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I'm Jake Goldman, Founder & President of 10up. Ask me anything!

Oct. 19, 2016

Hey there - I'm Jake Goldman, and I like to say I've been "making with the web since there was a web to make."

I started making websites in the 90's when I was still in high school, taking on my first paid gig in 1997. Over the next 14 years, I worked in the technical and creative services industry as a developer, designer, manager, and salesperson... usually wearing several of those hats at once. I've worked for huge organizations (the U.S. Navy) and tiny organizations (employee #2 at my last job). I went through the first browser wars, built interactive applications in Flash when that was a thing, spent too much time working with a proprietary ColdFusion CMS, and even "designed" a few web ads (yikes).

In February of 2011, I started a consultancy focused on WordPress engineering and UX called 10up. While I had ambitions to grow (I didn't call it "Jake, Inc."), having spent the last 5 years in senior management, I thought it would be nice to take a year off from managing teams and focus on projects I could handle as a freelancer, maybe collaborating with a few contractors. I'm bad at saying "no" when opportunity knocks, and before 10up's first year was over, I'd grown the team to 8 employees, with some noteworthy showcase clients, like TechCrunch and Trulia, already under our belt.

Since that first year, 10up has organically grown in size and scope. Today, we are ~130 full time staff strong and as financially healthy as ever, with expertise spanning virtually every aspect of making and supporting even the most complex and high scale web projects. Our expertise goes much deeper than WordPress (still our preferred CMS), and includes user experience and creative design, monetization and advertising strategy, front and back end engineering, and of course, project strategy and management. Last year, we had a client project featured on Google's home page (it uses the WordPress REST API, and yes, it stayed up), and saw 4 client projects nominated for Webby Awards (AMC.com won). Since mid-2015, we've helped Adobe relaunch 99u, helped Microsoft launch Windows 10 with an official media and consumer launch microsite, collaborated with ESPN to release another flagship property (The Undefeated), helped both the New York Times Co. and Washington Post with some publishing tool projects... and the list goes on. An analysis of the impact of iOS 9 Content Blockers that I co-authored was featured and quoted in publications like Time, AdAge, and Daring Fireball.

I'm also very proud of 10up's continued tradition of investing heavily back into in the open source platforms we depend on. We're the only agency that employs a Lead WordPress (Core) Developer, likely the largest contributor to WordPress behind Automattic, our company plugins are listed as "active" on ~1 million WordPress installs, and projects like VVV and Flexibility have become standbys. Our team has spoken at events around the world: phpWorld, NTC, ZendCon, CSSCONF, Gilbane, and of course, anchor WordCamps like U.S. and Europe - to name a few.

The journey has been inspiring... and exhausting, exhilarating, emotionally draining, and unbelievably educational and maturing. Even in our toughest moments, or when I'm agonizing over a mistake I've made (in classic type-A fashion), I've always tried to keep perspective, and remember just how fortunate I am, both professionally and personally.

These days, when I'm not working with team 10up, I'm usually chasing around one very curious 10 month old daughter. In the event I get a bit of independent free time, I've been cultivating an interesting in cooking, and indulging a home-automation interest. My podcasts playlist consists mostly of political and issue commentary, with a sprinkling of Apple enthusiast news. I do enjoy a good Netflix original, but with my new daughter in the picture, a "binge" looks like finishing one episode without interruption. I'm eager to travel more, again, when I can.

Ask away!

Comment
33 votes   Flag
Dodgers Benny

Would you rather fight 100 duck-sized horses or 1 horse-sized duck?

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Jake Goldman

Definitely 100 duck-sized horses. A horse-sized ducks sound terrifying.

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Dodgers Benny

Everyone usually says 1 horse-sized duck. I don't understand it! You have the right answer, it DOES sound terrifying.

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Bill Dennen

Congratulations on the success of 10up!

What advice would you give your 2011 self? or your 1990s-era self?

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Jake Goldman

2011 self: make more time to develop personal/professional relationships with valued colleagues and nurture team culture. In hindsight, I can understand why, while working some very long days, I tended to give short shrift to deeper conversation and the "softer" with my team, but that calculus was ultimately a mistake.

I wouldn't even know where to start with my 1990s self! Perhaps, "do fewer things, and do them well" and "express gratitude." I still sometimes struggle with a tendency to overburden myself to the point where quality struggles, but that habit was at its peak in the 90s. I was also pretty awful when it came to acknowledging and appreciating others contributions to my development and success; fortunately, I had close friends and family that forced me to confront this personal shortcoming.

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Vladimir Prelovac

Hey Jake

Glad to have you here. Got a ton of questions for you :)

- What's your second most liked CMS?

- Do you deploy vanilla or modified WordPress ?

- How does a web agency land Techcrunch and Trulia as clients in its first year?

- How do services of this type scale? Would increasing your revenue 10x require adding roughly 10x more people to your team?

- Have you ever thought of your own conference dedicated to web professionals out there?

- What is your greatest challenge nowadays?

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Jake Goldman

Thanks for having me here, Vladimir!

"What's your second most liked CMS?"

At this point, I'm largely familiar with the major CMS options (SiteCore, Drupal, Adobe Experience Manager, etc) and a few more niche platforms that we've encountered, and in many cases, I'm not as intimately familiar with those choices these days as some other 10uppers. That said, my instinctual "go to" is Drupal (though I haven't personally built a site with it since Drupal 6), insofar as I like its (new) Symfony underpinnings, and appreciate its WordPress-like commitment to open source and community.

"Do you deploy vanilla or modified WordPress ?"

Can you clarify? We don't modify WordPress core, if that's what you mean, nor do we have a default "distribution" that's different than WordPress core that we start with. We do have a number of reused plugins and modules that are shared between similar clients.

"How does a web agency land Techcrunch and Trulia as clients in its first year?"

While 10up was around for less than a year, it's esteemed founder ;-) had been around the web development block for over a decade, and was actively involved with WordPress development (including core contributions) and its community for roughly 3 years. That is to say, the connection and introduction was really to me (personally), through contacts and relationships I'd personally nurtured and developed for years, who were familiar with my work. That, and when I land a compelling lead, I chase it aggressively!

"How do services of this type scale? Would increasing your revenue 10x require adding roughly 10x more people to your team?"

I'm going to come back to this question later in the day (when I have a bit more time), as I think it merits a longer answer.

"Have you ever thought of your own conference dedicated to web professionals out there?"

10up has an annual summit that brings together all of its employees, and is at least 60% educational material that could benefit anyone in our space. I've briefly pondered the idea that we could extend that event - more explicitly breaking out the culture and corporate parts more specific to our team - and open it to a larger audience. We're not prepared to do that right now or in the immediate future, but it has crossed my mind.

"What is your greatest challenge nowadays?"

Two summarized answers. (1) As 10up gets larger, ensuring that every member of this team - from new engineers to senior leadership - still feels a sense of urgency and commitment to every one of our customers; that we don't follow the well worn trend of a larger company becoming less "energetic" and "capable" as it gets further away from its leadership. (2) Managing my time: with so many irons in the fire, and increased family obligation (since the birth of my daughter), assessing what I can make time for and what I can delegate effectively is a persistent challenge.

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Jake Goldman

"How do services of this type scale?"

There's more than one way to scale, though I personally advocate for growing service businesses with negligible material costs through organic growth.

The short version is, figure out how many "hours" (even fixed fee or - shudder - "value" pricing still should have an hourly estimate of time underneath it) you need to sell in order to cover the total cost of employment of a new hire, figure out a margin you're comfortable with on top of that, and - assuming you want and/or anticipate growth - hire at that point. When you do the math, depending on what your charge (and assuming relatively modest-to-standard consulting rates), it turns out you probably only need to be comfortable selling somewhere between ~30%-50% of someone's time to be at breakeven. As a bootstrapped founder, depending on what you're comfortable earning as minimum, when you've booked yourself up to ~40 hours of work per week, you should be pretty comfortable hiring employee #2. That math becomes easier as you grow, as the amount you need to be overbooked "per capita" increasingly goes down.

"Would increasing your revenue 10x require adding roughly 10x more people to your team?"

Leaving diversification into productized solutions off the table for the time being, it is a fair over-generalization to say that growing *total revenue* requires growing the number of hours you're selling, just like growing the number of units you're shipping is required to grow a material product business. I think we sometimes over think the difference between services and product business at the macro level: in a service business you're still "shipping a unit", it just happens to be people's time.

The economies of scale, particularly around *margin* are different, but even then, it's a fallacy to imply that a service business doesn't also have economies of scale (even if they can't touch the economies of scale of *digital* goods that can have extremely low marginal costs). My accounting and tax costs were roughly the same at 60 people and 120 people. I needed full time HR support with just 15 employees, and even as we grew to 8x that, we've only increased HR spending by roughly 2x. Many software products (and even hardware providers) offer volume discounts, enabling us to spend less per capita as we grew. Scale lets our team sub-specialize, which returns in the form of comparative quality and efficiency advantages. To be a leading open source contributor at just 20 people, the investment as a percentage of our revenue is very high; at 130, we can stand even further above the crowd while spending less as a percentage of our revenue.

I also want to address something my friend Shane said in a recent AMA, where he pointed out that team growth / scaling an agency doesn't grow your margin, because I think there's a critical nuance that can be lost in that. It is true that your profit margin - the *percentage* of revenue assigned to profit - historically decreases as you scale a services business (more moving parts / people is more costly - I don't have to have meeting with myself, as a freelancer, for instance). However, the total profit - in real dollars - can absolutely increase. Put plainly, 10up's margin (percentage of revenue assigned to profit) is considerably lower than it was during the short period when I was a one man show. But I (am fortunate to) do considerably better than I did in my first year of 10up, because our total revenue is astronomically higher, and even if the percent assigned to profit is smaller, the total pool is much larger.

Put another way, profit per head at IBM or Edelman or RGA is likely much smaller than some of my very talented freelancers, but I'd wager their executives and owners are doing much better for themselves. ;-)

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Jimmy Blanco

Jake,

We love Managewp. Dashboard for all our sites have been a blessing. Have you found anything that will incorporate the magic of managewp with error logs?

When we updated plugins/themes/Core via ManageWP, we cross our fingers hoping that nothing breaks.

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Jake Goldman

I don't know of a solution that serves both of those use cases (site management, stack troubleshooting) very well. We use New Relic for advanced troubleshooting and alerts within our stack (including error logs), and we're working on some deeper integrations with WordPress that we currently plan to open source.

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Ryan D. Sullivan

Jake,

Two questions:

Best decision you've made since starting 10up?

Hardest decision you've made since starting 10up?

Thank you!

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Jake Goldman

Both answers represent two sides of the same coining: team cultivation / development.

Without naming (too many) names, there were some key senior hires we've invested in - I'll list our CEO John Eckman as one example, since he's doing an AMA with you soon - that I can barely imagine operating without, today.

On the flip side (and definitely not naming any names), we've welcomed some incredibly bright, capable, likeable - sometimes fairly well known - individuals into our team who we clearly struggled to effectively operationalize internally. The decision to part ways with very smart, often likeable people who aren't working out at 10up is always agonizing - even when it's the right choice.

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Nemanja Aleksic

At which point do you decide that it's not working out?

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Jake Goldman

That varies from case to case, and I'm not sure I can offer a good universal rule of thumb.

Broadly, when I'm confident that we've done our part - within reason - to (1) set him or her up for success, and (2) provide an opportunity to correct, and I'm not seeing a change.

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Omaar Osmaan

Hi Jake, great talking to you- :)

(1) What do you do to avoid any burn-out from day to day work stress, or disappointment/disagreement between action-plans vs outcome?

(2) Regarding partnership, skill-hunt and negotiation- what are your tips?

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Jake Goldman

(1) Disinterest and boredom, more so than stress, burns me out. Having a plan to continuously "grow out of" assignments on my plate - through mentorship, delegation, hiring - keeps me going. With so many projects, investments, and staff, some steady trickle of challenges, frustrations, disappointments, and disagreements is inevitable. I don't want to say I'm "numb" to them - I take every problem seriously - but I suppose I want to say I've embraced the idea that it's my responsibility - maybe even my privilege - to help confront those. The trick is to keep them in perspective: remembering that ultimately, while the "problems" may consume in outsized share of my time as President, they represent a small fraction of the impressive work that 10up is doing every day. Of course, you also need to force yourself to find discrete time "away from work" every day and every week.

(2) I could write a book answering this! I'll try to summarize by saying that empathy and a genuine search for the win-win scenario are the foundation of those relationships.

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Omaar Osmaan

Thank you so much for the answers. It's refreshing to know "having a plan to continuity" (having the plan itself is important, otherwise things feels boring) is your thing, too- usually, I find many people surprise of the behavior!

Absolutely agree on the summary, empathy and finding win-win scenario seems the the solid base for all of these- would love to see you write a book about it, someday perhaps.

Thanks again.

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Nemanja Aleksic

Thanks for being on our AMA!

10up employees have dedicated a lot of time to WordPress community involvement, which is pretty impressive given the disproportionately low number of employees when compared to other top contributors. What's the company's stance on this, and do you have any rules regarding this matter?

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Jake Goldman

Our stance is pretty straightforward: we think contribution is "the right thing to do" (we've succeeded, in some measure, on the backs of those who volunteered before us), and smart business, insofar as that leadership attracts other leaders to the company and makes for a pretty compelling pitch when explaining our expertise.

We have, increasingly, sought to encourage contributions more through the lense of opportunities and discoveries that arise in the course of engaging with clients (real world problem solving), rather than an abstract donation of time (though we still do some of that, too).

I wouldn't say we have any hard and fast "rules." We have policies around proposing community contributions, and of course, being careful about distinguishing "working for hire" from something 10up owns and can "give back" without permission (vis-a-vis plugins / extensions in particular).

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Clifton Griffin

Jake,

Thanks so much for sharing your knowledge. Your answer on the 10x question was so illuminating. As an owner of a small agency (3 of us!) scale is constantly a fear.

My question is: how did you decide to hire your first project manager, and related sales employee? How big was your team?

Hiring developers is (relatively) easier for me to justify math wise. Would love your thoughts!

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Jake Goldman

Realized I didn't answer the second question: we hired our first dedicated "sales" employee when we were ~20 people (our project managers lent me a hand before that). I did so at the point where it became very apparent that I had more on my sales plate than I could handle. I was probably over cautious about that hire, myself, since the math for a sales hire is trickier; typically, they have to sell ~8-10x their total cost of employment, just to break even. It took losing a few deals that suffered for my time and energy to make the leap.

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Clifton Griffin

Wow, I would have never thought it was that high of multiple. Thanks again for all of your insights.

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Jake Goldman

Our first project manager - now our VP of Client Delivery - was one of our first 5 hires. A typical rule of thumb for project management is ~20% of a project's cost; so with 4 engineers, the need for 1 time full time project manager was very apparent and felt. As with most good early hires, I was fortunate to find a "chief project manager" who was also comfortable wearing many hats, which sometimes looked like content or marketing strategy for clients, and often looked like support and back up on sales and marketing.

But perhaps more to the point, good project management is critical to the success of any engagement, and I knew (from day 1) it was neither the best use of my time nor what gets me out of bed in the morning. I was very confident that allocating ~60% of my time to business development, rather than project management, was a no-brainer in terms of ROI. Fiscally, but I also put a high price on my sanity, if you can call it that :-P.

To riff a bit more here, I think there are two other personal philosophies this exposes:

(1) An innate appreciation for opportunity cost, or as engineer, perhaps efficiency: it's not what I *can* be doing, or even necessarily what I *want* to be doing; the question is what's the *optimal* use / best ROI on my time?

(2) There's a hard to quantify "return on passion" (ROP??) that I believe in. Which is to say, when someone is excited about their work, it tends to be *much* better. You can't just say "what's the ROI on working on A or B" as if a human being will execute both with the same passion and fervor. Even if a robot performing both tasks equally would mean option A yields more ROI, a human being bored to death by A but incredibly passionate about B should be assigned B.

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Ahmad Awais

Hey, Jake!

Huge fan of 10up's work. Your journey sure does sound pretty incredible and a complete emotional rollercoaster (If I may add).

Here're a few questions that I think a person in your position can answer best.

Q#1: Even before reading your bio/summary, I knew I was going to ask this question but when I read the roles you've been in "developer, designer, manager, and salesperson... usually wearing several of those hats at once" I knew I should def ask this one. So here it is...
— I have been deeply involved in the WP community, which is why I know for (maybe a fact) that it is hard to get promoted. As it is in the current state of known WordPress agencies (maybe it's the speed at which tech stacks are changing, or maybe it's hard to get promoted from solo/lead to manager or a director level position unless you're a foundational stake owner). Which is why I see folks changing their employers — for the sole purpose of getting promoted per their improved skill set (every two years or so). I'd go as far as to say, how do you, at 10up, address this stereotype (not my words) → "There isn't much room for vertical growth or promotions - more or less you stay doing what you were brought on for in the long haul."

(Full disclosure, I have had asked this same question before from Shane at ModernTribe, so, it would be great to get your perspective on this one)

Q#2: JavaScript & its frameworks are changing pretty fast. Do you have a personal favorite, ReactJS, Angular? Vue? —— And why?

Q#3: Since you were involved with the web from 90's per se — by any chance were you involved with WHATWG Group? Or did you back W3C at the time?

Q#4: How do you hand over the projects to your clients, is there a client education phase/process? Who handles that and how/why?

Q#5: I hope to not hit a nerve here, but as an outsider, I/we all hear about the fact that working for 10up is much more resource intensive for devs as compared to a few other agencies in the same ring. Is that true? If so, why is that? Or What does 10up stand for the terms like "Company Culture" and that notorious "Work/Life Balance" (Sidenote: I don't believe in the later).

Looking forward!


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Ashiquzzaman Kiron

Hi Jake,

What advice would you give to someone who just started their WordPress journey ? Any tips ?

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Loginizer - Raj Kothari

Hi Jake,

What is your age now and what was your age when you started ?
Have you ever got tired of the tech industry ?

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Armando Duran

Hi Jake,

I just found this post and since I recently met you at WordCamp Sacramento where I had a good chance to chat with you for a bit. You may remember that I mentioned to you that I work for a non-profit remote for now and that the reason I joined them was value based more than money.

I really liked the concept of ROP, never thought about it before. And I also enjoyed reading some of the other questions and answers here (so far). I think that the fact that 10up gives back to the open source community is pretty inspiring.

My question is: what would you say at this point in time in your life, is living a meaningful life?

Keep "up" the good work with 10up!

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