxic customers only hurts your other customers.
  38. Bad Decision Let customers put accounts on hold indefinitely. Was

    idealistic and thinking people would go on hold for 2-3 months at a time. 85% never returned. They simply went on hold instead of canceling. We continue to have an obligation, and they don’t.
  39. Good Decision Advertised early. Initial advertising got the word out.

    Subsequent advertising was significantly less effective.
  40. Bad Decision Continued advertising. Ultimately spent almost $10,000 on advertising,

    but only the first $5,000 was truly worth it. Might do some advertising once 2.0 is out, but probably won’t.
  41. Good Decision Wrote. Blogged. Shared. Explained. Built an audience. Validated

    ideas. Forced me to clarify my thinking. Writing and explaining things has a weird way of forcing you to understand something better than you would have otherwise.
  42. Good Decision Didn’t worry about people stealing our ideas. By

    the time they copy what you’re doing, you’ll be on to the next thing. They’ll always be a step behind.
  43. Good Decision Charged money during beta. Not for revenue, but

    to filter people and test the billing system. We charged $5 per month just as a barrier to entry. People will use any piece of crap software if it’s free.
  44. When you have to prove the value of your ideas

    by persuading other people to pay for them, it clears out an awful lot of woolly thinking. Tim O’Reilly
  45. Good Decision Didn’t do free accounts or discounts. People will

    use anything if it’s free. We want people to use it because they like it, not because it’s free. Also, those generally make for the worst customers.
  46. 0 7.50 15.00 22.50 30.00 Average # of Months with

    Sifter Personal Small Medium Large Massive Cheapest plans stay with us the fewest months.
  47. 0% 12.50% 25.00% 37.50% 50.00% % of Each Plan that

    Ultimately Cancels Personal Small Medium Large Massive 45% of all personal plans get cancelled
  48. 0% 10.00% 20.00% 30.00% 40.00% Plans as a % Total

    Revenue Personal Small Medium Large Massive 65% of revenue from $14 and $29 plans
  49. Good Decision Aimed for monthly profitability. And didn’t outgrow our

    revenue. Weren’t afraid to spend money, but tried to make sure that we always ended the month with more money than we started. A yearly budget is key because many significant costs are not monthly and would otherwise be off the radar until it’s too late.
  50. Good Decision Run billing daily. Constant stream of income, and

    billing problems only affect a small portion of customers.
  51. Good Decision Kept personal costs low. No office space. No

    debt. Could have done better, though. You will be your company’s single biggest cost center.
  52. Good Decision Watched financials like a hawk. Kept a close

    eye on our bottom line, cash flow, and money in the bank.
  53. Bad Decision Watched financials too closely. I updated our numbers

    almost daily, and kept too much detail. Weekly is more than enough.
  54. Hosting Performance Monitoring Source Code Management Uptime Monitoring Transactional Email

    DNS Management Exception Management File Storage Transaction Fees SSL Bookkeeping Accounting Legal System Administration Team Software Business Insurance Health Insurance Merchant Account Domains Your Cost of Living Know Your Costs
  55. Good Decision Didn’t open source the application. If it wasn’t

    providing my income, I wouldn’t have made time for it. Would have been too difficult to stay excited about the vision.
  56. Bad Decision Built our own billing system. To our credit,

    we didn’t have much of a choice at the time. These days there are plenty of choices.
  57. Good Decision Bootstrapping forced us to scale cautiously. By letting

    our profits determine how much we invested in the company, we couldn’t spend time on the wrong things.
  58. Researchers found that certain factors – such age and gender

    of founders, location, and previous entrepreneurial experience – have little bearing on a startup’s likelihood of failure. The most consistent predictor of failure, rather, was a startup’s propensity to engage in premature scaling. Startup Genome Project Interviewed 3200 Startups (Quote is really focused on “high-growth” startups.)
  59. Bad Decision Waited too long to go full-time SSL. The

    cost is negligible, and the value is infinite. With web applications, it’s expected these days.
  60. Bad Decision Obsessively worried about downtime. In 3 years, we’ve

    had about 8 hours of unplanned downtime. Only half of that was under our control. I spent 8760 hours worrying about it.
  61. Good Decision Didn’t obsess over automated testing. Building a business,

    not a test suite. Sifter simply wasn’t complicated enough in the beginning and we didn’t know what we were building.
  62. Bad Decision Didn’t obsess over automated testing. We did a

    little, but not much. We’ve definitely had to add it in as we go and as Sifter becomes more complex.
  63. Bad Decision Waited too long to goto a high availability

    hosting environment. The setup isn’t trivial, and the up front costs are significant, but it’s worth it. Easier to scale. More redundant. More insulated from problems. Faster.