PM Tips: Replace excessive 1:1s with office hours

As the product leader for a large team at Thumbtack (30+ across 3 groups), it was challenging to stay in sync with all my team members. I tried scheduling recurring 1:1s with everyone, but that led to meeting overload for people who weren’t direct reports (ex. engineers who already had 1:1s with their engineering manager). I found reducing 1:1s and setting aside time each week for office hours to be a more efficient and flexible solution.

To get started, I blocked off time each week exclusively for team members. I used a two-hour block of time twice per week. I put my office hour blocks after lunch on Tuesdays and Thursdays since both early birds and night owls are in the office, it incurs lower context-switching costs, and it makes sure I’m available both early and late in the week. I kept them at the same time every week so my team didn’t have to try to guess when I’ll be available. Thumbtack uses Google Calendar as a source of truth for scheduling, so I put the office hour blocks on my calendar, and team members were free to schedule meetings over the blocks on a first-come-first-serve basis. Most meetings don’t take the full 2 hours (15-30 minute check-ins are most common), but it’s important to have longer periods available for deep dives.

I made it clear to the rest of the company that office hours are exclusively for members of my team, and I was unavailable for other meetings at that time. If you want to give office hours a try, be firm about enforcing this rule, or non-team members will treat them as convenient times to schedule you up for meetings, interviews, etc. People were constantly vying for my time, and office hours were my commitment to being consistently available to my team.

In the beginning, I had to actively encourage people to use office hours because people weren’t sure when it was appropriate to use them (hint: it’s always appropriate). When people came to me with questions and I didn’t have time to give a proper response I’d tell them to sign up for office hours. I would also schedule time with team members who I hadn’t caught up with recently. The beauty of office hours is that they’re more flexible than formal 1:1s. Your team should be comfortable using them for anything — discussing concerns about company strategy, brainstorming ideas, or just generally catching up. Over time, my teammates became increasingly proactive about leveraging of office hours and I enjoyed being able to provide them with my undivided attention.

Office hours are an effective tool for busy product managers, but they are not a complete replacement for 1:1s. I still supplemented office hours with recurring 1:1s with direct reports (weekly or bi-weekly) and formal 1:1s with all other team members at least once per quarter. By replacing nonessential 1:1s with office hours you get the benefits of staying tuned into what’s going on with team members without the productivity cost of excessive meetings.

The best book I read in 2017

I consider myself more rational than average. I’m an even-tempered CS major, and a decade working in product and growth trained me to scrutinize intuition with objective data. When my wife and I argue, I try to be rational to the extent that she pushes me to think less and emote more.  Before reading Thinking Fast and Slow by Daniel Kahneman, I knew that I still make irrational judgments, but I assumed that when making important decisions I could deliberately put myself into in a rational state of mind. Reading the book changed my thinking.

The book walks through Kahneman’s research into how humans rely on heuristics to function more efficiently and how they often lead to irrational decisions. More importantly, it shows that everyone exhibits these failures of reason regardless of education, expertise, or training. It even gives examples of how Kahneman himself, the leading expert on behavioral economics, consistently falls prey to irrational thinking. The book is full of interesting insights, but three in particular captured my attention.

Loss Aversion

Loss aversion is a well-known concept that I was already familiar with — you feel more dissatisfaction from losing something (ex. money) than satisfaction from gaining something of equal magnitude[1]. However, I never considered the powerful second-order effects of loss aversion that Kahneman explores.

Loss aversion creates a tendency to maintain the status-quo. In order for someone to choose to break away from the norm, the expected value of change must be irrationally positive. Similarly, it leads to the “endowment effect” where we place excessively high value on an item we possess. Suddenly a whole swath of common behaviors — hoarding, remaining in bad jobs and relationships, and the curiously strong pain of unmet expectations start to make sense.

For me, the most surprising consequence of loss aversion is that when presented with a set of bad choices, people become more risk seeking. That has disturbing implications from a societal perspective. Consider a person who is struggling financially and faced with an array of undesirable options (filing for bankruptcy, taking an ultra-high-interest loan, etc). They are likely to choose the option with lowest expected value if it has a minute chance of yielding the best outcome. In other words, human nature may cause people in bad situations to end up in worse situations more often than not. After finishing the book, I constantly find myself considering the role of loss aversion in the world around me — a startup’s sudden pivot when cash is running low, annoyance when a loved one fails to intuit your feelings, and more.

What You See Is All There Is

We make decisions based on the information immediately available to us and as far as our subconscious decision-making is concerned, all other data is outside the scope of reality. Again, confirmation bias, recency bias, etc are all familiar topics, but reading about how core WYSIATI is to our thinking made me consider the ramifications more deeply.

If WYSIATI is true, rational dialogue might always be doomed to fail. Even people who sincerely agree to have a logical discussion will be subject to a stream of unconscious judgments driven by whatever information is most easily accessible. In this scenario, facts become irrelevant, and maximizing the mental accessibility of your desired message  (ex. by continuously repeating simple memorable phrases) is the optimal strategy for winning followers. The fact that I’m not immune to these strategies makes me extremely uncomfortable, and you can extrapolate how they may have played a role in recent US politics.

Regression to the Mean

I like this theory because even though I understand it, I feel my mind rejecting it in practice. According to Kahneman, humans are particularly terrible at recognizing randomness and regressions. As a result, we make up completely false but highly convincing stories to explain data that is better explained by random events. Consider the following statement from the book:

Highly intelligent women tend to marry men who are less intelligent than they are.

When I read it I immediately started coming up with explanations for why this is true, but I did not consider why it’s trivially obvious mathematically. If the distribution of intelligence for men and women is roughly equivalent and the correlation of intelligence between spouses has any degree of randomness (ie the intelligence of your spouse cannot be perfectly determined based on your intelligence) then of course a woman who skews to the high end of the curve is more likely to marry a man who is lower on the curve.

This concept sticks with me because even after accepting the statistical explanation, I still feel compelled to attribute it to other, much less likely reasons. Anyone who works in product or growth should keep this in mind when trying to interpret stats. It’s far too easy to get carried away with your own story when you’re really just looking at random data.

Mitigating our irrational selves

I’ve become more concerned about living in a world where we all constantly make irrational decisions. It’s helpful when I remind myself that relying on heuristics isn’t all bad. Most of the time they help us efficiently make rational (or sufficiently rational) choices. If I had to stop and consider every decision I make I’d never accomplish anything.

I’m also starting to craft environments and principles that will help me guard against my blind spots. I know I will demonstrate unconscious bias when making decisions. However, by establishing a rational decision-making algorithm beforehand and adhere even if it deviates from my in-the-moment intuition, I can reduce irrational errors. I found Principles by Ray Dalio useful for helping think through my personal set of principles. Unfortunately, just outlining principles isn’t enough. The next step is to have some set of objective 3rd parties (friends? coworkers? AI assistants like Siri and Alexa?) actively holding me accountable. Figuring that out is still very much a work in progress.

A new favorite

I let Thinking Fast and Slow linger on my to-read list for far too long. I assumed I knew the content based on all the books/posts/podcasts that reference it, and I had recently refreshed my understanding of cognitive biases by reading The Art of Thinking Clearly by Rolf Dobelli. I was finally motivated to pick it up after reading The Undoing Project by Micheal Lewis, which details the friendship between Daniel Kahneman and Amos Tversky that generated the research behind Thinking Fast and Slow. As it turns out, you really need to read the book. Pieces that reference it only give a small peek into the robust mental model that Kahneman presents.  In an ideal world, I would suggest first reading the Undoing Project, then reading Thinking Fast and Slow, then skimming The Art of Thinking Clearly and keeping it handy for quick reference. Whether or not you read the others, don’t neglect Thinking Fast and Slow. It’s a fundamental book that everyone should read. It changed how I view myself and the world, it has practical applications, and it raises tricky moral questions (is it wrong to leverage these theories to manipulate others?). It took me awhile to get to it, but it ended up being the best book I read in 2017[2].


[1] This is an oversimplification that doesn’t account for factors like framing and reference points.

[2] Sapiens by Yuval Noal Horari comes in a very close second.

SEO 101: The three pillars of great search strategy

I had the privilege of learning the intricacies of SEO from Luc Levesque, one of the top search experts in the world, and Sander Daniels, co-founder at Thumbtack. During that time, I discovered that the bleeding edge SEO needed to capture and maintain top search ranks requires an enormous amount of effort and creativity, but building the foundation for strong SEO is fairly straightforward. There are 3 foundational pillars for any great organic search strategy. I consider these table stakes for SEO — they won’t get you to the top of the search results, but without them additional SEO efforts are futile.

I. Technical SEO

Technical SEO is necessary to ensure search engines properly index and display your site. It includes creating a logical site hierarchy, good HTML hygiene, using appropriate search engine directives, optimizing page performance, and more. There are dozens of technical SEO guides and checklists available  online, but for beginners, I recommend working your way through Google’s SEO Starter Guide. Take the time to understand every point and read the linked documentation. At this early stage, you should also stick to getting comfortable with Google Webmaster Tools and Search Console rather than signing up for expensive 3rd party tools.

II.  Content

Every site that wants to capture organic search needs an SEO-optimized content strategy. Start by identifying the set of keywords you want to target and establishing the appropriate page templates. Here’s how to do it:

1. Use a keyword planning tool to identify high search volume keywords that are relevant to your site. Early on, when you don’t have much domain or page authority, you’ll want to target less competitive words even though they don’t have as much search volume. A good trick is to go after specific queries like “five-minute vegetarian pizza recipes” instead of “pizza recipes.” This also makes it easier to create targeted content since the user’s search intent is less ambiguous.

2. Once you have a set of target keywords, run a full content analysis on the top 10-20 sites that rank for those queries. Make note of everything — search result titles, page design, page content, calls to action, etc. Google considers these the best pages for addressing these queries, and your goal is to identify all of the common elements among them[1]. This will give you the basic requirements for any competing pages that you create.

3. Define your special sauce. This should be something unique to your product or service that directly addresses the query and isn’t offered by competing pages. To continue with the pizza recipe example, you could feature a high-quality video showing a chef demonstrating the recipe or a call to action letting users order all of the necessary ingredients.

Use these steps to create baseline page template for each keyword. By following your template your landing pages content should already be as good or better than the competition.

III. Backlinks

Google’s search algorithm started with backlinks as the sole measure for determining Page Rank. Nowadays there are hundreds of ranking factors, but, in my experience, links are still necessary for getting enough domain and page authority to have a shot at top search ranks[2]. Unfortunately, links are a rampant source of abuse and blackhat SEO, so Google sets a high bar for good links and actively ignores (or even penalizes) bad links. Generating high-quality backlinks from scratch requires significant active outreach. The following are two strategies that I’ve seen work. Choose the one that best fits your product or service:

Solicit advice or feedback

Let’s say you want to get links to your tutorial for learning how to write object-oriented JavaScript. First, write a polished, informative tutorial (contract with a professional writer if you don’t have one in-house). Next, send your tutorial to every well-regarded JavaScript expert you can find and ask them for feedback. Prioritize people with a strong web presence since they’re more likely to be considered domain authorities by search engines. Keep reaching out until you get multiple responses, then rewrite your article with their feedback incorporated. When your revisions are complete, post the tutorial online and send everyone a link to the finished article thanking them for their input. With a bit of luck, some of the experts will link to your tutorial from their website, blog, or social media accounts. By prioritizing experts with a large web presence you increase your chances of having their followers link to your content as well. With continued effort, you’ll end up with a small set of high-quality, high-authority backlinks.

Surface and share unique insights

Dig into your internal content and data and look for interesting information that isn’t available elsewhere. When you find something unique, craft a comprehensive article around it. Make the article as easily digestible as possible by including stats, rich infographics, and key takeaways. The Priceonomics blog is a classic example of this kind of  content. When your article is ready, send a custom message that includes a summary and a link to the full article to everyone with an online presence that might find it relevant. For example, the Priceonomics team might send their  “Where is Pizza the Most Expensive in America?”  article to every Pizza shop in America, every major food delivery company, local news stations, etc. This is a numbers game — the bigger your list of targets the better chance you have of getting links. Keep in mind that you must earnestly offer up the data to all of your targets with no expectation of receiving a backlink in return — explicitly asking for backlinks is frowned upon by Google.

Looking ahead

Nailing technical SEO, creating engaging keyword-targeted content, and securing high-quality links is just the first step. With a strong foundation in place you’re ready to start competing for the top of the search results page. Be prepared for a long road to success. Constantly changing ranking factors and a zero-sum landscape make SEO a continuous process, and SEO work often takes a long time to bear fruit (experiments can take months to yield significant results). That said, organic search remains one of the most potent sources of online traffic, and as your site gains authority it becomes easier to capture search rankings. Stay tuned for future posts on tactics and strategies for boosting search traffic and building an SEO-focused growth team. If you’re eager to get started on further SEO work immediately, I recommend checking out the Whiteboard Friday posts on


[1] I exclusively refer to Google search in this post. Google is still the dominant online search engine, and most other search engine rankings mirror them. Focusing your efforts optimizing for Google yields the best ROI.

[2] For more on the importance of links see The Two-Part SEO Ranking Model.

Thanks to Sander Daniels and Luc Levesque for reading drafts of this post.

PM Tips: Master your inbox

As a product manager you receive a constant stream of emails. As a result, I recommend that all new PMs establish a system for managing their inbox in order to avoid email overload. A good email management system has two key requirements: process incoming emails quickly and ensure you don’t miss critical deadlines and info. There are numerous “inbox-zero” tools and techniques, and they all have their unique pros and cons. Try a few options and stick with the one that best suits your work style. After some experimentation, I now use the 5 Inbox Method combined with  Boomerang for Gmail[1].

The 5-inbox method is simpler than it sounds. You create 4 email folders in addition to your main inbox: Today, This Week, This Month (or This Quarter), and FYI. Whenever you receive an email, file it into one of these folders and process accordingly. The time-specific folders force you to do some quick and dirty prioritization, and FYI provides an easy way to track informative emails that don’t require a response. At the end of every day, make sure you’ve addressed everything in the Today folder, and do the same at the end of every week and month for their respective folders.

The 5 Inbox Method works well for processing incoming email and identifying immediate priorities, but it makes it easy to lose track of medium and long-term deadlines (things that fall into This Week or This Month). That’s where Boomerang offers an ideal complementary solution. In addition to filing an e-mail under This Week or This Month, if there’s a specific deadline associated with the email I use Boomerang to schedule it to return to my inbox at the appropriate time. Even if I don’t get a chance to process items in This Week or This Month I don’t miss important deadlines. As an added bonus, Boomerang is great for follow-ups. You can schedule any email (received or sent) to return to your inbox if you don’t receive a reply by a specific time[2].

I found this combination so effective I started using it for my personal email as well. For further tips on implementing the 5-inbox method see The Only Five Email Folders Your Inbox Will Ever Need by Fast Company.


[1] Disclosure: If you sign-up for a paid boomerang subscription with this link I get 1 month of free service. I recommend starting with the free tier that allows up to 10 boomerangs per month to see how you like it.

[2] Boomerang is great for Gmail and Outlook users, alternatively, Google Inbox has many similar features already built into the service.

Words of wisdom from Naval Ravikant

Back in 2012, I was kicking around ideas for a new startup, and a mutual friend introduced me to Naval Ravikant because he was “a pro at finding holes in ideas.” We spent an afternoon chatting about startups, being a founder, and the work he was doing at AngelList. I enjoyed our conversation and even seriously considered abandoning starting my own company and applying to work with at AngelList[1]. One particular piece of advice he shared stuck with me, and I continue to share it with aspiring entrepreneurs to this day:

Don’t start a company unless you’re willing to work on it for 10 years.

A succinct way to sum up the level of commitment you should have before starting a company. Startups aren’t a fast-track to riches. Most fail, and even those that succeed take 7+ years on average to exit[2]. If spending a significant portion of your career on your current idea doesn’t excite you, it might not be the one for you.

[1] I ended up co-founding HeartThis, but we did use AngelList to help with our fundraising.

[2] See CrunchBase Reveals: The Average Successful Startup Raises $41M, Exits at $242.9M

Hello (again) world!

Inspired by a post from Andrew Chen, I’ve decided to resume blogging. If I can’t find time to write while taking a year off to travel it’s probably never going to happen.

I spend a lot of time answering questions and giving advice about growth, product management, and startups, so those will be common themes for the blog. I also dug up some unpublished posts from when I was running HeartThis that early stage startup founders may find useful.

Expect new posts roughly once per week. If there’s a particular topic you’d like me to write about send me a tweet @thegad.

If you’re not 10X better you don’t matter

My last startup failed. You may read that we were acquired, that it worked out well for our investors and team, and that we’re excited about new opportunities. That’s all true, but at the end of the day we still failed. More specifically, I failed. I didn’t move the needle for my investors, my employees didn’t make life-changing amounts of money, and our product didn’t make a significant impact on the world. We had all the right ingredients — funding, talent, relevant experience — but we came up short for one simple reason: we weren’t 10X better than our competition.

At HeartThis, our vision was to create the definitive online shopping site by putting all your favorite stores in one place. When we started, the market for shopping apps was already crowded, but our team had a secret weapon: we were experts at growing consumer services to massive scale without spending money on user acquisition (massive = tens or hundreds of millions of users). Viral growth was our 10X edge over the competition, but we failed to commit ourselves to growth at all costs. Every single action item should have been prioritized in terms of ROI on growth. Instead, we wasted time on product features and improvements that created an incrementally better user experience but didn’t directly drive user acquisition. We built monitors to make sure prices and inventory stock-info were accurate. We didn’t force users to follow friends on install because user tests showed that was a turnoff in some instances. We spent significant engineering resources ensuring that users always saw new content when they returned to the app. All nice features, but all 100% worthless without a 10X differentiator between us and our competitors. That lack of focus killed our company.

When raising a Series A or later round, investors aren’t willing to take a chance on a product that has a slightly better user experience and a slightly better growth rate than the competition, which is exactly what HeartThis offered. We would have been better served by putting more effort on growth and being able to point to an order of magnitude higher growth rate than all competitors even if that meant we had a merely adequate user experience. When it comes to post-seed investing, investors need a reason to believe that your company is a true outlier because they’re looking for the handful of superstar investments that return the fund[1].

It is extremely difficult to be an order of magnitude better than your competition at one thing, but it’s fairly easy to be incrementally better at many things. This creates a dangerous cycle. You feel a sense of accomplishment for each incremental win over your competition. As a result, rather than tackling the difficult task of turning a small advantage into a 10X differentiator, it becomes tempting to search for another easy win and the pleasant sensation of steadily increasing your value proposition relative to your competition. This will ultimately create a product that is slightly better than your competition in many ways…and then you will run out of money and your company will die.

Don’t fall into the trap of incrementally better. Figure out what makes your product 10X better than your competition and ruthlessly push towards that goal. Investors, employees, friends, family, and other well-meaning people will point out all of the other things you should be working on. Record all of their suggestions, then ignore them until after you hit your 10X goal. Users don’t abandon products they’re familiar with for incrementally better. Investors don’t throw money at companies that are incrementally better. Massive success isn’t born from incrementally better. If you’re not 10X better than you don’t matter. Once you are 10X better, then you can flesh out the rest. I learned that lesson the hard way, and I sincerely hope that you’re able to learn from my mistake.

[1] For more on how investors think, see Fred Wilson’s What is a good venture return?

Finding Funding: It doesn’t count until the check clears

A lot of people have asked me about my experience fundraising for HeartThis over the last few months. We successfully raised funding from a fantastic group of investors (including Freestyle Capital, Google Ventures, 500 Startups and more), but if I had it to do all over again there are many things I would do differently.

One thing I learned is that no investment is a sure thing until the money is in the bank. You’ve probably heard this before, but it’s 100% true and important to keep in mind when pitching. I’ll cover three examples of how this can play out. Two come from personal experience, and one is a gut-wrenching example from a friend.

Insufficient funds
An individual angel investor expressed interest in backing HeartThis. We went over the details of the business, the team, and all the risks involved, and they remained solidly on board. However, when the round was closing and the time came to provide final details in order to receive financing documents I opened my E-mail to discover a message saying they had to pass for financial reasons. This is something you have to be aware of when dealing with individual angels. Often times they don’t have tens (or hundreds) of millions of dollars set aside specifically for investing, so their ability to invest is much more tenuous.

Failure to close
The HeartThis team has personal connections to a number of professional investors. We began speaking with one such individual early on. Between our personal ties and their warm reception, we were confident that they would participate in our seed round. Despite being positive towards our team and business, they ultimately declined to participate in our seed round. Losing their investment was primarily my fault. Our personal connection to this investor wasn’t through me, so I was less aggressive about following up and building momentum with them than with other investors. Instead, I let our team member with the closer connection manage the relationship. This was a mistake. Investors want to see the CEO take charge so they can have confidence in their ability to lead a new venture in the face of overwhelming odds. By playing a passive role in courting their investment I failed to instill that confidence, and I believe that ultimately led to them passing on our round.

Losing your lead
This story comes from a friend and fellow founder. Their startup was in the midst of wrapping up their Series A funding with a prominent VC leading the round. At the last minute, the firm decided that not only were they not going to lead the round, but they were not even going to participate. This put the company into a full-on crisis. The CEO went from feeling confident about raising a major round of funding to facing the prospect of not being able to make payroll the following month. They were forced to literally beg other participants in the round to not drop out and to instead consider increasing their investment. Anyone who has gone through fundraising before will recognize how terrifying a situation this would be. Most investors are followers, and they want to get in on hot deals that alongside name-brand firms. If you have a top firm back out of leading your round, the majority of other investors won’t even consider putting in money. The emotional toll on the CEO was immense, and the company came very close to disaster.

When it comes to fundraising, do not relax until the money’s in the bank. A positive feeling doesn’t matter. A verbal commit doesn’t matter. Even receiving term sheets doesn’t matter. None of them are legally binding, and there are countless examples of investors choosing not to invest (for both good and bad reasons) at the eleventh hour. Close investors as quickly as possible before they have time to cool off (consider closing in tranches!), and don’t stop actively pitching just because you think the round is filled. Good luck!

Words of wisdom from Neil Joglekar

This past weekend I was out celebrating Neil Joglekar‘s birthday. Neil’s an old friend from Stanford and the co-founder and CEO of Reel Surfer. Neil spent a number of years bootstrapping the company and paying the bills by tutoring on the side before going through YC and raising VC funding. I figured he must have learned a lot along the way, so I asked him to share a few tips as I take my first shot at starting a company. Neil got very serious for a moment (a rarity) and gave me the following advice:

Manage your emotions, and hang out with people who don’t care that you’re running a company.

I thought that was some of the best advice I’ve received thus far when it comes to entrepreneurship.

Prioritize needs over wants

As the HeartThis CEO, I constantly struggle with the conflict between what I need to do vs what I want to do. I spent most of my career as a software engineer and/or product manager, so I have a natural affinity for rolling up my sleeves and getting dirty building product. As CEO, that’s in direct conflict with my core priorities of setting the company vision, securing funding, and hiring and retaining a great team. As much as I want to slap on headphones and crank out a new feature, it’s my duty to set the team up for a long-term win. Focusing on hiring a new crack engineer who can do dev work full-time is a much higher leverage use of my time. Coding is a want, but recruiting is a need.

Similarly, while fundraising, it was painful to note the decreased speed of product development. I kept asking myself “what could we have accomplished if we spent these two months head-down building product rather than sitting in meetings talking to investors?” In reality, that was the ultimate short-term thinking. It’s true that fundraising slowed recruiting and product development down substantially, but it ultimately gave us the cash necessary to go out and hire top-notch talent.

A good leader has to learn to trust their team and stay focused on doing what needs to be done for the good of the company, even when it doesn’t perfectly align with what they want to do. I suspect this is one of the harder leadership lessons to learn for people who come from “hands-on” positions like engineering and design. I do still tend to do a small amount of dev work each week, but now it’s typically my lowest priority task that only gets addressed after everything else has been taken care of.