26 Tips on Management, Marketing, Hiring and Productivity Told in AMAs

Danny Schreiber
Danny Schreiber / Published March 20, 2014

It’s where Bill Gates gives out personal finance advice. Where actress and entrepreneur Felicia Day admits to experiencing self-doubt every day. Where Intel CEO Brian Krzanich shares leadership lessons.

The place where this all happens isn’t some exclusive event or paywalled website, it’s a Reddit AMA (Ask Me Anything), a free-for-all forum to ask notable, unique and interesting individuals, well, anything. In recent months, I’ve discovered buried among the anything — both on Reddit and on Inbound.org's AMA category — are golden nuggets of business tips on topics from hiring to marketing to management.

“I like the idea of questions generated from the crowd,” says Dan Drabik, the creator of Interviewly, a site dedicated to showcasing Reddit’s most popular AMAs. “I think it leads to a diverse set of questions, instead of the same 4 or 5 questions that interviewers typically ask.”

But finding the best bits of advice among the many questions asked can look overwhelming with some AMAs exceeding 500 comments. So to give you a glimpse of what you may be missing out on, we’ve put together a list of 26 business tips extracted from AMAs with entrepreneurs and executives.

These tips have been categorized in five areas:

To read the full AMA, just click the link next to the subject’s name. (Note: Questions and answers are presented unedited from Reddit, Inbound.org and Beta List.)


Dharmesh Shah, Co-Founder and CTO of HubSpot - Inbound.org AMA

What were the three biggest surprises you and your team found in growing HubSpot? What aspects of starting, growing, and scaling your company diverged the most from your initial business plan and your own expectations? - Matt Gratt on Inbound.org

Big surprises:

  1. How important company culture is. In the early years of HubSpot, the word culture was never mentioned, and we didn't give it much thought. Now, I spend hours and hours (and hours) pondering culture.
  2. How much capital we've raised. (We've now raised over $100 million). I knew we'd likely raise some capital, but had no idea it would be that much capital.
  3. How much conventional wisdom on how to operate and grow a company is flat-out wrong. (More coming on this topic on my blog in the next week or so).

Having said that, I'm most surprised by how few surprises there have been.

Ryan Holmes, CEO of Hootsuite - Reddit AMA

As CEO you most likely have a lot of things on your plate - various requests from various departments.

  1. How do you prioritize what needs to be done and manage expectation of various people in various departments?
  2. How do you maintain a 'balance' between your personal and professional life? Is there one at all?
  3. What keeps you motivated and going day in and day out? - DarkBrownShoes on Reddit

My earlier business' helped me to become a generalist, and I think that is very valuable as a CEO. You need to know a little about everything (and a lot about one or 2 things). 1) It's round-robin, and by relative importance. 2) I have been working on that. Yoga helped me a ton. Right now is an amazing time, and I want to sieze the opportunity in front of me. 3) Motivation is to get a huge win for my team.

Hiten Shah

Hiten Shah, Co-Founder of Crazy Egg and Kissmetrics - Inbound.org AMA

What do you consider your biggest mistake or largest oversight during your time with CrazyEgg and Kissmetrics? - Brad Knutson on Inbound.org

Early on I didn't appreciate the positive impact of adding experienced people on our team.

Gary Vaynerchuk Co-Founder and CEO of VaynerMedia - Reddit AMA

What does culture mean to VaynerMedia and what are some of ways it's expressed, stewarded and carried out? - erdle on Reddit

Company culture is the backbone of any successful organization. To me I'm less focused on the tactics of creating it and carrying it out, and more focused on it as a concept. Company culture is a religion, not a sermon.

Ben Lerer, Co-Founder & CEO of Thrillist Media Group - Reddit AMA

Have you made any non-sexy or at least less common business decisions that have panned out really well? What were they? Something where perhaps other people disagreed with you but you did it anyway? - carl0svalle on Reddit

we make non-sexy decisions every day. i actually think the only sexy decision we made was buying jackthreads, but that wasn't even sexy at the time. sexy business decisions are generally bad business decisions. the jt move was definitely met with a ton of skepticism but everyone pretends they loved it from day one, since its worked out.

Brian Krzanich

Brian Krzanich, CEO of Intel - Reddit AMA

If you had to pick one thing - what do you believe to be the mark of a great leader? One that motivates their people? - thystrife on Reddit

to say a great leader simply motivates their people is true.. but too simple… sure every great leader has the ability to motivate people.. but… that alone is not enough in today's world… you have to be able to create and then articulate a vision.. motivated people with no clear direction… is not a winning team.. the vision to strategy piece is very important… and then… you have to be able to get things done.. to build a product.. or have people around you who can.. many of the greatest leaders have had just that.. the ability to motivate, create a vision, build a strategy… but then use teams to actually build the product..


Hiten Shah, Co-Founder of Crazy Egg and Kissmetrics - Inbound.org AMA

How should seed-funded startups think about allocating marketing budget? Are their paid channels that you advise startups try in the early stages? - Dharmesh Shah on Inbound.org

For seed-funded startups, it's usually the case that budgets are still very tight, so you probably only have experimental budgets for paid channels. I'd first focus on organic channels such as twitter or facebook that make sense for the business based on the audience the business is trying to attract. Then I'd start experimenting with paid channels to see if a reasonable CPA can be achieved. This usually means spending $1000 - $5000 per channel to test to see what the CPA looks like. Right now, I'd suggest Twitter Ads, Facebook Ads and have seen people successful with AdWords too.

Kevin O'Connor, Co-Founder and Former CEO of DoubleClick, now CEO of FindTheBest - Reddit AMA

What marketing strategies do you normally use? - Guacamole_Soldier on Reddit

Best marketing lessons I learned from Lee Nadler who ran DoubleClick marketing:

  1. businesses are consumers
  2. brand is about delivering on the promise

We tend to focus on #2 - help people make quick, informed decisions.

Oli Gardner

Oli Gardner, Co-Founder of Unbounce - Inbound.org AMA

Since you're basically the best blogger ever (or at least my favorite) I'd like to see if you can expand on this as far as the actual content of the blog posts you write. What are 3-5 things that you believe every incredible blog post needs? - MyCool King on Inbound.org


  1. A strong opinion. I want to feel like an author is taking a stand, and actually daring to lead me.
  2. Entertainment. If an author bores me I'll never come back to read their posts again.
  3. Original visuals. If someone cares enough about a piece of content to create beyond the copy that's a big signal of someone who gives a ****. That's one of the things I love most about your posts Mike.
  4. A single overarching takeaway. By reading this post, you'll learn exactly this.
  5. Love.

Patrick McKenzie, Founder of Kalzumeus Software - Beta List AMA

What are your top 3 tips for startup entrepreneurs trying to bootstrap their marketing / PR - Chris Duell on Beta List

For PR, you need to a) make personal connections with journalists and b) pitch basically pre-written stories which insert yourself into something that they already want to write about. You might notice, for example, that a lot of reporters transparently want to write stories about income inequality, the terrible hiring market, etc etc. If you're Airbnb, you pitch reporters on "Hey, the sharing economy is a great way for tech companies to not just benefit rich white/Asian tech entrepreneurs. Here's an easy layup human interest piece about people saving their houses from being taken away due to using these 3 sharing economy companies."

Joel Spolsky, Co-Founder of Stack Exchange and Fog Creek Software - Reddit AMA

How much of the success of FogBugz (or Fog Creek) do you attribute to the ancillary marketing benefits of publishing Joel on Software? In other words, how successful would that product be without your personality behind it? - amoore on Reddit

It was 99% of our marketing at first, so it was just super-critical. After a few years, our products were well enough known on their own merits that Joel on Software wasn't necessary (stopping the blog did not reduce our sales).


Dave Girouard, Former President of Google Enterprise/Apps, Founder of Upstart - Reddit AMA

Best advice to give someone about business? - bobmuluga on Reddit

Don't let fear keep you on the safe path. And always give back more than you take.

Dharmesh Shah

Dharmesh Shah, Co-Founder and CTO of HubSpot - Inbound.org AMA

They say focus on one thing and do that one thing amazingly well. HubSpot had to buck that trend by being an "all you ever need" package. What advice would you give for building a totally bootstrapped startup in the same "we might have to do everything/lots of things to be viable" ? - Ed Fry on Inbound.org

Candidly, I would not generally recommend HubSpot's approach (trying to build an "all-in-one") as a bootstrapped startup. There are a fair number of challenges with that broad strategy – one of which that it's a much more capital intensive path than the alternative. In our case, we ended up raising over $100 million to pursue that ambitious strategy. That's a lot of money.

So, this is one of those cases where the conventional wisdom (focus on one thing and do it well) is generally good. My thinking here is that you start with something narrow and well-defined, and then broaden out the scope over time based on feedback you get from users/customers.

Ryan Hoover, Co-Founder of Product Hunt - Reddit AMA

When you were in the initial stages of planning/developing your application, did you ask for outside advice, and if so, how did you keep your idea secret so that it couldn't be Zuckerberg'd by someone else? - timmyblob on Reddit

I don't worry about people stealing my ideas. Ideas are thrown around all over the place and frankly, most people don't care about your "genius" idea. It's better to be transparent and gather a lot of feedback from the community and smart people.

The best feedback we've received is from the community themselves and their actual use of the product. But I've also had incredibly valuable conversations about Product Hunt with kickass entrepreneurs like Josh Elman, Nir Eyal, Hiten Shah, Kevin Li, Ben Yoskovitz, Ash Bhoopathy, and many others (thanks, guys!).

I see too many founders/product builders not ask for help or advice. Mentorship and guidance from more experienced entrepreneurs can save a lot of wasted effort.

Bill Gates - Reddit AMA

What is your best personal financial advice for people who make under $100,000 per year? - anonymouslives on Reddit

Invest in your education.

Felicia Day

Felicia Day, Co-Founder of Web Video Network Geek & Sundry - Reddit AMA

I was wondering if at any point in your career did you ever doubt yourself during low points–along the lines of, "I love this thing, but am I truly cut out for it?" Do you have any advice on how to push over the "self-conscious" side, and just make things? - PythonScyther on Reddit

I experience self-doubt every day! When I start to really fall back I start journaling a lot and find that a lot of the self-doubt is just a voice that doesn't want me to succeed in my head. That voice is not my friend, so I am able to separate it, silence it and keep going!

James Altchur, founder of 20 companies (17 of which failed) - Reddit AMA

Do you have any tips for someone going into the business world? What type of degrees would be nice, what colleges in the country are nice, etc? I heard the business world was tough but very rewarding. Please share how early life was for you when you were starting up. - hytrah on Reddit

Forget everything in your question. Forget these words: "business world" , "degrees", "colleges", "tough".

Here's what you do: every day try to figure out ten ideas that will create value for people. You need to build the idea muscle or it atrophies like any other muscle. School doesn't do that. School atrophies your brain.

Don't expect your ideas to be good. After about six months they will start ot be good. Become an idea machine. help people. Eventually charge people to help them. Now you are in business.

Take a fulltime job so you can get paid while you are building your idea muscle.

introduce 2-10 people a day to each other who you think can help each other. Build out your network this way. Deliver value.

That is your schooling. Nothing else will ever work.

Matt Mullenweg

Matt Mullenweg, Co-Founder of WordPress and Automattic - Reddit AMA

I was wondering what advice you have for people looking to start a profitable business, without sacrificing the ideals and values that motivated them to do it in the first place? - shelob9 on Reddit

It's really hard not to be distracted by the things you think you should be doing, or that you see other businesses doing, and focus in on what actually matters to your chosen business day in and day out.

It's easy to be very busy but not get anything done that you'll look back a year from now and say was worthwhile.

It's good to work someplace before starting something on your own.

If you can bootstrap without investment you'll have more control. But make sure you'll drive yourself to higher and higher performance and growth the same way someone external would.

You'll get a lot of contradictory advice, and often neither side is wrong.

Kevin O'Connor, Co-Founder and Former CEO of DoubleClick, and now CEO of FindTheBest - Reddit AMA

My goal is to found a startup in the next couple years, but I currently work at a small tech company in Chicago where I am an early employee (<3 people). I want to leverage this opportunity to really prepare myself for when I start my own company, so what experiences should I try to get or what things should I do to best prepare myself for when I found my own company? - alexlumley on Reddit

It depends. If you are an engineer, I would spend a lot of time becoming a great engineer - code, design, solve problems, etc. Most successful tech CEOs where extremely proficient at their craft. I spent 10 years coding at my first startup and didn't manage anybody until I was 30.

Otherwise, the best thing to do is to grab responsibility. With 3 people, the first one to initiate something usually owns it. Jump in, make it happen.

Noah Kagan, Founder of AppSumo - Inbound.org AMA

How do you approach the topic of passion (e.g. all I want is to be teaching yoga, making music, etc.) with market opportunity? Should you build what the market needs or just screw it and create what you love? - Steve Haase on Inbound.org

I personally have always made the most money and stuck with projects when I solved my own problems. You can call it passion or just trying to create something you want to see exist in the world. Makes it much easier to persist when times get tough and they always get tough regardless of companies success.

Tech Conferences: http://okdork.com/2010/09/01/how-we-made-over-100k-doing-tech-events/

AppSumo and now SumoMe (free tool I use for my personal blog, okdork.com)

There are two caveats I'd encourage you:

a) Validate that people also want the problem you are solving. I tried to get friends to pay for me to take them on taco tours, no one wanted it but then I changed it to a Craft Cocktails event and sold 25 tickets within an hour, see here.

b) If you are dead broke and don't LOVE your idea which is a common wantrepreneur excuse I encourage people to just start any business that makes money ONLY as a learning experience.


Noah Kagan, Founder of AppSumo - Inbound.org AMA

Could you share some tips on how you recruit marketers for your team? Where do you look? What do you look for? What does the interview process look like? - Dharmesh Shah on Inbound.org

I wrote this article on how to hire a good marketer.

But the TLDR is really this:

  • Go to the sites like inbound, conversionXL or growthhackers and see who's doing / commenting / writing things that aren't full of shit.
  • Look at marketing that is working on you and find those people via LinkedIn: who's writing the great content at Kissmetrics, which creative campaign happened from HowAboutWe or have solid thoughts about marketing like my buddy Brian Balfour.

The best people to hire are generally already employed so you have to be proactive on meeting them before they are ready to leave.

Also, it's great to host meetups online / offline to start building your relationships with people you may want to work with in the future. I hosted a conversion meetup at our office and had the great chance to meet Roger Dooley, Peep Laja (who's already buddy) and the Eisenberg brothers

As I've grown my business and age I worry / realize I won't always be relevant so you have to pay / hire people who are up to date with the now (ie. they are actively on sites like Inbound) and be humble with what you can learn from them.

Joel Spolsky

Joel Spolsky, Co-Founder of Stack Exchange and Fog Creek Software - Reddit AMA

You have a very aggressive interview process. What are your feelings on self-taught developers? Do you only hire devs with Computer Science degrees? - Chippsapoloosa on Reddit

I don't care if someone has a computer science degree… I don't think it is much of a predictor of programming ability.

How does the self-taught crowd make it past your screening process? You've stated you look for exclusivity (people who went to Yale and are israeli paratroopers was your example, I believe?) in people's resumes. Seems like people without a degree wouldn't make it here. - omglolwtfbbq on Reddit

What we're looking for is evidence that someone else has judged your work and found it to be awesome. That doesn't mean getting a CS degree.


Felicia Day, Co-Founder of the Web Video Network, Geek & Sundry - Reddit AMA

As a business owner, how to do you decide what to delegate to others and what to handle yourself? - Theothia on Reddit

This is the best question! It's been the hardest learning curve for me, how to scale. Before G&S we never had an employee, now we have awesome staff but it's hard for me to not say, "I'll just do it myself." I took time to write down all the things I LOVE to do and what I do BEST and now I try to take a pause every time I do something and ask, "is this on that list?" Because everything takes time and has opportunity cost. I'm not there yet but it's definitely a move in the right direction.

Leo Widrich, Co-Founder and COO of Buffer - Inbound.org AMA

How do you (and Joel for that matter) manage to stick to the same daily routine? Any tips would be most appreciated. - Mike Abasov on Inbound.org

I think the key to a good daily routine is to have a great environment. I think Jim Rohn's quote applies: "You are the average of the 5 people you spend the most time with."

This is something that I believe makes all the difference of whether you can stick to a daily routine or not. I discuss my routine a lot with Joel and Joel actually has a much better focus still on developing routines and habits, so naturally I'm pushed a lot and motivated through this. Finding others who also have an interest in a great and productive routine really is probably 80-90% of what you can do to set yourself off on the right track.

The other thing I would say is to follow another great piece of advice from Joel which is "let yourself be sloppy".

I think when you start out with your own new habits and routines, don't be too strict with yourself. If you get 3 out of 5 days with your new habit, that's great, celebrate that. And work towards 4/5 and then 5/5 for example.

Hope that helps to start things off! Of course, reading zenhabits.net is another great way to get inspiration!

Noah Kagan

Noah Kagan, Founder of AppSumo - Inbound.org

How do you (personally) decide what to outsource and what to do yourself? Basically how do you know when a task is something only Noah should take care of right now? - Kevin Marshall on Inbound.org

OMG. What an awesome question. Spent 3 hours discussing this with my brother this weekend. I think it's good to do "grunt" work yourself so you can stay sharp. I've gone through a pendulum where I had my assistant do everything and then she quit and I ended up doing everything myself.

It really comes down to personal preference. As of now I have a part-time assistant who'll help with locating supplies for the office, scheduling some meetings and make reservations, etc… I also actively use Burpy / AskFavor and Taskrabbit for things like delivering food, taking things to post office or picking up things like my laptop at the Mac store.

For business I HIGHLY encourage everyone to do all the work in the beginning themselves. For AppSumo I did the coding, support, business development and marketing. Then overtime, I cherry picked the work that was most fun and hired people who could do the work better than I can.

It's hard to say the exact formula for what to outsource. It comes down to what do you value vs the cost it takes you. Ie. My brother likes to mow his own lawn vs hiring a gardener even though he can afford it.

My biggest suggestion is to try it out. Hiring / outsourcing / insourcing is a mindshift that takes time to get comfortable with and see the results. Then you can decide what kind of balance works for you.

One secret thing I learned this weekend is Visa Concierge, it's basically a free assistant. My brother uses them all the time.

What business tip have you found helpful from an AMA? What's your favorite AMA of an entrepreneur or executive? Please share in the comments below.

Credits: Hiten Shah photo via clubic.com, Brian Krzanich photo via Intel, Oli Gardner photo via Twitter, Dharmesh Shah photo via HubSpot Felicia Day photo via Google+, Matt Mullenweg photo via ma.tt, Joel Spolsky photo via LNETM on Meetup and Noah Kagan photo via OKdork.com.

You might also enjoy this article: "From 0 to 100,000 Users in 4 Months: The Story Behind Productivity Chrome Extension Momentum"

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