Ian Landsman

Founder & Dev. HelpSpot / Larajobs

A few weeks ago we completed our fourth installment of Laracon Online. An annual fully online conference for the Laravel PHP framework and related technologies.

Each year Laracon Online has over 4,000 paid attendees from over 100 countries.

The event has been both a commercial and community success, with great NPS scores and profit margins around 70% (click below see comments by attendees):

With the rise of COVID-19 and the cancellation of so many significant events it seemed like the right time to write up how we pull off Laracon Online and how you can do the same.

Every community and conference is different. Not all of this may apply to your specific situation, but I've tried to break up these ideas into logical chunks so that you can use what works and discard what doesn't.

If you find this useful for your event, please let me know on Twitter.

Why an Online Conference?

Coronavirus has made clear some of the distinct advantages of an online conference. Everyone from attendees to speakers to showrunners can participate from the comfort and safety of their own home.

There's so much more than that though. What initially drew us to the idea of Laracon Online is it was a way to give a much larger audience the experience of going to a fully realized Laracon.

Even in less severe times, there are many reasons why people can't attend conferences.

Most obviously, in-person conferences tend to be very expensive. They require a lot of people, venue, food, security, all of those costs are passed along to the customers in ticket prices usually approaching $1,000 or more.

Beyond that, there's the expense of traveling to the location, airfare, hotels, food, missed work. I've rarely been able to attend a conference for less than $2,000 and sometimes it's far more.

An online event not only lowers the cost but also helps those who may not feel comfortable at a large in-person conference, as well as those who may be physically disabled and could not otherwise attend.

In-person conferences also tend to self select down to a particular country or region. An online conference creates an event open to the whole world. At Laracon Online, we've never had less than 110 countries represented at the event. You won't find that kind of worldwide representation at an in-person conference.

Production Crew

An advantage of running an online conference is it takes far fewer people to pull off. We run our 4-5k person event with only two people on show day.

I manage organizing sponsors, speakers, and MC on show day. Eric Barnes of Laravel News runs the website, ticketing, support, and manages the chat room.

More people would be great, but unlike a live conference where you simply must have someone checking people in, front of the house, back of the house, vendors, and so on. It's just a lot less to manage.

Tracks and Days

Laracon Online has only ever been a one day, single-track event.

I don't think there's anything that precludes a multi-track event. I do think it's going to greatly complicate messaging to your attendees which is one of the harder aspects of an online conference in general.

Unlike a live conference, you can't just hang a sign and call it a day. You'll need links to the different streams; people may have to switch streams and have trouble when doing that. It means you'll definitely need 2 MCs and maybe more staff in general.

If it's your first online conference, I strongly suggest making it single track. In-person conferences often try to compensate for their high price with more everything. There's no reason to fall into that trap with an online conference. Edit the conference down to its core reason for being.

Laracon Online has also always been a single day event. I don't have a really strong recommendation on this. If you were considering going multi-track, I'd undoubtedly go multi-day instead to keep the management a bit easier if you're a small team.

Live or Recorded?

We've always run the conference as a live event. I'll introduce speakers, be available during the talk if there's a tech issue, and at the end ask them some questions from the audience.

Doing it live adds an element of togetherness that I feel is critical in trying to replicate some of what makes in-person conferences special. Everyone is experiencing the event as a shared moment.

That said, there are certainly advantages to having the event be recorded. You don't need a backup plan or have much to worry about on the day of the event. Most or all of it is set.

If you'd like a more produced look, this is probably the only way to get it without extraordinary expense.

There's no right or wrong way on this choice, but you'll want to think about it very carefully.

Timezones and Pacing

If your event is worldwide, you'll have some tough choices to make about the timing of your event. In our case, we generally start the first talk at 10 am EST and the last talk ends at 6:45 pm EST.

This schedule has worked pretty well for us. The majority of our tickets are sold in North America and Europe. This timing allows us to start at a time not too early for the US West Coast and which ends in Europe late, but not unreasonably so (at least for Internet geeks).

You'll also want to give serious thought to your breaks. You will not find a break schedule that everyone likes!

What we do is two talks and then a 15-minute break. As we usually have eight speakers that ends up being three break periods.

In this setup, I'm the one who suffers most 😃 having to run around in the break time to eat and use the facilities, but it works out, and it keeps the event moving no matter what timezone you're in. Stopping for a lunch/dinner break would make it longer which isn't suitable for some timezones, and since mingling isn't as seamless as a live event (in most cases), it ends up being wasted time.

Speakers

I'm not going to talk to much about picking your speakers. If you already run a conference your typical methods will work here as well. Instead, let's focus on how to treat and prep them.

First off, don't get stingy with your speakers! Your speakers doing a fantastic job is far more critical in an online conference than an in-person one.

There's no big party, special guest, or fancy concert that's going to hide your bad or poorly prepared speakers!

Since the speakers are working from home, you may be tempted not pay them and just have the invitation to speak be payment enough. I would strongly encourage you not to think that way.

A great talk is a lot of work, and for most speakers, this will be even more than normal as they'll be unconformable with the context. They may also be speaking in front of many more people virtually than they have ever before. You want them motivated and well prepared.

Paying a reasonable speaker's fee creates a clear business relationship and expectation. You won't have any other costs for your speakers, no flights, no hotels, so treat them well. For reference, at Laracon Online we pay each speaker $2,000.

Preparation

You'll want to check in with speakers leading up to the event and see if they need any guidance. However, there are some important elements that are unique to an online conference that you should touch on.

No Audience

When giving an online talk, you'll have no audience feedback. You're just talking at the screen. This may be uncomfortable for some people, and they may want to do a dry run or perhaps test their talk with a local meetup group via Zoom/Skype to get used to it.

Big Fonts

They'll be broadcasting to all different size screens, with many people watching on phones so they'll want their resolution or at least their font sizes to be larger than they might expect. This is always a tricky thing to balance when giving a talk regarding code and becomes even more complicated when everyone has a different screen you're trying to accommodate.

Tech Checks

As the organizer, you should set up a 'webinar' with the same configuration as the live event for each speaker. Then pick a time to meet with each one in the week or two before the event. They can enter the event as they would on the real day, and you can practice making them a presenter and transitioning them in and out of the event.

This also serves to make sure their tech is working. That they have the most recent streaming client, their mic works, etc. As the organizer, it also gives you a sneak peak at their bandwidth to make sure there are no issues with that.

Marketing

I wanted to add marketing in here for completeness, but I don't have too much to add about it. I don't think there's too much different here than for a regular conference. However, we do have one thing we do that could be useful.

Our conference is generally around February. You can then buy access to the videos of the conference up through when the next years conference site launches.

As an aside, this creates a nice little mini revenue stream. Only a tiny fraction of the main event, but it usually pays for the next year's site design and other ancillary things.

At the launch of the next year's conference site in the fall, we make all the videos from the previous year available publicly on the website. This drives fresh traffic to the conference site and reminds previous attendees about the event.

It's also something we highlight to sponsors as higher tier ones get their ads in the videos in front of one of the talks and so that ad is first seen by thousands of attendees and then a few months later by thousands of more people who weren't attendees but now get to see it free.

Sponsors

The idea of sponsoring online conferences doesn't come that naturally to companies. They're very geared towards in-person conferences. You'll often notice that the forms they make you fill out ask for a location with no option for online, etc.

Still, we've had fairly good luck acquiring sponsors. You'll want to focus on companies that are already working closely with you or with your community as they're more willing to go along with your experiments.

We're generally offering the following for our sponsors:

  • Logo and short ad read in front of one of the talks. That ad read stays in the produced video version of the talk.
  • Thanks via logo during the conference opening/closing
  • Website link
  • Shout out on Twitter and newsletters that we operate
  • Inclusion in the Digital Swag (this is key, more below)

Streaming Technology

We use Zoom and we're really happy with it. The first year we were very surprised how many people want to watch on the go. Zoom has clients for all the major platforms, and they work well. We've had to deal with very little support considering how many people attend our conference.

On conference day, what I do is stay logged on and in the Zoom the entire time. I'm the host.

My video will be enabled and I'll intro the conference. Then when it's a speakers turn to go I'll find them in the attendee list and make them a panelist. They turn on their video and screen sharing. I then turn off my video and mute my mic. I'll then watch the talk as much as possible.

This way, I'm always available in case I need to jump in and talk to the speaker. This is very rare, but I want to be able to act quickly should their mic be bad or their font size is too small.

Note: Be careful about jumping in on the speaker. Since they aren't expecting any feedback, it takes them off guard and it'll usually take them a minute to compose themselves.

Zoom Tricks and Tips

Each service will be different, but if you use Zoom, here are a few helpful tricks.

Buying Zoom

Zoom's UI doesn't make this entirely clear. If you're going to use Zoom, what you need to do is buy the regular $14/month account. Then you add the Webinar option to it. When you buy the webinar option you can tell it to auto-cancel after a month, which you'll probably want to do, though do leave plenty of time for the speaker tech checks before the conference.

You'll also want to add the additional cloud recording space to your options. That way, you won't run out of space in your account. I let Zoom record the video in the cloud. You can do it locally, but I'd rather not have my machine doing any extra work during the event.

Special Note What size webinar plan to buy is a bit of art. Zoom has set plan sizes and blocks people out if your stream fills. You don't want to overbuy as the streaming can get expensive, but blocking out paying customers is really bad!

In practice, for us, we've never seen more than about 60% of ticket holders in the stream at one time. We're genuinely a worldwide conference though making the times inconvenient for some. You'll want to carefully consider this for where your audience is and how many you might expect at peak times or for the most anticipated talks.

Turn off hand raising

Since this isn't a corporate meeting, you don't want attendees “raising their hand”, which puts up an annoying icon. Constantly. Zoom has this on by default and you can't control it in any of the settings. All you can do is as soon as the conference starts you can go into the 'more' menu and disable the ability to raise hands.

Turn on the green screen mode

In the Zoom client preferences, you can select that you have a green screen. If you do (and you should) it's ability to filter out your background using a photo (or animated gif!) will be significantly improved.

You can load a bunch of background images up in the days before the event so they're there and switch between them throughout the day. I've only used it for fun so far, but it could be used to show sponsor ads behind the MC or perhaps the schedule.

Share computer sound

One of the things we like to do is on the 15-minute breaks I play royalty-free music (find my track list here). To do that, when you share your screen to show your break slide (more on that below) you need to check the box to “share computer sound”. This will feed the music you're playing directly to Zoom allowing it to be clear for the audience.

Note: If you use Soundcloud to setup your break playlist, be sure to purchase Soundcloud Go+ ahead of time so that it's ad free.

Protecting the stream

Some people will get elaborate with protecting the stream URL, but as we looked into it, creating a password per-ticket starts to get complicated. You'll end up in API land with Zoom (no fun!) or even worse CSV upload land (đŸ˜±). Those are support nightmares with much of the support being at the worst possible time, as the conference starts and hundreds of people who don't know their password or just purchased a ticket and weren't in the CSV.

Instead, we simply have a single password shared across all customers. So far, this has never been abused; we haven't seen the URL and password show up on Twitter, for example. This is one advantage of keeping your pricing low; it lowers the number of people interested in stealing your stream.

What we also do though, is add a note alongside the password to make clear that sharing this URL/password could be detrimental to the entire conference. So far, this has worked great! If you trust your community, I'd certainly recommend this as a starting point.

Ticketing

You can use a regular ticketing solution, but to keep costs down, I'd recommend using a solution that lets you use a Stripe and/or Paypal account directly. There are many solutions out there for this.

We ended up building our own little app for ticketing, but more importantly, the app provides one place for all attendees to login to. That way, they can login and in the ticket holder area we can place the link to the stream and it's password on the day of the event, the page with Digital Swag, and so on.

Your ticket holder page doesn't need to be anything fancy at all! A plain website page would really work just fine. If you want to get fancy you could do Wordpress with a membership plugin. Don't overthink it, you just want to be able to have a consistent place to always send people and where people will know to go.

All attendees know the login on the conference site is where:

  1. They buy tickets
  2. They get the link to the stream
  3. The Digital Swag is
  4. The videos are after the event

This saves on back and forth communication as well as day of event frustrations.

Free tickets

Don't forget that there's going to be a lot of people you give free tickets to. Sponsors who get tickets, other interested parties. You'll want to have a way to issue those.

Pricing considerations

I can't tell you how to price your conference, but I do believe you should shy away from traditional pricing. There's plenty of room for profit in an online conference due to the significantly reduced cost structures. The best thing to do is pass those savings along on a per-ticket basis and try to reach a wider audience.

For Laracon Online we have early bird pricing of $12/ticket, and after that, the price is $25/ticket.

Unlike a traditional conference there's very close to zero marginal cost to each additional ticket sold so you want to sell A LOT!

Attendees

Attendees will have a lot of questions, many won't have attended an online conference before. They may also have technical questions. You'll want to have some help desk software set up to manage your customer questions. The previous link is to my software if you end up in the market 😉

The key thing to reiterate though is to have a webpage with everything in one spot. Your emails, support replies, and reminders can then just send them to that page where everything is available for them in one place both before the event and on the day of.

Mingling

A critical part of in-person conferences is meeting other people. That's going to be a challenge in this case.

The first year we used Slack. This ended up being pure chaos. Even with dozens of channels, having 4,000 people all talking about one topic at the same time become impossible to follow or supervise.

If you have a smaller conference Slack is probably an OK choice though. It certainly does help add to the feeling of all being together.

What we've settled on is using a Discourse server, which if you're not familiar with it, is a modern forum solution. A forum provides a more thoughtful and manageable context for online discussion.

Attendees can create threads and have discussions. It's also where they can post questions under our 'speaker questions' topic, which I read during the talk and cherry-pick a few out of for the post-talk Q/A with the speaker.

In our case, for those who want the adrenalin rush of a chat room, the community has filled in the gaps with unofficial chat locations on Telegram, Discord, and Slack. We'll tweet these out when they popup so that attendees can find them, but we don't moderate those.

Viewing Parties

Viewing Parties are something that grew organically out of our community. People started asking if they could watch the show together? Duh, of course! What a fantastic idea.

Every Laracon Online there are 20+ viewing parties around the world, each with between a handful of people up through 80+.

We advertise the parties right on our homepage, where they're listed and we happily add them when we're told about them. We'll also push them out on Twitter to help spread the word. They're often formed around existing meetup groups or companies active in the community, so those would be great people to reach out to and try and kickstart a party.

A note on ticketing

We request that each person at the conference has a ticket, but it's not something we strictly enforce (or that we even could). Only ticket holders will have access to the videos; however, so that does help encourage party participants to still buy a ticket. Especially at the low price we charge.

Digital Swag

Part of going to a conference is coming home with a lot of useless crap 😃 Fuzzy pens, a notebook with a brand name on each page, etc.

We didn't want to lose this experience! However, we wondered if we could do better. What we came up with was Digital Swag. We ask all our sponsors to provide something of value which we list on the Digital Swag page.

This alone usually ends up being at least 10x the value of the ticket price. So even if a customer only uses one item that alone will pay for the price of their ticket.

Sponsors get demonstrable leads; attendees get fantastic value.

Beyond that, we like to have as much swag as possible. So we also ask our speakers if they have anything they'd like to contribute. Most usually have a course, book, or product they'll add into the Digital Swag.

Gathering ad and swag details

A few weeks before your event, you'll want to be gathering up your sponsor's ads and Digital Swag details. We use a simple form like this to collect all those details from sponsors and speakers in one spot.

Note: People will be accessing your conference webpage long into the future, don't forget to collect expiration dates for any offer codes.

The MC

Being the MC at an online event isn't too different than an in-person conference. I view it primarily as helping keep the attendees oriented as to what's going on, what's coming up, and managing conference business (sponsor reads).

One unique element of an online conference is that transitions will inherently be a little clunky. You have to find and kick out the last speaker, then find and promote the next speaker to a panelist. To the audience, it's just going to look like you're wandering around your screen so you want to keep them informed of what you're doing. It might be useful to practice those transitions if you think you might feel uncomfortable during them.

Use a green screen

Most people don't have anything that nice behind them in their office. If that's the case for you, I recommend getting a green screen. The entire setup will cost you less than $100, and Zoom has excellent support for green screens. You can set your background in the preferences and there's an option to let it know you have a green screen. That will allow it to do a much better job at cutting in the fake background around your ears and hair.

Your presentation

You'll want to have a Keynote or Powerpoint presentation that you can work off of as the MC. This is where you can have a welcome screen, a slide you use on breaks, and your sponsor ads.

Get good lighting

You'll need good lighting. I haven't gone too crazy with this, but I do have a light on me and general background lighting. I plan on doing more with this next year. For more on this I recommend Matt Stauffer's excellent article.

A second computer

DO NOT FORGET THIS ON THE DAY OF THE EVENT.

You will need a second computer. During the event, you won't want to be messing with your main computer.

If you don't have a second computer an iPad with keyboard would probably work.

The second computer will be where you can keep an eye on everything else during the conference as the talk is being run through your host computer.

Videos

I'm not going to go too much into video production (see ours here). I'd recommend you set up Zoom to record your conference in the cloud. At the end of the conference Zoom will send you an email when the video is ready. Usually, a few hours later. It will likely be two files if you did an all-day event.

I just use Quicktime's split and trim features to break up the videos and then publish them via Vimeo. You can use Vimeo's features to restrict the domains the video will play on and other options.

You'll probably also want to provide downloads of the videos. If you don't, you'll get a lot of emails asking for it :)

While professional video production would be great, we've seen many conferences take this route and not get the videos out for weeks or more. With an in-person conference this is perhaps acceptable, but for an online conference you'll want to be much more conscious of the time to turn around the videos.

You'll have a huge number of attendees that could only attend part of the event due to timezones or work. The videos being available fast are something those people greatly appreciate. The last few years we've had the videos up the next day and people are extremely happy about it.

Subtitles

It's easier and more affordable than you think to provide subtitles on your videos. We use Rev.com, and it's been great. It's usually around $400 for the service.

You just upload your videos, and they have them transcribed into a standard format. You can then upload the text files with the subtitles into Vimeo or whatever hosting service you're using, and they take care of adding them in their player.

One note here is we don't wait for the subtitles to publish the videos. The videos go up as soon as they're ready. Subtitle creation takes a few days, so as those are completed, we just add them to the videos.

Backup Plans

Most in-person conferences have no backup plan. This is an area where an online conference has an edge.

There are a few areas you'll want to consider for your backup planning.

Assuming you're doing a “live” online conference one of the main things that can go wrong is something happening to the MC. Either they're sick and unable to MC or their internet is bad and they're unable to MC.

Either way, you'll want to have a plan for this. Make sure that someone has your login information for the streaming system and can take over as MC in an emergency.

The other primary scenario you might encounter is a speaker unable to attend.

We've never had that, but in our case, we've always planned to simply do a break at that point to stay on schedule and to provide video of the talk later if a speaker couldn't make it.

You could also consider having a group of people who could do a panel or an interview as a backup if you need to fill a spot quickly.

Having every speaker do a recorded dry run of their talk to have in the can is also an interesting alternative that also creates a bit of required speaker prep, which never hurts! We haven't done that ourselves, but it's something we're considering for future shows.

Unlike an in-person event, it would also be relatively trivial to simply move the date of the event if something goes wrong at the last minute. Sure, it will be a minor inconvenience for some, but nothing like having hundreds of attendees who've flown in for an event. It would only mean they'll watch the stream from work tomorrow instead of today.

Timeline

Here's a rough outline of what you should be doing when.

Months before

  • Decide on the format for your conference. Live/Recorded, the number of tracks and days.
  • Put out a request for speakers or invite speakers
  • Create your sponsor prospectus and start contacting potential sponsors
  • Identify your team
  • Build your website, pick your ticketing setup

Weeks before

  • Buy your streaming solution
  • Schedule tech checks with all speakers
  • Contact sponsors to get their ads and swag
  • Prep sponsor tweets and other requirements so they're ready to deploy on event day.
  • Setup your break time music playlist
  • Build your MC presentation

Day before

  • Restart your computers, make sure they're in top shape
  • Turn off your computer's screensaver and energy saver
  • Setup lights, camera, and green screen
  • Consider disabling messaging apps or using a network blocker like Tripmode.
  • Make sure your desktop is clean and organized. Everyone will wonder what the app dock icons are that you use, throw in a tricky one.
  • Get to bed on time

Morning of event

  • Get in early!
  • Setup your music so it's ready to go
  • Make sure you have someone watching who can tell you if you accidentally keep yourself muted or if there are other issues.
  • Send sponsor thank you tweets

Start the event

  • Join the meeting
  • Under 'more' turn off the ability of attendees to raise their hand
  • Put up your welcome screen and wait until start time. Make sure you're muted
  • At start time unmute and go!

After the event

  • Have a MaCallan 18 đŸ„ƒ
  • Pay your speakers
  • Process the videos
  • Submit videos to Rev.com for subtitling
  • Upload videos and email attendees that they're ready.
  • Upload subtitles as they're completed.
  • Make notes for things to change for next year

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This article is about greed. Greed in maximizing the rewards we get by the fact that as software founders, we pay for nearly everything with a credit card.

As Gordon Gekko once said:

The point is, ladies and gentlemen, that greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through, and captures the essence of the evolutionary spirit. Greed, in all of its forms, greed for life, for money, for love, for credit card reward points.

I've done a lot of research in this area and utilized points to fly my entire family to Europe for free, upgrade flights to first class, and buy widgets on Amazon (not a great use TBH).

How to use “Business” credit card rewards

Let's get one thing straight right now. You should not ever use your reward points on things you can expense in your business.

The reward points your business generates should strictly be for personal gain. All the banks allow you to transfer or merge your points with a personal account. I'm also fine with directly spending the points out of the business accounts. If you're an S-Corp or LLC there's no problem with doing so as they roll up to you in any case.

Using your reward points for items your business could otherwise expense doesn't make any sense. Take the write-off, keep the points.

Another side note is some of the cards have significantly better benefits than your personal cards are likely to have.

Discounted tickets, a 3x point bonus on a hotel stay, etc.

In a case where I can benefit by using the business card I will do so. You can then simply account for the cost as an owner draw from the business just as if you took cash out of it.

Tax consequences

I can hear you right now. Ian, this is great but you're going to get me thrown in jail!

Well the good news is that the IRS has almost no auditors anymore 😃.

OK OK, I have actual good news. The IRS has issued a ruling that points acquired on a business basis, but used personally have no tax consequences. Booyah!

In theory, if you used the points for business expenses, you are supposed to track the discounted amount and apply tax to that. However, as doing so is extremely hard to track this isn't done in practice. Regardless, it only makes the case stronger for using your business points for personal gain.

** What credit cards do I recommend? **

Let's get to the juicy bits. After much consideration, these are the cards I use to run my business. There are many others and The Points Guy is a good resource for exploring those. I think the ones below though will generally be the best bet for most software businesses.

FYI the links below include a referral link. If you choose to go with one of these using the link will kick me some points which would make my day!

Chase Ink Business Preferred

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Sign up here and I'll get a few bonus points (thanks!).

This is my go-to credit card. Chase points are worth roughly 2 cents per point and this card gives you 3x points per $1 spent on many transactions software companies make.

This card usually has an 80,000 point sign up bonus (worth $1,600) and only has a $95/year fee. Making this credit card a value monster.

3 of the 4 primary 3x categories are huge for us:

  • Travel expenses (airline tickets, hotels, etc)
  • Social media advertising (Facebook, Twitter, etc)
  • Internet, Cable, and Phone

The real key here is the “internet”, cable and phone. First off, we're all paying $150/month for our phones so pop that on there as well as your cable internet.

However, the “internet” category covers a lot of internet services we all use. Here's a sample of mine. Here are the transactions that were 3x last month for me. 20,500 points in total which is about $410 in points. Enough for a comfort class round trip ticket to Vegas baby đŸŽČ.

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Warning, these do change from time to time as they're based 100% on the transaction type coding the business uses. For example, one that hurt recently is our $4,000/month AWS bill stopped being a 3x bonus due to the recording of its transactions changing (more on how I adjusted for this below).

The other nice benefit of this card is that when you book travel through the Chase travel portal your points are worth 25% more. So that's a significant discount on hotel rooms.

Remember, only book personal travel(!) and account for it as an owner draw. Do book business travel on this card though to receive the 3x bonus points on your money.

American Express Blue Business Plus

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Sign up here and I'll get a few bonus points (thanks!).

American Express points are worth roughly 2 cents per point and this card gives you 2x points per $1 spent on your first $50,000 you spend each year. No annual fee.

What's great about this card is there are no special categories. You get 2x points on everything. So I'll put everything that doesn't register as 3x on Chase onto this card.

Since AWS is no longer 3x on Chase I've moved all that over to here which eats up pretty much the entire $50,000 limit 😞 but it's still 1x points beyond that.

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American Express points are great because they tend to be the most flexible with the most transfer partners of any reward program. They're the real bread and butter of a good rewards plan.

In addition, as these points pool with your other Amex cards the points earned here are even more valuable when paired with an Amex Business Platinum card due to the rewards that card offers such as the 35% points back program on certain airlines/airfares.

American Express Business Platinum

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Sign up here and I'll get a few bonus points (thanks!).

The granddaddy of rewards cards. The $595 annual fee and more unique reward structure make this card one you have to think about more carefully. However, if you value what it provides it can be worth having.

Most purchases are only 1x points with this card. So you won't want to use it for hosting costs, SaaS apps, or other such standard transactions.

Purchases over $5,000 are 1.5x points which is ok, but one of the other two cards above is likely better in most cases.

The Platinum card really shines with travel. First, most flights and hotels are 5x points as long as you book through the Amex travel portal. You'll want to shop around when you do this as I have sometimes seen it have worse pricing that alternative sites.

If you regularly fly one airline the Platinum card has a great bonus where if you pay for a flight with points you'll receive 35% of those points back, making it 35% cheaper to fly.

The 35% kickback also applies to business class or better flights on any airline. Sometimes that can bring your costs for such tickets down to less than a non-business class flight.

I used this with my family of 5 when flying home from Rome to New York with Norwegian who's not exactly business class business class qualifies.

Access to Fine Resorts & Hotels is another bonus. These are properties that Amex has worked out a special arrangement with. When booking with them through the Amex travel portal you'll receive 5x points plus some significant bonuses:

  • Free room upgrade (which are usually very nice at these sort of properties)
  • Breakfast for two
  • Early checkin, late checkout
  • Free wifi
  • and a bonus, which is usually a $100 credit to the spa or similar.

While this applies to elite expensive properties I've seen it applied to some less expensive hotels as well. It also always applies so if you catch a top tier hotel at an off-peak time you'll still get all the perks at a much lower rate.

There are also many other small rewards with the card that can really add up if you travel enough to take advantage of them:

  • Automatic Hilton Gold status and Marriott Gold Elite status allowing you to receive upgraded rooms, free internet, etc.
  • $200 in airline credits per year
  • Access to 1200 airport lounges including exclusive access to Centurion lounges.

So is it worth it? The Chase and Blue cards above are no brainers, 100% must have for any software founder. The Amex Business Platinum is much more case dependent. If you ever use any of the flight and hotel benefits it almost surely pays for itself even with the $595 annual fee. It also gives you access to better experiences which is valuable even if you fall short of covering the fee in savings.

A few parting tips

The dollar value of points stated above are generally based on utilizing points for travel. This is almost always the best use of points. Connecting it to your Amazon account and buying golf balls with it or redeeming them for gift cards is almost always losing 50% or more of the value.

Unless your business has a very large amount of spend each month you'll probably want to stagger adding these. Especially if you're interested the Platinum card as it has a pretty high initial spend to get the sign up bonus. You want the sign up bonus!

Finally, we've found that being more diligent about point acquisition and usage has been a real boon to our family. It's motivated us to take trips we otherwise would not have taken and allowed us to maximize the value of our business expenses.

The point is, ladies and gentlemen, that greed, for lack of a better word, is good!

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I normally keep it businessy around here, but with the holidays upon us I thought I’d share some of the products that have brought me joy this year.

If you’re stuck on what to get some people in your life (or on what to ask for yourself!) maybe this will help.

Duck money clip ($39)

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The best money clip there is. Holds everything securely and regains it’s shape after you’ve stuffed it full. I’ve used this for years and it’s never let me down. Ditch that fat wallet for the duck.

Buy it.

Canon 50mm 1.4 USM (~$300)

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Photo by Jonas Rask ~ review

I’m a Fuji X system photographer and those lenses are fantastic, but when I want to shoot something really contrasty and unique I reach for my Canon 50mm 1.4 USM. This was a lens built in the 50’s and 60’s.

They just don’t make glass like this anymore. It’s a real gem. I recommend taking a look at the review linked above by Jonas Rask if you want to see some great example shots.

As far as camera gear goes this is a real steal, usually available for around $300 in near mint condition on ebay.

One note, you’ll probably need a cheap plastic mount (available on Amazon) to connect this to a modern camera. It’s only a few dollars and works great.

Buy it.

Pure Ultrasonic Cool Mist Humidifier ($49)

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I’ve tried all the humidifiers. All of them. Pretty much all of them are horrible. Either they don’t work or they require a ton of maintenance.

If like me you’re mostly bothered by the humidity level at night when you’re sleeping the Pure is fantastic.

It’s design really only supports humidifying the zone of one persons sleep area. If you have a very small bedroom I suppose it may work for two people, but I find it’s best when it’s dumping that humidity right on your head :)

I never sleep without it.

Buy it.

Audible – The Lord of The Rings (~$15/month for Audible)

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Give the gift of Tolkien for the holidays. This is the VERY BEST version of The Lord of The Rings.

Better than the movies? Yes.

Better than reading the books? Yes!

The voice acting in this version (note the cover, this exact version) is simply stunning. If you’ve never heard this version you’re in for a treat.

Buy It.

Bean's Sweater Fleece Full-Zip Jacket

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This is my favorite fleece. I have it in multiple colors. It’s perfect for layering and works both dressed up a bit and down.

If you’re tall like me, it also comes in tall sizes.

Buy it.

Uniform Wares ($400-$1200)

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If you’re into really minimal watches Uniform Wares are great. Not too expensive (for a fancy-ish watch) and they really stand out.

They have nice designs for both guy and girl geeks.

Buy It.

Sieko Orange Monster (~$200 if you can find it)

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This is the one item on this list I don’t actually own.

It’s on here though because I really really want to :)

Very much the opposite of the Uniform Wares watch, Sieko dive watches are big chunky practical tools. There are many varieties of Sieko dive watches and many of them are really great. The Orange Monster is a bit unique and currently in demand.

They’re hard to find online outside of ebay and frankly I’m always a bit nervous about buying something like a watch off ebay.

However, if you’re not or you can find the Orange Monster locally grab it up.

Tao Te Ching ($9)

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America got you down?

Checkout a little eastern philosophy.

This is my favorite version of the Tao Te Ching. It’s a small pocketable version perfect for reading on the go or to keep on the nightstand.

I find it remarkably soothing.

Buy it.

Ciao.

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After my post yesterday about shady tactics in Bootstrapper circles people have been sending me other stuff they've seen that irks them.

In the other post I didn't call out specific people because I've seen these same tactics so many times that who it was that I saw most recently isn't even relevant.

This time though, I want to share one that's just so horrible I can't feel bad about sharing it. This is the kind of thing we must fight against. It's simply not acceptable and as I mentioned in the other article it may even be illegal.

Below is a video of what happens on the Quicksprout site when you provide them a URL to your website. In theory, it should analyze your site and tell you what's wrong with it. This isn't a new idea and while it's always a lead gen tool, other tools ACTUALLY DO ANALYZE YOUR SITE. See Website Grader by Hubspot for an example.

You know where this is going, but see for yourself. Oh, and stay until the end for some fake urgency as well.

These tactics hurt those of us trying to run real small businesses. They hurt the reputation hard earned by those of us grinding away on our businesses for the last decade. All of these people are smart enough to play the game straight and still win. They're better than this.

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Bootstrappers. I've been seeing a lot of shady tactics in our midst lately and I'm calling them out. These aren't good for you or your business long-term.

Some of these have already entered the zone of “conventional wisdom” but we need to push back on that. It really is possible to run a successful online business without stooping to these tactics.

Selling something that doesn't exist

I recently signed up for a course that was $500. It has a great landing page on a topic that I was searching for details on.

More than just a landing page, it was a list of the exact course elements with all calls to action clearly marking it as available right now. Buy this and have your grubby hands on it in 2 minutes.

I purchased. When I got access, there was only 2 videos that already were given out for free on the landing page. That's it. No other information, not even a notice directly presented that the course wasn't actually done yet.

After emailing the owner I found out that they were going to work on it over the next year.

That's great, but I have a problem today.

Being your lab rat isn't fun for the customer. It's not going to make the customer think highly of your product or service.

Yes, I know this is a popular technique to prove out the value of an idea.

But you know what, I think it fucking sucks.

Imagine for a second going into Wal-Mart. On your way down the cereal aisle you spot this great looking new box of Super Gummy Wheaties. You realize you're dying for some Super Gummy Wheaties and snap it up.

You wait in line, pay your $2.89 and drive home.

When you get home you get out a bowl. Get out the milk. Wash your favorite spoon.

Sit down and open the box.

Inside is.... Nothing. Fucking nothing. No plastic bag. No cereal loose in there. Nothing.

You know what you'd do? You'd freak the hell out. You'd be on Twitter cursing up the Wheaties people and Wal-Mart for running this scam of a marketing trial on you.

When you went back to Wal-Mart you'd demand a refund.

It wouldn't end there though. You'd tell everyone you know about it. “Can you believe there was NO FUCKING CEREAL IN THE BOX!!!”

And not just for a few weeks. Oh, you'd tell the story a lot in those first days, but this story would come up over and over.

Years from now, “Hey Jill, tell them about the time you got that cereal box at Wal-Mart and there was no fucking cereal in it”.

All this over a $2.89 box of cereal. If customers don't like it with cereal, if YOU wouldn't like it with cereal, how is this acceptable for a $500 product online? Why do we accept this because it's easy to trick people like this online?

I say it's not fucking acceptable. Don't do it. If you are doing it, stop doing it. Find some other way to validate your damn product. Stop tricking customers, hurting your brand, and in general being a bad internet citizen.

And I'll throw one more thing at you since some of you won't give a hoot about being a good internet citizen. That is that this practice is almost certainly ILLEGAL.

Yes, you. You reading this. YOU ARE PROBABLY BREAKING THE LAW IF YOU DO THIS.

Don't ask me, ask Jacoby and Meyers (you can trust them, we've all seen the ads on TV!).

False advertising is any published claim that is deceptive or untruthful. Misleading advertising is any published claim that gives a consumer an incorrect understanding of the product they are interested in purchasing or using. The false and misleading advertising by companies of any product may result in the consumer suffering a financial loss, or another form of damage to the consumer.

You see when you told me there would be cereal in this box and I purchased it thinking there was cereal in this box, I have the right to have purchased said cereal. Not just participate in some stupid fucking experiment.

This applies just as much to your SaaS app, your “content”, or your “productized services” as it does to anything else.

Alright? Alright.

Fake urgency

Oh I know you're not going to like me picking on this one. You're already mad from the last one! Well I'm killing all the sacred cows.

Now don't get me wrong. I love creating urgency. Urgency is a powerful sales technique. But your fake urgency is rude.

Recently I signed up for a SaaS app and on the sign up page I was offered the chance to jump the queue by sharing a link about the app. That's cool, I didn't share it and moved on.

I then start getting emails about how the queue is super long, but share it and I'll jump right to the top. I still don't share.

Then, maybe 24 hours since sign up I get yet another email urging me to share. I don't.

A few hours after that I get an email saying “Thanks for sharing” and I can now get into the beta.

FUCK THAT.

I didn't share your app. I'm not going to use your stupid app. I don't want to share it and your email sequence has exposed you as a complete fraud who didn't even bother to build or buy the system to reward the people who actually shared and instead you just send everyone the thanks for sharing email a few days after sign up.

That sucks for the people who did share and actually received none of the extra value that they were promised. Nobody wants to be treated like that.

You're just using a trick you read about on the internet. Does it work sometimes? Sure. That doesn't mean it's right to do or that it has no consequences if/when it goes wrong.

Oh, and I suspect this is also illegal in some implementations under the false advertising laws discussed above.

Injecting your company into other companies twitter "conversations"

We run a job board over at LaraJobs. When someone posts a job we tweet out the details with some hash tags of the tech used in this job.

Recently, a job board in the Angular space started tweeting about the companies who posted on our board. Even including us in the tweets under some shady guise and making it confusing for the customers who then thought they were associated with us.

Don't do this.

Don't freaking do this!

If you were at the Apple store and you were talking to one of the blue shirts how would you like it if a Samsung rep just jumped in front of you and started talking? Just out of nowhere, boom Samsung rep?

It'd be completely unacceptable. Not something Samsung or any company would ever do in person. We don't have to do this online either.

Must you sacrifice your own morals and common decency to run a successful online business? As someone who's avoided them for 12 years I can assure you the answer is NO.

"Follow up" emails

Hey, I've sent emails that probably have irked people. They haven't heard from me or my company in a while and bam, there's an email.

I get it. I really do. It's a very fine line here.

What's not a fine line?

Emails that you constantly send to your potential customers with subjects that reference fake emails or calls.

Emails that have fake reply headers in them from a previous fake conversation.

Anything that says “sorry I missed you” in the subject.

We all know these. We all hate these.

Yes, you might catch some people in this net but point me to the company that made their business on these techniques?

Do you personally get a lot of these from Basecamp or Fog Creek or Slack or Twitter or Apple or Amazon or Google or Microsoft or Typeform or Github or Moz or Rackspace or Linode or Dominoes or Tesla or Honda or Spotify or Stripe or Discourse or Pixel & Tonic or Ellis Lab or Facebook?

No you don't. This technique might help a sales person pad their quota. Maybe get you a few more bucks in your pocket. But it's NOT WORTH YOUR SOUL.

Oh yeah, it probably goes without saying at this point but these emails are probably also illegal. Not that anyone cares about illegal emails....

We're all focused on selling more.

Don't forget WHY you're doing that. Is it to take care of yourself, your family, and you're employees? Of course. But it all starts with the customer. Your business is done in service of your customer first. Without them you don't have a business and you can't help anyone.

Help your customers succeed. Don't let money blind you to why you started your business. Don't sacrifice your personal or business reputation for what is unlikely to amount to more than a few extra bucks on the bottom line.

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What is on your plate today?

My guess is that you are busy. You are running around with a To Do list one mile-long with things that need to get done, right now, no exceptions. There are meetings, and project status reports, and deliverables all requiring your immediate attention. If this sounds like you, you are in good company. Good company too focused on today, instead of future-proofing your business for tomorrow.

That was harsh. I’ll back up.

There is a quote attributed to Bill Gates that I really like. You might be familiar with it:

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

Think about that, and how it may apply to your business.

Modern software companies (heck, most modern businesses) are too focused on the right now and how an idea impacts today. The effect is that anything that may take more time to unfold (two years, five years, ten years, etc.) is seen as too risky or something the business simply can’t afford. We don’t even consider it; it’s just struck from the conversation. We make laundry lists of everything that has to get done today, tomorrow and next week, but beyond that, crickets.

I wonder if Bill is right that we underestimate what we can accomplish in a decade or if we’re too distracted with today to even think about it.

The trouble with this is obvious – how do you build a future-facing business when you’re rushing to achieve today’s inbox zero?

You can’t.

However, by flipping your thinking, weighing decisions on the value they’ll offer long-term, two big things immediately change.

You Prioritize Time Differently

Go back to that mile-long To Do list. It’s overwhelming, isn’t it? Take a step back and analyze the items on it. Ask yourself:

  • Is there a connection between what’s on the list and where you see your business 10 years out?
  • Is that side project you are working on adding long-term value, or is it a distraction?
  • Are you moving your product to where the market it is today, or where it will be in a decade?
  • Are you busy, or are you being productive?
These are hard questions because many of us won’t like the answers. Being busy fulfills our ego, the guilt and the silence of our day. But being busy isn’t how you’ll grow a business.

You grow your business by weighing every action and every decision against the value it will bring. Not today’s value, but long-term value. If it won’t add value in 10 years, it is not valuable today. It’s busywork.

You can never know, of course, if what you’re doing today will really payoff in 10 years (we’re still waiting for that time machine
) or if your visions for 10 years from now are even the right ones, but the thought exercise alone is revealing when you take it seriously.

You View ‘Big’ Projects Differently

Judging today’s actions by tomorrow’s metrics has the power to change your perspective, especially for larger projects. This is something that has been very important to us recently. There are some large scale projects that we have been putting off because they just seemed too big to take on. These are projects that will take at least one year to complete, maybe even two years.

Two years.

In software, that seems like a long time. It seems like forever, actually, especially for a small company.

But let’s turn the tables on that thought process. Instead of thinking about how long it will take to accomplish the task (the initial two years), think about the value you will create for the business for eight years after that by having done that work.

Two years of work in = Eight years of value out

That equation helps add important context to our decision-making, focusing on the benefit, not just the time investment.

Spending two years to achieve eight years of value is smart investment.

Spending two years and NOT achieving eight years of value is NOT a smart investment.

That’s easy to see and to understand, right? This is how we have begun to make business decisions at HelpSpot– weighing the investment against the value. Again, you won’t always be right, but just thinking about it has the power to really impact your business.

Try this out in practice today – take a look at your To Do list and really consider the tasks making up your day. Will accomplishing these things move your business forward and continue to provide value 10 years from now, or are they distractions keeping you from what you could be tomorrow? If they are distractions, consider which tasks you can weed out to make room for the work that really matters. You can achieve a lot in 10 years, but only if you start today.

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Money. The more the better, right?

Customers. The bigger the better
 right?

When you’re a bootstrapped start-up, you quickly realize that neither of those assumptions are correct. Of course you want more income. You’re trying to keep the lights on, after all. And of course you want customers who are going to be stable, loyal and paying enough to be worth your investment of time and resources.

But an interesting conversation begins here, as the dilemma of whether or not to sell to enterprise customers arises. Could a high-paying, prominent customer’s demands lead you make decisions you’d have otherwise avoided in order keep them happy? Maybe.

Should you have a hard and fast rule that you avoid enterprise customers? Some would say so, but I’d argue absolutely not. These customers can be good for your business, in moderation. It’s all in how you handle your sales process and your client relationships. It’s in how you decide to serve the enterprise customer, and who at the enterprise you serve.

The Argument Against the Enterprise Customer

Jason Fried made a great case for why a handful of high-paying customers can spell disaster on a small company in its early days. From “Don’t let anyone overpay you:”

We’d much rather have hundreds of thousands of companies paying us a small monthly payment than a few huge accounts covering that same amount. A diverse customer base helps insulate you; a few large accounts can leave you vulnerable to their whims.

He’s right on a number of points. True enterprise sales can be highly distracting to a team that is still trying to define its own products and place in the market.

It’s no small feat to land and keep that enterprise customer.

  • The networking alone can require fancy suits, steak dinners, travel and extensive negotiations.
  • Once the paperwork is signed, extensive software customizations, custom implementations, custom training, solution architecture and more may be required – all taking time and resources from the development you intended to focus on for your larger customer base.
  • Large companies—brand names you want to say you work with in your marketing and sales initiatives—can be tempting to bend over backwards for to keep happy, leading to extra client relations time spent managing the account.
And once you’ve spent all that time on the one or two big enterprise names you land, you risk finding yourself in the position of having these two companies dominate the majority of your revenue. What if one client decided to walk?

It’d be a bad day. Probably a horrible one that taxes your small group of employees tremendously.

And that’s why certain protections have to be made when you engage with such a powerful client.

Don’t Abandon the Enterprise

As a small bootstrapped company, you can sell to enterprises without these negatives, if you structure your mindset and your offering correctly.

Selling only to customers paying you $25, $50 or $75 per month can be extremely hard, especially as you’re building your business. You need an incredible volume of customers to be sustainable at those rates. Meanwhile, having a few higher revenue customers can give you more flexibility in these early growth stages.

So, how do you embrace the enterprise? Selectively! Find a few special cases that not only provide you with profit, but that also allow you to scale for them with limited hurdles and customizations. Find the enterprise cases whose needs and intentions best match where you’re already headed. By doing so, you can sell very profitable, large contracts without most of the extra work and expense required with typical enterprise customers.

You can work with the big customer, without losing sight of the big picture.

Truthfully, your enterprise work is best done if you start... small.

Define Your Target Enterprise Customer

“We want the enterprise customer.”

Correction. We want the customer at the enterprise.

When we say enterprise, we’re not talking about solutions that’ll cover the entire Fortune 500 company. Only in the rarest of cases will you be able to make those sales (and if you do, enjoy spending all of your attention on Company X’s Version Of Your Product, instead of developing Your Product).

We’re too small to manage the processes required to sell and manage the bit of software used by every employee in a 40,000-person company. In our earliest stages, with our 2, 4 or 8 employees, most of us are too small to provide such a substantial bit of software that’s at the core of that company’s functions, on top of all of our other customers’ needs.

But we can get our fill of the enterprise, by nibbling at the edges.

How?

At HelpSpot, we look at departments, groups or slices of functionality at large companies, and identify which sectors we can immediately impact.

We ask: What tasks can we assist with through smarter software solutions? How can we partner with them to make key processes within their part of the enterprise more efficient?

We then connect with a key decision maker within that space of the enterprise, and introduce our solution to them.

It’s not always an easy sell. That enterprise employee may not have immediate clearance to purchase your services, but you will have a much easier time implementing your service for 10 people, or even 40 people, than the 40,000 company-wide.

And that’s okay, because providing your service to 10 People Who Work At An Enterprise does not have to be dramatically different than providing your service to 10 People Working At Your Small Business Customer.”

Make Your Mark On The Enterprise

At HelpSpot, we’ve provided tickets management for individual retail location managers across a 500+ location customer, one by one. We’ve also worked with IT groups within enterprises, and directly supported internal maintenance groups. We’ve provided ecommerce support for a large record label where e-commerce was an important yet secondary revenue stream.

We work with groups within enterprise companies, without incurring the massive headaches and demands that come with the typical enterprise contracts. We provide value to them, while they also provide tremendous benefits to us.

By dipping our toes in the enterprise water, we learn quite a bit about our processes and our products. We learn whether we can sink or swim serving the big brands. We get stronger. We begin building better products, buoyed by the financial support of customers who can afford our top offerings. All the while, they offer us a bit of a flotation device to get us through our worst growing pains.

Enterprise customers don’t have to be the heroes or the enemies of bootstrapped companies. They can simply be customers that help drive your business forward, right along with all of the other companies you strive to work with day after day.

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People go to conferences with the wrong mindset. They feel as though they have to get a lot of information out of it or make a lot of contacts. They need to justify the expense with volume.

For me, I only ever have one goal and that is to get one actionable item from the trip. It could be an idea or a connection. Either way, if I leave with one solid next step it easily pays for the cost of the conference.

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This is simply a beautiful interview. If you're in business there's no way you can't love the clarity of his vision. The elegance of his presentation.

Grab a cup of coffee and enjoy.

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You spend a lot of time as a bootstrapped software founder on a knife-edge.

How can I afford to start a business? Will the business succeed or fail? Will anyone buy my product?

Once you overcome these questions you need to start thinking about hiring. There are a lot of great reasons to start hiring early in the success of your software business. I waited way to long with UserScape to start hiring.

This post isn't about all those reasons you've already heard about. To feed the growth, to get to the next level, to move faster, to build up sales, etc. This one is much more practical.

As you cross that line from barely making it to relatively profitable you're in an extremely dangerous position. As a solo founder or even potentially in a partnership what happens if you get sick? If you have a serious family situation? If for some reason you can't run the business for 6 months?

Not fun things to think about, but as you've probably left a good job and invested a lot of time and money to get this business going these are things you should think about. Having even just 1 great employee can make all the difference.

Even if they're not a programmer and no work gets done on the product. Someone to answer the phone, do support, help sales, and keep the lights on can make all the difference between returning to a going concern and a dead husk.

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