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My Single Founder Y Combinator Experience | Bookmark


It all began on the evening of April 11, 2016, when an email from Y Combinator titled, “Your Y Combinator Application” dropped into my inbox.

An overwhelming thrill immediately came upon me, and I high-fived my wife and called my brother. Being a single founder, the odds were already stacked against me. Many investors find the risks too high with single founders (in particular the risk of burnout) and prefer to invest in companies that have a technical and product founding team. I knew about these odds, so to counteract them, I prepared a demo video showing Bookmark in action:

I have a very strong feeling that this demo video was impressive enough in showcasing our product that Y Combinator wanted to know how a single founder had created something like this, and that’s why they decided to give me the interview.

Every applicant is also asked to provide a Founder Intro video. Here’s mine:

There were 7 days of interviews, with 500+ slots to choose from. I wasn’t in a rush to select my interview spot as I thought I had lots of time. The next morning—to my surprise—75% of the slots were already taken, so I selected my interview time: Tuesday, April 19 at 2:30PM Pacific –day 2 of this batch of interviews. More than 500 interview slots may sound like a lot, but keep in mind that there were 6000+ applications split between the fellowship program and the main program.

The summer 2016 batch was our first ever application to Y Combinator for Bookmark, and we wanted to be prepared. The research began on how to make the most of my interview so we could get into the most famous accelerator program in the world—one that everyone wants to be a part of.

Bookmark is an entrepreneurial platform that is centered on our drag and drop website publishing technology. We have in depth e-Learning courses and a community to help entrepreneurs be successful.  Y Combinator has already accepted other website building companies in the program: Weebly (2007) and Strikingly (2013). My initial thoughts were mixed: on one hand, YC obviously likes the sector, having invested in two companies within it; on the other hand, perhaps their bets were already placed on this sector with their previous selections, making the chances of them investing in Bookmark slim.

However, I didn’t let my worries affect me at all as the focus was to do the best that I could and be prepared for every question. Whatever else happened I would consider it a learning experience. Keep in mind, Bookmark hadn’t launched to the public yet at the time of this interview.

The prep work

Being that I was dealing with the most famous accelerator in the world, I had plenty of resources and articles I could research. I personally read many forums in Quora to learn as much as I could from the experiences (both positive and negative) that other start-ups went through. Whenever I came across examples of questions that I might be asked in the interview, I wrote them down.

I prepared detailed answers to about 50 questions. I made sure I had an answer to each one and had my delivery perfected. Here’s a sample so you can get an idea of how much preparation I did:

What are you working on?

Bookmark is an entrepreneurial platform that is centered on our drag and drop website publishing technology. We have in depth e-Learning course and community to help entrepreneurs be successful.

Who uses your product?

Our target market is small business owners. There are 15.8 million SMBs with between 1 and 19 employees. Bookmark has consultants, wedding planners, photographers, dentists, and trades people—to name a few—using the product.

Why do people need your product?

Forty percent of businesses in developed countries have no web presence. Many others that do are stuck using a product that makes it necessary to hire a technical person to maintain their website. Bookmark is needed as a simple tool that any non-technical business owner can use to manage their website and business online themselves.

Why is now the right time for this product to exist? (Rather than 10 years ago or 10 years from now)

Business owners realize they must have a website in today’s business landscape. Also, they cannot just create a website and expect business to come automatically—they have to learn how to thrive online to grow their company.

How is your product different?

Bookmark is an entrepreneurial platform. We are not only a highly effective website builder, but we offer e-learning courses, analytics, dashboard with notes, to-do lists, and our Ask an Expert community all to support small business owners creating websites with Bookmark.

How are you going to make money?

We are going to charge a monthly membership for people to create a website with Bookmark. We will also sell tools and services that small business owners would need to run an online business, such as email, domains, ssl, stock photography, scheduling, email marketing, support software, and more.

How big can this get?

Shopify is currently valued at $2.4 billion (as of the interview in 2016). Wix is valued at just under a billion (as of the interview in 2016). I feel that there is plenty of room for a solid entrepreneur platform in the rapidly growing market of servicing small business owners.

How will you grow?

I have two channels for acquiring customers at Bookmark: Paid and Free.

We are putting a lot of focus into viral and referral marketing:

1)  Referral Program

We have created a well-thought-out referral program with many features, offering 1 month free to anyone who refers a customer and 1 month free to the person accepting the referral.

2)  Powerful Freemium Model (with branded advertising)

Bookmark offers a free model to all customers—without a credit card. Free users will use a subdomain of Bookmark (e.g. to create their free website. These websites will have an advertising bar in the footer area stating, “Like this website? Create your own FREE at Bookmark.” Clicking on the footer takes you to the sign-up page.

3)  Bookmark Blog

We have started content marketing with social media accounts for Twitter and Facebook, as well as our own blog.

4) Ad buys

We have already started a/b testing over the past 6 weeks on our landing page, with 4 tests currently running and new ones ready to start once we have results. I have broken down our potential customer market into 8 segments differentiated by sex, age, and interests. We will be doing careful ad buys while analyzing our traffic continually through tools such as Kiss Metrics to pinpoint the most valuable traffic and customer segments.

What makes new users try you?

We currently register 10-15 free accounts per day that sign up at Users try us because we have a lot to offer them. Not only can they build a beautiful website, but they can also learn something new about how to help their business succeed. We have built a great community that helps out, and with our free model that allows users to sign up and try out the courses and build a website on a subdomain, they have nothing to lose.

What’s the worst thing that has happened?

The worst thing that has happened is launching into beta too early with too many bugs and wasting an opportunity to interact with customers, as the product wasn’t ready enough.

What’s an impressive thing you have done?

The most impressive thing I have done is build my last company from my parents’ basement to a 55 person company and totaling $60 million in revenue in less than a decade.

Why did you pick this idea to work on?

I started my first company in 1999 and became successful at a young age. Over a 16-year period, I was asked many questions from fellow SMBs: how to start your own website and how to get traffic to it, accept payments, and how to get listed on Google, to name a few. Building this project allows me to give everyone who asks me a complete solution to their needs. I feel there is a need for not only a website creation tool, but a tool that helps explain the steps to take to succeed after you have your website. That’s Bookmark.

Why do the reluctant users hold back?

Bookmark is a new product. Trust is a factor, especially when it comes to the security of your website, hosting, and reliability to be there for the long haul. Users need to invest a lot of time to create their website. They don’t want to lose it if this new company disappears.

Who would you hire or how would you add to your team?

The funding raised in this round will be used to make key hires related to our marketing and sales goals, including: a Chief Marketing Officer, SEO Manager, Community Manager, Partnership Manager, Support Staff, Content/Social Media Writer, as well as the additional development staff needed for growth. The remaining funds will go into marketing to drive revenue and growth.

What problems/hurdles are you anticipating?

I’m anticipating hurdles with users that will not trust Bookmark, users that will find more bugs in Bookmark or will not be able to use the site as we intend, or whose learning curve will be longer than we anticipate.

What is the next step with the product evolution?

We will continue to make the product as user-friendly as possible. I would like to set up more one-on-one sessions with users to get feedback and view how they actually use the website builder. We will add more templates, as we have 7 already designed and are implementing e-commerce and a more advanced Focus feature.

What obstacles will you face and how will you overcome them?

I need to now go after growth and show traction. This will be done by breaking down our target market into many, many different smaller campaigns. I will carefully test each segment to find the target market that resonates best with the product.

Who needs what you’re making?

The small business owner with 1-19 employees would receive the most benefit from our offering.  The DIY type of owner who doesn’t want to leave their company website in the hands of a technical person, making it expensive and complicated to update their website, is our target.

What do you understand that others don’t?

We understand that there is a need in the market for a true entrepreneurial platform that allows a small business owner to DIY, easily be able to update their websites, and have all the tools centralized in one space. We also understand that entrepreneurs need to be educated; they need to learn the tips and tricks to creating a successful company online.

Six months from now, what’s going to be your biggest problem?

I believe that our biggest problems will be keeping the product stable and working as we scale up usage of the product.

What’s the funniest thing that has happened to you?

Well, I took the development team out for a weekend getaway as a thank you for their hard work. The team are eastern European and enjoy drinking Rakia, a national hard liquor drink similar to rye or whisky. The Saturday night we went out was the worst I have ever been sick. The next day everyone was up and out heading to the beach while I spent the entire day in bed.

Tell us something surprising you have done?

I’ve invested $800,000 of my own funds into this project and 20 months of my life.

Who are your competitors?

Wix, Weebly, Squarespace, WordPress, Shopify, Jimdo, Websitebuilder

What’s new about what you make?

We’ve created the only entrepreneur platform for website builders.  We have combined all the tools needed for a small business owner to have a one-stop shop for all their online business needs.

Why isn’t someone already doing this?

Other website builders have a blog, or have a forum for support, but no one has combined everything to create a unique platform like Bookmark.

What are the top things users want?

Users want a website that is simple to build, that looks beautiful, and that is easily updated. They want to feel secure that their website will always be there.

What is your burn rate?

We are burning roughly $15,000 USD a month.

What’s the conversion rate?

Our current conversion rate is 1:25 sessions to Bookmark’s home page. Bookmark, because of its domain name, gets lots of direct type-ins from people likely trying to access their browser’s bookmark list. So I feel that this ratio will be closer to 1:10-1:15 with targeted traffic.

Who would use your product?

Entrepreneurs, solopreneurs, small businesses with 1-19 employees, and the 15.8M potential customers in this segment in the developed countries alone would use our product.

How are you understanding customer needs?

We have set up close communication with our users through feedback loops and our application, which allows us to chat in real time with our users. We also have one-on-one meetings, which we offer to users in different stages of their onboarding and also during cancel process. Last, we have implemented various surveys with 1-5 questions targeted at various stages of customers.

What do you know about this space/product others don’t know?

I feel that we know that a customer is not only wanting a tool to build a website, but they want interaction and ability to communicate with like-minded people and learn new things to help their business. I also feel that our website builder is a perfect blend between structure and customization and usability. Beginner users can create a website quickly and easily while more advanced users can future customize their site to be as they dream.

How much money could you make per year?

I feel we could reach $50,000-100,000 in revenue by the end of year 1. With additional funding, we could then accelerate growth and become profitable in year 2.

Are you open to changing your idea?

Yes, I am open to pivoting in whatever direction makes the company a success.

How do we know your team will stick together?

Three out of five of the team members have been with Bookmark for 2 years.  And the other two are 1 year each.  There is no turnover; the team is excited about the project and its success.

Interview Day

I had flown into San Francisco the day before so that I could be fresh for Interview day. The day started off the way the night before ended, by reviewing each of the questions and answers. The goal was to be able to clearly, confidently demonstrate that our team was well prepared and in charge of any situation and to demonstrate that we will succeed.

Lying in bed with my laptop and headphones on to drown out any other noise within the Airbnb room I was renting did the trick. Another guest in the house was also attending a Y Combinator interview: Andrew Michael from Ads Vise, who had traveled all the way from Cyprus. To make the coincidence even more surprising, his interview time slot was the very next one after mine!  More than 500 interviews and I happen to rent the same Airbnb room in a house together with the very next guy.

We didn’t help each other prepare, as I felt that everyone has their own style and opinions on how to proceed with the interview. I didn’t want to be swayed by his style and get sidetracked on who I am. I wanted to be myself and I’m glad I did it that way because I feel I killed it in the interview.

Actual Interview (my 10 minutes with Y Combinator)

*Shake hands, all smiles and welcomes* I felt at ease, they were human.

Paul Buchheit and Kat Manalac were who I interviewed with.   Paul asked 75% of the questions.  Both were very friendly and approachable. Here are some of the questions they asked:

YC: Hello, so what are you working on?

YC:  How do you know if anyone cares or has time for e-Learning?

YC:  Can’t any of the large companies pivot into e-Learning as a value add to their product line?

YC:  What makes you better than Squarespace, Weebly or Wix?

YC:  How will you grow?

YC:  Who is on your team?  How many developers?

YC:  How did you get the domain, how much did it cost you?

YC:  Who uses your product?

YC:  Why did you pick this idea to work on?

YC:  Well that’s 12 minutes. Wow does time fly.  Thank you for coming in.

The fastest 12 minutes of my life went by in a flash. Apparently there is a knock at the door at the 10 minutes point to let the interviewers know that time is up, but I didn’t hear a thing. I was completely zoned in and on a roll.

I got out of the interview with a huge sigh of relief. I nailed the interview, I thought. I felt so confident that I did well that I was beaming from ear to ear. I saw Andrew, who was up next, in deep thought, so I gave him a high five and let him be. I know how I felt just 12 minutes prior, I was pacing up and down going over the questions in my head and was in a trance.

Waiting for the decision

Eventually the initial high waned and I came back down to reality. I realized I wasn’t in yet: a good interview doesn’t mean that you will be selected, and so the time started to slow again. It was only 3:30 pm. It’s a wait of 3-4 more hours before I’ll get an email or a phone call. An email signified you didn’t get in and a phone call, which is what everyone wanted, was to welcome you to the S2016 batch. The wait dragged on….

At little after 7:30pm I got the dreaded email that Bookmark was not accepted to the program.

The Takeaway

Although Bookmark didn’t get accepted and that was heartbreaking for the next 48 hours, I really do feel that it’s an accomplishment and an honour to be selected to be interviewed among the thousands of other companies.

The preparation that was done for the interview went a long way in the following months as we continued pushing with the launch of Bookmark on Product Hunt, and going into a fundraising round in June. It really helped to focus on Bookmark’s core offering and nail down our goals and next steps.

We’ll try again to apply to Y Combinator, because I’m still convinced that their mentoring program is invaluable. Our next attempt will come when we have a product on the market, with a real user-base establishing traction and the ever-coveted product market fit.

Bookmark Website Builder

Website Comments

  1. Avatar Lisarna Wynyard

    Thanks for the great article Dave. I so impressed to see that Y Combinatior gave you an interview despite your “Single Founder” status. Great motivation for all the rest of us solo founders out there. Good luck with Bookmarks.

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