Jason Shah

Oct 8

Explore and Practice Your Craft

“Experts who acknowledge the full extent of their ignorance may expect to be replaced by more confident competitors who are better able to gain the trust of clients.” - Daniel Kahneman, Thinking, Fast and Slow

It’s scary to think of oneself as an expert. It often requires you to hide your doubts. Doubts. Those doubts in my opinion make for the best experts. Those people have the self-awareness to acknowledge the shortcomings of your approaches. Doubt allows you to address those shortcomings and iterate to truly superior solutions. I never want to lose that. Indeed, the way to become a guest expert on a conference panel can be the same way to be erode your skills.

Nevertheless, I aim to get better at my craft. Right now, that is product management. And people often ask me how I have gotten better at my craft. Here’s how I think about it…

//This post is a part of Startup Edition http://bit.ly/1e2L9uJ - read how others have become experts at their crafts

Explore and be rigorous about your interest in the craft

It’s silly to become an expert in a field without thinking deeply about it at first. Indeed, many of us stumbled into our professions and industries. But imagine you haven’t committed decades to your field yet, and if you can, pause for a moment. Why do you want to be an expert in growth hacking? Or why do you want to be really good at solving access to essential medicine?

It’s going to be difficult to be an expert at anything you’re not either deeply passionate about or believe directly leads to some tremendously important next step in your life. Sure, it’s doable, but if you’re arguing that one should be an expert at something he or she doesn’t care about, we have bigger problems than semantics.

  • Meet with people already in the field

No better way to understand what product management, or basket-weaving, or accounting, is all about than meeting the practitioners themselves. Cold emails, tweets, friend-of-friend referrals, Meetup groups - this is how I and many others have done it. Don’t be ashamed to put yourself out there just because others seemingly got into the field without ever putting pride on the line.

Maybe you really love numbers and assumed accounting would be for you. But then you meet the accountant, and she is depressed and unexcited about her work. That could be revelatory. Or maybe the product manager misses the days when she was an engineer. Oh, you’re an engineer? You may realize your temporary dissatisfaction with the project isn’t cause to change fields. And the basket-weaver? Maybe the pure bliss he gets from his work convinces you to work for fulfillment, ignore a shrunken industry, and forsake stock options and a steady income.

Would you marry someone without ever meeting? Then why do that with your career?

  • Reflect on your motivations

Many of my friends from college went into management consulting. Why? Money, prestige, and exit options based on the training received during a miserable two year analyst program.

If these friends had articulated these motivations sooner, other paths may have seemed available. But they were locked into this career path handed down from previous classes who attended our college and returned to recruit the new flock of overworked analysts.

One night during my freshman year of college, my cousin asked me over second dinner in the middle of the night in a New York diner: ‘What are you planning to study?’ I responded, ‘Economics, so that I can get a good job.’ Saying so, somehow for the first time, made me realize the grand mistake I was making. It made me realize I didn’t want to be a person who traded the chance to pursue passion for a fatter paycheck. I switched to Sociology and Computer Science. Now, in hindsight, that seems obvious for a product manager, and I didn’t have to trade passion for compensation. But in 2007, I had no such hindsight.

I ask aspiring PMs why they want to do the role. For some, the reason is vanity. Imagine, for example, if the title was ‘Product Liaison’ or ‘Development Coordinator’. Would you still want the role or do you care about title? Many people then start to frown.

  • Imagine yourself in this field in 20 years

Maybe product management is the craft du jour. Maybe it won’t be around in 20 years. Simply thinking about the next 20 years may force this question. Will you still find the skills valuable? Will you be OK with the fact that no one will know what the job was about? Maybe I’ll be bored by it then. I don’t suggest planning out every year of your life - that’s often a wasteful exercise, especially if it incurs a lot of anxiety. But think longer term and question your investment in the craft.

For example, I really believe product management will serve me well, not only when I start my next company, but also when I go to development work abroad.

Practice your craft

  • Develop the mindset of obsessive practitioners

I advise aspiring PMs to evaluate products and services constantly. Why does Spotify promote playlists? Why does Facebook have ads on the right side and the feed? What would be the tradeoffs of Twitter removing the 140 character limit?

But also, why do toilets have separate lids, both of which you need to touch with your hands? Why do athletic stadiums structure entrances in the manner that they do? What are the tradeoffs of having people look at teleprompters during speeches?

  • Work on projects at your day job and execute well

You have to actually execute on the principles of the craft to get better. Some learnings only happen this way. Some learnings can only be proved this way. Solicit feedback and reflect on your performance as often as possible.

Learn from others

  • Quora / the Internet
  • Casual conversations with other PMs
  • PM Poker
  • Interview PMs

Teach others

  • At Yammer, we are trying to spread our product development methodology to other groups with Microsoft. This requires reflecting on how we build product and clarifying one’s own understanding and having it challenged by others
  • I launched my Udemy course. It forced me to refine my thinking and also opened up the class to an audience that raises a bunch of new questions.

Be perceived as an expert

This is my least favorite piece. It has nothing to do with the actual skill-building to be an expert. But what separates experts from people who know just as much or more than the experts? Self promotion and brand-building that leads others to believe one person is more knowledgeable than all the other equally qualified parties.

What do you do to practice your craft and become an expert? Is the concept of an expert evolving over time?

 //This post is a part of Startup Edition http://bit.ly/1e2L9uJ - read how others have become experts at their crafts.

Quartz UX Teardown: How to Design and Create Engaging Email Newsletter User Experiences

I have been reading Quartz daily emails for a couple of months now. That is amazing. I can’t remember the last email newsletter that kept me that engaged (I read the whole email daily) for that long (2 months+). Normally I would unsubscribe or set up a filter by now. But I haven’t unsubscribed from Quartz yet. And I rarely delete their emails without reading.


So what is Quartz doing right?

Easy and Useful UX + Consistent Delivery of that Experience = My Continued Engagement with Quartz

If you can delight people with an easy-to-use service that provides value, this will make them want to use your service again. If, upon return, that person enjoys a similarly valuable experience without experiencing much pain, it follows that that person will still want to use your service again. Follow that pattern enough times, and that person will habitually use your product until you screw it up.

Easy and Useful UX

Let’s pick apart the nuances of what works in the Quartz UX. Remember, this is an email newsletter. The Quartz UX is limited by email clients (Gmail, Outlook, etc.). But despite constraints, Quartz makes a number of smart user experience decisions.

1. Timing

I receive the Quartz email in the middle of the night (shown here at 3:02am) each day [1]. This is smart but risky timing. Consider the context.


Assume people read their email more or less first thing in the morning. On one hand, some people are in the mode of clearing out their inboxes to start the day fresh. The Quartz email, which is non-critical, would be the first to get deleted in this mode. That is the risk of sending the email overnight. It’s easy to give up on that half-hearted resolution “I’m going to be a more informed world citizen” when you’re half-asleep in the morning and stressed out by the rest of your inbox. That is the risk.

On the other hand, the morning can be a time for catching up on missed information, and Quartz helps you do just this. And in fact, no other time of day is better for this content because 1) there are opportunities to engage vs. in the busy middle of the day 2) the content becomes less valuable over time.

Opportunities to Engage

Mornings have a number of moments that one can read the news - in bed half-asleep, sitting at the dining table drinking coffee, during the morning commute, or any number of moments. The email as a medium is especially good for commuters because if its content is downloaded beforehand, people can read even when they lose Internet connectivity (e.g. in an underground subway). But conceivably, afternoons and evenings also have downtime (e.g. lunch breaks or evening commutes), too, right?

Information Decay

However, information suffers from decay theory, which suggests that some information (like the news) is less valuable with the more time that passes. So the morning time is uniquely a good time for sending a newsletter with world news given optimal relevance. Moreover, even if you did assume that people wait until the middle of the day to check their email, then it’s likely the Quartz email has gotten buried. People will only get engaged with Quartz if a person 1) somehow still sees the email 2) is so bored / available in the middle of a work day. Those are bad odds.

2. Email Subject Line Anchoring

At this time of day (first thing in the morning), the email would also probably be showing adjacent to a bunch of spammy offers and other unwanted things dropped into your inbox overnight. While many of us do have coworkers sending emails through the night, it’s more common for marketing emails to be the source of morning clutter. For me, a number of other automated emails happen to show up overnight. So relative to the other emails, this Quartz email stands out as high quality and worth opening. Note that this anchoring is something Quartz may not be able to control, but that doesn’t mean they can’t predict and exploit it.


Which email do you think I’ll read out of all of these?

Email subject line anchoring isn’t all that different from price anchoring, which helps people sell expensive items that simply seem relatively inexpensive when placed next to an even more expensive item (i.e. an $8 beer seems cheap relative to the $14 mixed drinks at the bar). On the other hand, if the Quartz email showed up around 11am or 2pm, I’m likely getting emails from my boss, close friends, and other highly relevant and/or important people. In that anchoring scenario, the Quartz email would seem trivial and either not get read or get deleted.

3. Compelling Subject Line (Before it Gets Cut Off)image

Quartz squeezes in major news about Iran, the UN, and what I guess might be China. I’m compelled to check it out.

Every day the subject line is different enough to entice me, but similar enough for me to identify it with a quick glance. Also, it manages to do all of this within the display character limit.


The full subject line

People who build products sometimes get caught up in our own feature sets, rather than the benefits delivered to end users. This leads to subject lines like “<My Company> Releases New Syncing Features!”. Or we simply are not thoughtful during this product development moment and construct subject lines such as “<My Company> Report for 01/01/2015 18:30 GMT” when the easy, lazy thing to do is just rely on simple and systematic subject lines.

If you already have a strong relationship with users or have a user base who really wants zero personality from your product (sadly, some enterprise buyers prefer this), then fine, this style of a subject line may still manage to command decent open and click-through rates. For me, this is the case for Google Calendar daily agenda emails.


However, Quartz is a relatively new service (lacks the existing engagement Google Calendar has). Knowing today’s news frankly is less critical than knowing your daily agenda. Missing a meeting with your boss is more immediately painful than missing news about the latest war overseas. All of this despite how important that war is to world peace, and your meeting is just about you. So, punchy and meaningful subject lines are essential to keeping open rates, and subsequently click-through and engagement rates, high.

4. Personality

Even with a generic grouping into ‘Quartz Readers’, I am glad that at least Quartz took the time to say “Good morning.” Even though I hear and say “Good morning” countless times to peers and coworkers throughout my day, it’s nice to read it first thing in the morning from what could otherwise easily be a robotic feeling newsletter. Feeling like someone is on the other side of the message makes me almost feel like someone real is curating my news for me.


Good morning to you, too, Quartz!

Quartz could just end the email. But Quartz takes time to say goodbye to me and wish me bon voyage for the day.


Quartz closing strong with a nice, personal touch at the end of the email

In closing the email, Quartz wishes me a productive day. You know what? “Productive” is a key way in which I measure my day. So now I feel like Quartz gets me.

While not everyone prioritizes “Productivity”, mostly everyone will react positively to this wish (accomplishments = good) and it is far more original than “Have a great day!” And originality begets a memorable experience.

And this closing is different everyday. Notice the tidbit about “Chinese Winnebagos”. It relates to this story here earlier in the newsletter.


When I really dive into my subconscious, I think I get a little chuckle out of this little closing every day. So I feel motivated to make it to the end of the newsletter.

5. Laundry Lists are Lazy; Hold My Hand and Show Me Why I Should Care

Quartz has a problem. There are dozens of valuable stories to share every day. One single list of article after article is hard to parse and hard to scan when necessary.

Remember what Yahoo looked way back when?image

Instead, Quartz breaks out articles with logical and consistent categories. The categories have personality (vs. “Category 1”, “Category 2”, “Category 3”) without losing clear meaning.

Notice how easy it is to take how Quartz labels the article groups and make sense of them.


“Chunking” is a classic psychological concept that aids memory. But is also extends to processing an email newsletter’s contents. Indeed, “Input chunks reflect the limitation of working memory during the encoding of new information.”

Focus My Attention on the Right Things

As we mentioned, Quartz is limited by the presentation of information in an email client. The newsletter avoids images with stories, perhaps because it would often not show up with those that have images turned off, the mobile rendering would be challenging, and scanning would be harder.

So with just text, and basically bolding and hyperlinking, at its disposal, how does Quartz manage to focus readers on the most important content?

  • Consistent, bold lead-ins for each story. This lets me scan easily and is an obvious tactic. As obvious as it is, a lot of blog posts have no structural consistency to what is bolded and what is not - it’s a subjective reflection of what the creator deems interesting.image

  • Strategic hyperlinking. Notice in the first story how one scan and catch “discuss the resolution”, “will meet his Iranian counterpart”, and “hailed a ‘new era’ on nuclear talks.” While perhaps a little superficial, scanning gets us pretty far and we’re guided by what Quartz chose to bold and hyperlink.

6. Facilitate Further Action Without Forcing It / Have My Back

It may be common practice by now, but the simple practice of accurately linking to parts of statements that need more evidence or support makes me trust Quartz. If I want to read more about the specific resolution John Kerry and the Iranian counterpart were going to discuss, I can dig into it. But Quartz by no means forces me to consume that content if I’m not interested. As a result, I don’t feel like Quartz is trying to persuade me of anything, but rather present facts and let me pursue further information if I’d like to do so.

Do you know email newsletters that are well-designed? How do they achieve a delightful UX?

[1] I did not find a setting that lets one determine when they receive the email. While some users may complain about a lack of control, not having this setting reduces engineering and UX complexity for Quartz. Notably, the timing for weekend emails is 4:02am, so Quartz must be trying to be, at least for subscribers to its Americas Edition, hitting people around 6am ET during the week and 7am ET during the weekend.


Yelp UX Teardown: Driving More Reviews By Slaying Friction and Leveraging Familiarity


I rarely write Yelp reviews. But this morning, I did. And I didn’t have an extremely good or bad experience. Rather, Yelp made an extremely smart product move and generally solid implementation. Here’s what happened.


1. “Reduced Friction” - Yelp finally made it easy to leave a review by placing the review form smack on the front page with the copy “Your Next Review Awaits”.

But reducing “discovery friction” wouldn’t be enough to get me to leave a review if the interaction was clunky. The “interaction friction” was also low. One click and I can give it 4 or 5 stars, or whatever I choose. And there’s just one text field. That’s not intimidating (note that the review UI begins as a small text field and expands to a larger text area to avoid scaring you with a big commitment). It would be “reasonable” to have multiple fields (ask separately about service, food, ambiance, etc.). For example, the full review page is more intimidating even though it fundamentally just wants to collect the same basic review info. But yet Yelp used a very focused version of its review submission interface to increase the rate at which people begin to fill out the form and decrease mid-review abandonment.

imageHomepage Review Element



The normal review page

2. “Leveraged a Sense of Familiarity / Context” - I had dinner with my girlfriend last week at Contigo. Like many of our meals out, we mentioned it to friends we saw at a party after dinner, and it’s come up once or twice since then between the two us. We formed a positive association with the restaurant through natural, non-commercialized and largely non-digital social interactions. So when I saw the name “Contigo” again when I fired up Yelp, I got a brief warm/fuzzy of familiarity. And then I imagined myself there again, and the people we interacted with during our dinner (hostess, waitress, the nice man who poured the water, and our nearby diners). All of a sudden, I honestly felt an obligation to credit them.


The photo from the venue adjacent to the review box pulls even more at my heartstrings, even as just a thumbnail sized photo


Everything from the website, to the postcard attached to our bill (to send to someone out of town, perhaps), to the name ‘Contigo’ (Spanish for “with you”) all contributed to this positive association

3. “High Signal to Noise Ratio” - Yelp leverages OpenTable reservations as a signal that I actually went to the restaurant (whereas my visiting a review page alone is a much weaker signal). So it’s very likely I actually *did* eat at the restaurant. Also, Yelp shows my most recently reserved reservation (Contigo) first as opposed to the place I went previously (Campanula) - that one shows up after the first, most recent restaurant. Smart - I’m more likely to remember and feel compelled to write something about the place I went last week vs. 2 months ago. Separately, if Yelp had a deep integration with OpenTable, which can tell whether or not I *actually* went to the restaurant and used my reservation, Yelp could further improve the signal to noise ratio, i.e. don’t show me the option to review restaurants I made a reservation at but didn’t go to. One day when Yelp owns the reservation system, too, this will be easier for them. 

Additionally, Yelp reminds me of this reservation vs. just hoping I recognize the restaurant.


But here are 2 UX mistakes Yelp made with this flow…

1. Took me out of context after the first review After I leave my first review, I was really hoping they would keep me on the same page, in-context, letting me mow down my unreviewed places.

Instead I got dropped here…


You *can* find where to go to continue the reviews, but it’s not as simple and snappy as just keeping me on the homepage, show a success message in that box (maybe with an option to click to the review or restaurant page in a new tab), and move me to the next restaurant.

Generally speaking move me from A to B…




On the other hand, Linkedin keeps you on the same page when you’re on the ‘People You May Know’ and I’ve heard it’s wildly successful at the ‘Connecting’ process, which could otherwise be scary and awkward.


2. Visually and behaviorally disconnected social sharing after the posting of a review 


People take time and care to post Yelp reviews. Why is there such a separation here? It breaks context. It’s ironic if you look at the name of the page. image

Normally a site will really push people to share to Facebook or Twitter right after. For example, this is what Eventbrite does after you register for an event.


Now I’m going to finally go leave that review I originally intended to post before I got distracted by the Yelp UX…

[Discuss and upvote on Hacker News]

Product Manager Interview Questions

 Here’s a list of questions asked in recent PM interviews (Spring, Summer  2013). Respond to any in the comments and we can chat about them  here!
- Pick a physical product and improve it.
- Explain recursion to your grandmother 
- How do you work with engineers?
- What’s a PM challenge that you overcame?
- How do you convince management?
- What’s a product that your’e proud of?
- Describe what happens from the time you type a URL in a browser and you see content on a page?
- How do you optimize page load performance? 
- What nascent technology are you excited about?
- How would you improve a garage door opener?
- What are the use cases for a traffic cone?
- What are the unique properties of a traffic cone?
- What product do you dislike & why?
- How would you design the YouTube related vids algorithm?
- What metrics would you use to evaluate the success of the YouTube related vids algorithm?
- How would you design the Kindle server?
- What’s the maximum bandwidth you’d need to support?
- What’s your favorite video conference software & why?
- How would you improve it?
 - What’s the maximum resolution you could support on a 200KB connection?
Any questions to add? I’ll continue adding to this list over time and as people share more.

Product Manager Jobs and How to Get Hired as a Product Manager

It seems like “Product Manager” is a really hot job these days. Many of my friends - old and new alike - are now interested in the role.

And indeed, it’s a great position in a tech company. Learn how to prioritize features, build beautiful user experiences, interpret A/B test results, work with brilliant designers and engineers, and much more.

So I decided to build an online course called “You’re Hired: How to Get a Job in Product Management”.

Here’s the intro video and a promo code to get 50% off of the course with the code “shahblogfriend”.


Any feedback on the course? I’m excited to already have about 30 students taking the class in barely a week on Udemy. It seems like a great platform for spreading the course widely.

Identify + Hustle: How to Land Your Dream Startup Job

"The Startup World" can be a confusing jungle of bits, bytes, and billion dollar acquisitions to outsiders. Here’s how to break into it.

This post is part of Startup Edition. Want more advice? Startup Edition has posts from other bright minds in the startup world on this same question. http://bit.ly/18O0pqs

Identify Companies

Unlike people immersed in the startup world, you may not know which companies are taking off, hiring, or a good fit for you right off the bat. Here’s how to do fix that.


Where do I find these companies? I recommend browsing AngelList and CrunchBase and creating a Google Doc of interesting companies. While flawed, there are articles online listing “Hot Startups” that can be an additional input. There are hot startup lists on Quora specific to a wide range of cities, and plenty of articles in the tech media like this one from TNW and Wired. Additionally, each month Hacker News (run by YCombinator) has a ‘Who is hiring?’ thread like this one from August 2013 and a persistent jobs link for their startups. Additionally, look at the portfolio companies of top venture capital firms and accelerators/incubators for more sources (Sequoia, Kleiner Perkins, Khosla Ventures, First Round Capital, YCombinator, 500 Startups, and many more). Some VCs also build talent pools for their startups, such as this one from Andreesen Horowitz.

How do I know if these companies are right for me? I recommend looking at size, stage, sector / industry, culture, the founders, your role, and some other factors. Do you want to join a 5 person team or a 500 person company? Do you want to go to an early stage place (high risk, high reward. opportunity to shape things but perhaps less structured learning), or a company surely headed for IPO (less potential upside but more secure future and a good place to learn)? Are you interested in 3D printing, enterprise social networks, photo sharing, APIs for health data, etc.? Try to figure out what you are passionate about, or look at companies and think about whether what they are doing is interesting for you. Is the culture meritocratic and fun, or is it bureaucratic and stifling? It won’t be that black and white but through reading about the company, meeting people who work there, visiting the office, etc. you should be able to parse this out. What will be your role anyway? If you will be working on product, dig into what the relationship is like with engineering, and how autonomous product is, and how skilled the designers you’ll be working with, etc. If the company has a baked product that doesn’t need much work, maybe it won’t be that interesting.


Figure out what those companies need or expect from you and do it. Go above and beyond.


Some people have built websites specifically declaring their love for the company and what they could deliver, like Alice Lee for Instagram (who was instead hired by Path). Other people like Tristan Walker cold email founders (at Foursquare) 10 times, work for free for 30 days and show real value, and then get hired full time and dominate in the role. Tristan’s advice to people looking to get into startups is simple and to the point:

“be so enamored with the product that you would work for the company even if they didnt hire you….more importantly find where the needs are within the organization and be willing to do whatever it takes to help them fill the need (work for free even!)…and MOST importantly make sure that youre filling a need that the organization doesnt have the resources to fill on its own. If a company is not willing to let a hungry, passionate, smart, unpaid advocate of the product help the organization to fill that need (when it doesnt have the resources to do it itself) then you probably shouldnt be working at the company anyway. They’re just being arrogant” - tristan walker http://justtristan.com/post/7696394458/two-years-ago-today

Build side projects to show what you’re capable of. Go to hackathons. Be active on Github and in the open source community. Network through Meetups and General Assembly. Reach out to people who work at the company via Twitter and Quora; take them for beer or coffee. Blog and do product teardowns to show your product sense. Before I joined Yammer, I blogged a lot to create a place where people could easily see how I think and in fact did product teardowns like this one on Airbnb. (still do!). Hustle.

There will be many roadblocks. Some calls will not be answered. Some people won’t think you can make the jump from corporate employer to move-fast-and-break-things startup. You may have to debate whether to take a pay cut. Whether to take a marketing role when you really want to be doing product. These are the things that make this simple process not so simple, but if you are persistent, thoughtful, and resourceful…just like everyone else before you, you will figure it out.

This post is part of Startup Edition. Want more advice? Startup Edition has posts from other bright minds in the startup world on this same question. http://bit.ly/18O0pqs

Shutting Down Instead of Pivoting

“Angry Birds was Rovio’s 52nd game. ….Startups are hard, but they can also go from difficult to great incredibly quickly. You just need to survive long enough and keep going so you can create your 52nd game.” - Chris Dixon, “The Myth of the Overnight Success”

Rovio didn’t pivot. Rovio kept making games even in the face of bankruptcy in early 2009.

[This post is part of Startup Edition - see what other brilliant people in the startup world have to say about pivoting.]

But how do you know when it actually is time to pivot away from an idea? How do you know with confidence that you’re not onto something and your 52nd title is not around the corner? Indeed, the very same believing that keeps you going is very similar to the same believing that led you to take the initial leap in the first place. How do you ignore sunk costs?

It is not easy. But clearly we are all not Rovio. Capital, employee morale, and personal strength are all finite. We cannot all go on indefinitely.

In my experience, it boils down to a brief but complex question: have you disproved your core hypothesis?

Read More

Aug 1

Startup Resources

I’m going to compile a bunch of the best resources for very discrete startup purposes here. Let me know if you have ideas (me@jasonshah.org). Thanks to McKenna Moreau for kicking this list into high gear.


Product-Market Fit



  • How to Sell with Noah Kagan (video)
  • How to Set up a Sales Teamimage

(and New Sales Models with David Sacks)

Partnerships / Business Development

Resources? me@jasonshah.org

Product Management

Resources? me@jasonshah.org


Resources? me@jasonshah.org


Resources? me@jasonshah.org


Resources? me@jasonshah.org







It’s a Marathon

I was a young entrepreneur (17) when I launched my first company, INeedAPencil.com, from my parents’ home in Florida. Honestly, I am just 23 now, so…

//Other entrepreneurs answered the same question (What advice would you give young entrepreneurs?”) They are smart people, with less frightening headshots. Read here

At the time, I thought it was a good idea to send bloggers a headshot that looked like this:


“Anyone want to buy a used 1992 Mazda Miata?” In this photo, I appear to be a used car salesman, who happens to be missing my left ear. Hadn’t mastered Photoshop yet (or still). Google Image Search is unforgiving into your 20s and beyond.

Tip #1: Get a second opinion on the basics, and don’t be defensive about constructive criticism - it’s your best friend.

For example, in addition to my headshot wisdom, I negotiated the sale of the company on my own over the phone. Many rookie mistakes were made, and I definitely didn’t structure the deal well. So none of this “advice” is black and white, and you should realize now that everyone’s advice to you is colored by their own experiences and sometimes not applicable to you.

The Flipside: I named the company “INeedAPencil.com”. No adult would have advised this. It still baffles my accountant and anyone to whom I tell stories about the company. But it stood out, helped get press attention, made it feel authentic, and helped on the SEO front. Better than FreeSATPrep123.com, right?


I also worked hard as hell. Honestly, that was mainly because I didn’t have many friends when my family moved to Florida in the middle of my high school years. But I also had the energy at the time. I would wake up at 4am to talk to the developers in India, reply to emails during “passing time” in high school, and so on. I drove around Florida sticking flyers in people’s windshields. I wrote hundreds of SAT questions, so that my website could have original content. I had my fun, but I definitely missed out on going to the movies every Friday night because I thought I was working on something important. But that’s what I wanted.

Tip #2: Sleep is important, sure, but if you have the energy to work hard, go for it. You may not have the same energy or chutzpah when you get older.


The Flipside: Did I miss out on aspects of high school that were valuable? Maybe. Could I have figured out a better business if I wasn’t so impatient? Maybe.  And who knows what personal development I missed, but I felt like I was having fun when I hung out with friends and could work hard other days / when I got home. Figure out what’s right for you.

INeedAPencil.com is an SAT prep website. It monetized through lead generation for colleges. Initially it was a paid service, but honestly, very few people signed up. So I arrived at this business model eventually. I’ll leave out the social-good aspect for simplicity for now.

Here I was, working on an important social issue (equal access to higher education), jazzed up from the terrible educational access disparities I saw when visiting my sister’s classroom (she was a Teach for America corps member) and her students in West Philly in 2005.

But was I passionate about education? No, not really. Did I love test prep? No, not really. Yet here I was, gunning away, eventually helping around 100,000 high school students from low-income families improve SAT scores. But everyone kept saying that we young people should be doing what we were passionate about, and I didn’t know what that was for me.

Tip #3: You can be passionate about running your business and making an impact, and what you’re working on…even if you’re not passionate about “what you’re working on.”

I was never that deeply passionate about education, but I cared a hell of a lot about building a business that worked. Now I realize that’s OK.

Did the Airbnb guys care about scarce hospitality options or overpriced hotels? Doubt it. Did Mark Zuckerberg really want to “make the world more open and connected” when he launched TheFacebook.com? Doubt it. Is anyone building enterprise software truly, deeply passionate about what they are working on? Um, no.

I feel like tech entrepreneurs chasing passion is sometimes like hopeless romantics chasing true love as depicted in Hollywood movies. They read the Inc. Magazine profiles of successful entrepreneurs, wishing on a star to discover their own passion for airbeds or social networks.

What I enjoyed most was building the website, talking to students, measuring success, and so on. None of this was truly the problem I was solving. Honestly I could have done some of this for accounting software and be just as excited (OK, maybe a little less excited). But I was passionate about running and growing the business. That can be what you’re passionate about.

The Flipside: I could be wrong about this. Maybe if I were more deeply passionate about education, INeedAPencil.com could have reached 1 million students and IPO’ed.

You will be a “young entrepreneur” for a long time. Buckle down, but enjoy the ride.

//Other entrepreneurs answered the same question (What advice would you give young entrepreneurs?”) They are smart people, even though they don’t have headshots like I have =) Read here

Some productivity tactics

1. Email oneself with 3 top priorities for the day the night before. Hard to build this habit, but worthwhile. I don’t like cluttering my email, but 1) there are far less important emails in my inbox 2) that “clutter” leads to a constant reminder to get X done. Use the subject line for the tasks themselves, so it shows up at the Inbox List level (more reminders) and the subject line from day to day doesn’t get boring / easy to ignore.

2. When working on a key task, pull out the tab in the web browser, so it’s the only page one can easily see. It reduces the triggers to check other tabs and limits distractions generally.

3. Listen to acoustic music at a high enough volume that one can’t hear anything going on in the office around him or her. Again, limiting triggers.

These are some things I have been trying lately (just the past couple days). Limiting triggers. Additionally no email before noon (when possible. weak resolve, I know) has been effective. If you have to check it, just check it but don’t get sucked into replying before you need to and making a shooting range out of your Inbox, as you’re sucked into trying to nail every last target. Some of these were inspired by James Clear’s recent post on the Buffer blog about 8 ways to improve your morning routine.