Why we raised a small round (and why you should think about doing it too)

Today we announced we’ve raised a $2 million dollar round of funding for AffinityLive. More than three years after our launch, this is the first institutional money we’ve taken; until now, we’ve built a crazy-ambitious product and worldwide client base through bootstrapping.

Over these three-and-a-bit years, we’ve grown the business to have millions in annual recurring revenue, a team of 40 amazing people across our two offices in San Francisco and Wollongong, Australia, and thousands of incredibly active and addicted users who trust AffinityLive to run pretty much their entire business every single day.

So, it might seem strange to folks who follow the startup scene that we’ve only raised $2 million in funding. Raises of $2 million are more commonly associated with startups who have an idea and some validation but no real product yet, much less revenue. So, what’s the deal with raising what is, comparatively, a small amount of money?

The fundamental reason is that we didn’t need to raise more to execute on our plan over the next two years – it is that simple. However, the fact that this even needs to be spelled out highlights what I’ve increasingly seen as an article of blind faith: the belief that raising as much money as you can whenever you can is a great thing.

While this advice is certainly true for some companies and entrepreneurs at some stages, I believe it isn’t right for most companies and entrepreneurs at most stages. Note that I’m focusing on the interests of the company and the entrepreneur here – not the interest of the investors (who are rationally self interested in perpetuating the “take all the money we’ll give you” model).

I’ll try to illustrate why the ‘raise as much as you can whenever you can’ model is often really bad advice with three analogies.

Raising money is like buying dinner


When you sit down to dinner, one of the first questions you ask yourself is “how hungry am I?”. If you’re only a little bit hungry, you should only buy an appetizer – even if the restaurant is offering you a deal on a 9-course degustation menu, getting a lot more food than you can eat is crazy. Some people convince themselves they’ll take it home for left-overs, but how often does it just get wasted in your fridge?

The lunacy of this approach becomes even more stark when you consider, in this analogy, you’re not buying the massive meal you don’t need with cash, or even with funds you’ve borrowed: you’re buying it with your equity! You can only sell equity once – so the idea of using the most expensive form of capital in the world to buy a meal you can’t eat without making yourself sick is super crazy!!!

The counter to this argument you’ll often hear (and always from investors, whose job it is to sell you money) is “fill your canteen when you’re at the waterhole.” This can be great advice for startups who face really uncertain or competitive markets (the amount you have to spend on marketing to win can double or triple overnight if your main competitor chooses to try to outspend you) or for businesses that aren’t yet generating revenue (no matter how you cut it, more money buys more time, and things always take longer than you think).

So, the key is to first of all honestly ask yourself how much you need to execute on your plan, ie, ask how hungry you are. Then you should resist the temptation to order up big just because you can.

Spending money is like getting fat


As anyone who’s tried to lose weight will tell you, it is much much easier to put it on than take it off! The same is true for companies – once you’ve increased your spending, it is very difficult to reduce it. While increasing the rate of spending (more people, bigger offices, more servers) is natural and healthy as the business grows, the risk for companies that raise big buckets of cash is that they don’t just get taller – they also get fatter.

A few weeks ago, I had a chat with a very successful founder who’d achieved a great exit. It turns out for most of their growth he’s been a bootstrapper; after a few years of hard slog, the company that was spinning off cash, growing strongly, and because of their gritty history, was run in a very disciplined fashion.

Eventually, after numerous approaches from investors imploring them to take money, they decided to raise a $10 million round. He regards this as one of the biggest mistakes he ever made. “Within 12 months, we’d blown over $4 million of it and had nothing to show for the money we spent.” They blew $300K alone on “executive recruiters” for four senior roles, only to have each hire turn out to be a dud. Even worse the culture had changed from one of discipline and taking on the world to one of comfort and entitlement. My friend explained how sad it was to realize that they’d lost the tight, high-performing culture they had, and how re-imposing that discipline was really really hard for everyone. He knows they only lost their way – and millions of dollars – because they had a bundle of money burning a hole in their pockets that they “let themselves go”.

Raising big rounds is like stunt driving


In an environment where entrepreneurs are expected to raise more money than they need, the natural consequence is higher valuations – which you would think is a great thing for the founders, right? A big valuation at exit is obviously awesome, but outsized valuations on the way through can be a disaster.

As illustrated brilliantly in HBO’s Silicon Valley a few months ago (Season 2, Episode 1), raising a lot of money at a big valuation can end in disaster – when you go to raise a lot more money later (which you’ll probably need to do because you got fat), you’re going to need to execute perfectly to earn the next big valuation (and so on in a repeating process through to exit).

The entrepreneur who’s raised too much at too high a valuation becomes the stunt driver, with the company the stunt car. Dramatic and death-defying, the stunt driver risks it all to justify the valuation the didn’t deserve last time, and to reach for the next valuation and big raise before they run out of money. This challenge of skill and luck is entertaining to audiences (the media, the public, envious entrepreneurs) and hopefully gets a great return for the promoters (investors).

But, if the stunt driver crashes out or hits a wall – perhaps there was a bump in the road they didn’t see, or there was a change in the conditions (capital markets) that caused them to crash – the audience sigh and go home, and the promoters call their insurance company or look to one of their 20 other stunt drivers to perform tomorrow. However, the stunt driver goes to hospital and the car is written off and sent to scrap, and while the audience and promoters are back to it the next day at the fairground, the stunt driver isn’t making it back for a while, if at all.


The main conclusion is to make sure, as an entrepreneur, you focus on doing the right thing for the company. Don’t optimize to get a big splash in the tech press (they don’t have a lot to compare private companies with, so funds raised has become the go-to). Don’t optimize for the biggest paper valuation you can get (because the valuation top end will be for preferred stock holders who get their money back first). Don’t optimize for the fanciest brands or the most Hackernews cred. Because the truth is that all of those things are the fleeting sugar-hits of entrepreneurship – you should be optimizing for the success of your company, and that means raising what you need (with some buffer for uncertainty) and not more just because you can.

Inside Sales Idiot Nominee – April 2015

While the email campaigns are still as constant as ever, it has been a couple of months since I noticed a true face-palm email campaign.

Thankfully, the idiots at Varazo sent us a gold medal Inside Sales Idiot email this morning. Feast your eyes on this beauty!

Aside from the comical references to a Virtual GoToMeeting invitation and reference to the fact we can send email to them “24 hours, 7 days, 365 days, including holidays”, they also dove straight into their pitch with bullet points on a grey background and no attempt whatsoever to communicate value to the recipient. Idiots.

Inside Sales Idiot April 2015

A Few SF Tips for New Arrivals

This post was originally an email written to the StartMate 2015 companies soon to be arriving in San Francisco to pitch investors and raise their seed rounds. Hopefully this information will remain useful for other folks following in their footsteps and coming to this great but confusing city as wide-eyed entrepreneurs for the first time.


So you’ll be making your way to SF soon – congratulations. If previous years have been anything to go by, you’re about to take the rate of learning and iteration up an order of magnitude – and I’m not kidding. So get some sleep on the flight (ask your doctor for Murelax) and don’t drink too much free AirNZ wine.

Here’s a few unsolicited tips that aren’t about fundraising and convertible notes and getting in TechCrunch. Those things are important too, but Hackernews has heaps of coverage and we’ll be able to give you specific advice. This is more general human stuff to help you acclimatize for your stay (which can be very open ended – there are many StartMate companies that never really left); I’m sure other mentors can chime in with more.

  1. Never call this city “San Fran” or “Frisco”. You’ll be politely chastised at best. It is SF (pronounced “ess-eff”) or “San Francisco”.
  2. The local Basketball team are the Golden State Warriors. They’ve just had a record season of regular play (4 more games to go in next 9 days of regular season) so they’re looking good for a deep playoff run; the city will lose its mind. The Giants are the baseball team who won the World Series last year and they’re just starting their season at the moment. The 49ers have Jarred Hayne from the NRL this year, but won’t start until September so nothing to see or learn about there.
  3. The city is a grid (like Melbourne or NYC) cause it burned to the ground after an earthquake in 1906 so they got to re-do it right in most places. Don’t think about earthquakes though when you’re here – they’re out of your control so just make sure you sleep with some clothes on. The grid is weird though cause there are massive mountains here they built the city on & the blocks do their best to follow the shape of the land and shoreline while staying straight. The equivalent of George St Sydney is Market St San Francisco. To the north of Market St the city blocks are orthogonal (still perpendicular blocks, but angled at 60/30 degrees as they intersect Market St). The south of Market St is a regular grid parallel to Market, starting with 1st St in the east and continuing on. It stops being quite so regular after 10th St; the grid follows Mission St (which until this point is parallel to Market St) as it bends away from Market to the South. This is what allows a low street number like 3rd to end up running perpendicular to the “bent” streets of 16th further along Mission St. Sounds confusing, but ain’t so bad when you just remember that the point of reference for numbered streets is always Mission St – it is the backbone and the numbered streets are the ribs.
  4. This place is the homeless capital of America. There are like 20K homeless people here. Sydney has 346. Prepared to be confronted. Many have mental illnesses and SF is a draw across the US because it has (comparatively) great social services and the climate and the police are both mild enough that if you’re homeless you won’t die here. As a general rule, the homeless are also non-threatening (either because they’re genuinely lovely people chewed up and spat out by America and its wars, or because they know the generousity of this city of 800K keeps them fed – more money is spent by City Hall on homeless services than road maintenance). As a 6 foot man I’m never worried about them, but I know dudes 6 inches shorter who cop abuse and I wouldn’t be a woman walking around in SOMA or the Tenderloin after dark alone.
  5. SOMA, or “South of Market (St)”, the home of startups in the city, is also the home of the homeless. It is gritty and grimy, a place of recently converted factories, car workshops and sex on premise venues for that special kind of man. If you see poop on the streets of SOMA, you can be 90% sure it is human, not animal. None of that is a joke.
  6. Uber and Lyft have taken over the place. Only chumps catch cabs.
  7. T-Mobile has the best pre-paid GSM mobile phone deals. There’s a store near the cable-care at Powell and Market. The people there are genuinely lovely. Go and see them and tell them you’re looking for that $50 prepaid plan for your own phone and they’ll hook you up.
  8. While chumps catch cabs, good startup rain men and rain women work out public transit – it is plentiful, cheap and frequent. It is also a bit byzantine.
    1. Bart is used for getting from the Airport to the City or the “East Bay” (the collective name for Oakland and Berkeley and a bunch of other suburbs/cities), and trips are priced by distance with tickets purchased before you board via either a stored value RFID-card called a Clipper or through a single use paper white ticket with black lines and a blue arrow.
    2. MUNI (which stands for Municipal Railway) has no trains – it is bus and some light rail. It runs all over the City of SF, but not (far) outside it. Trips are all a flat rate of $2.25 and you can change bus/light-rail as much as you like within a 2 hour window for the same $2.25 fee. This can also be funded through the pre-paid Clipper card which is a good idea because bus drivers can’t give you change (all money is locked away; see homeless above and crackheads below for the legit reason). Buses are slow but can get you anywhere. If there’s a few of you though you’re better off taking a Lyft (taxi driven by regular lovely people), Lyft Line (like Lyft, but you might have to share, but the price is fixed, max 2 people per request), an Uber (UberX is the regular person driven one) or UberPool (a ripoff of Lyft Line). However, there’s certain startup/hacker cred that goes with knowing the way to get from StartupHouse to the Golden Gate Bridge is via the 6 to the 47 and then along Van Ness to Chestnut where the 30 will talk you a few blocks to the 28. Don’t make a rookie mistake and use Golden Gate Transit or Samtrans.
  9. The city is a young person’s paradise – there’s literally something for everyone, and many things for people you didn’t think exist. A few tips on neighborhoods if you’re venturing out:
    1. SOMA. Startup central by day; Blue Bottle, Sightglass, Epicenter, The Grove and the Creamery are all coffee shops teeming with smart people on laptops or doing pitches. The energy is nuts and you’ll learn a lot by listening to the table next to you. By night, it is a place for dealers of narcotics, clubbers and the destitute.
    2. Union Square/Financial District. Active by day with shopping and office-working folks (they have a special punitive tax for companies in the financial district, and people are dressed very well), but by night no-one is here save the tourists still waiting for a cable car or a seat the the Cheesecake Factory. Don’t do it.
    3. Tenderloin is like Redfern but 10x worse. Crack heads everywhere. Like walking through a zombie apocolypse film. Don’t go there at night. Is north of Market between 5th and 10th St, and very close to Union Square – tourists often take a single wrong turn out of their 5 star hotel and end up in Skid Row. Don’t do it.
    4. The Mission. Great spot running the length of Mission St from 13th to 26th St (roughly) and 3-4 blocks either side. Popular with artists. Formerly the badlands of the city with big gang problems in the 90s, it is now either the first or second most bohemian part of the city. Still pretty gritty around the Bart stations of 16th and 24th streets, the place has a lot of dive bars (small bars, low standard, cheap booze, no pretentiousness) and great restaurants. It has the second worst guy to girl ratio in the city after the Castro however.
    5. The Castro. Slightly north-west of the the Mission, the Castro is an awesome place of friendly people and rainbows for dudes. The rainbow ladies are more centered around Bernal Heights, which is where you end up if you keep going down Mission to like 30th St equivalent. The bars in the Castro get very loose as you’d expect for a place that is basically the Sydney Mardi Gras every Saturday night. Welcoming and fun for everyone.
    6. The Haight. There’s actually two parts; Lower Haight (centered around Haight and Fillmore) and Upper Haight (Haight and Ashbury), which vies with the Mission to be #1 bohemian. The first part is a kinda gritty neighborhood with some good sports bars. The latter is the home of the 60’s flower-power free love movement and you’ll still get stoned walking down the street on a Tuesday morning if you breathe in deeply, however, it is so grimy and commercialized with Bob Marley t-shirt stores you’ll prob be a bit sad if you head to Haight Ashbury listening to the Mamas and the Papas on your headphones and seeing the reality of flower power free love’s 40 year hangover. Some decent cocktail bars like Alembic up there and a brewpub that makes their own beer called Magnolia.
    7. Polk St/Russian Hill/Nobb Hill, which are due north from Market and 9th St. Increasingly nice places to live, these places have a lot of great bars and competition. Nothing to see during the day. The #19 bus will get you along the length of Polk to the San Francisco Bay.
    8. Fisherman’s Wharf. Northern side of the city on the bay. Tourist trap. Avoid is except for going to Alcatraz, which is highly recommended. Get your tickets ahead of time from www.alcatrazcruises.com though cause it sells out well in advance.
    9. North Beach & Telegraph Hill. North of Market and 3rd st, not as far north as Fisherman’s Wharf, this place is like SF’s Leichhardt. Italian food, lots of bars with different things going on and not too pricey (except for the strippers on Broadway, which is like Sydney’s Kings Cross). Nothing to see in the day.
    10. Marina. Is on the northern side of the city right on the bay. Like SF’s Bondi – more girls than guys live here which is one of the only places in the city where that is true. Two streets, Chestnut and Union, run parallel and have prob a dozen or more bars each and a bunch of great restaurants. 99% chance you’ll end up at the Tipsy Pig on Chestnut St (between Piece and Scott) while you’re here. Has best access to Golden Gate Bridge and incredible waterfront parks (Marina Green and Crissy Field).
    11. Hayes Valley. Carved out of the space left behind by the 101 collapsing in the 1989 earthquake, this neighborhood still has a lot going on but is more for couples who are sick of the craziness of Polk/Marina and want somewhere nice and central (it is super close to all the transit running under/along Market St). A great outdoor beer garden and some innovation with shipping containers to overcome the moribund failure of town planning of which won’t let anything happen anywhere, ever – the containers aren’t “permanent” so they can be awesome without the city.
    12. Noe Valley, Cole Valley, Hayes Valley, Western Portal, The Richmond, The Sunset; these are all great neighborhoods but very residential and quite family focused so not somewhere you’ll prob find yourself unless you’re bringing out the family and looking for a 3/4 bedroom family home. One exception is around UCSF just beyond the Upper Haight – the restaurants and bars are clustered around 9th Avenue and Irving. Oh, yeah, the numbered “streets” are close to the Bay, the numbered “avenues” are closer to the ocean on the western side of the city.
  10. Silicon Valley“, which includes Menlo Park, Palo Alto, Mountain View and Sunnyvale is a pretty boring spot from a visit perspective – imagine North Ryde that runs for 50kms down a highway called the 101. Travel time from SF to Palo Alto varies from 40 mins to 140 mins depending on traffic. Public transport is almost non-existent. Transport options include CalTrain (runs between hourly and two hourly), getting a Zipcar account (pay by the hour car hire), hiring a car (Avis etc) or bumming a lift (easier than you’d think for things like the demo day down at 500 Startups if that happens again). A bunch of investors are down there – you’ll get a feel for your need to head down there pretty quickly (many VCs have moved operations to the city cause that’s where the cool companies are).
  11. On a weekend you should totally hire a bike from North Beach/Fisherman’s Wharf and ride west along the waterfront past the Marina and then up and over the Golden Gate Bridge to Sausalito. You can then catch a ferry back (Blue and Gold Lines, buy tickets on board for $12 or something) to Fisherman’s Wharf past Alcatraz on what has to be the world’s best antidote to the stress and fear of building a startup. I’m not kidding or getting zen about it – this ride in the clear crisp air of the north west Pacific over probably the world’s most beautiful bridge and then back across the Bay to a late afternoon/sunset cruise for less than A$20 is pretty damn amazing. Don’t worry about getting lost – the bike hire guys have maps for you on the bikes and you can follow the herd to an extent.
  12. Speaking of the north west Pacific, it is cold here most of the time. The wind hasn’t hit anything since it left the Bearings Sea off Alaska where they shoot the Deadliest Catch. Always have a jacket – a hot steamer of a day will have you shivering by 5pm most of the time, especially if the fog rolls in (which it does with depressing reliability between June and August, ruining our summer). If you don’t have a jacket you like already, don’t worry – everything is cheap in America. The Burlington coat factory (5th and Howard, right near Startup House) will have your jaw drop when you see the selection and prices.

What tips did I miss? Feel free to add your own in the comments.

Finally Breaking Up With Windows

I’ve been a user of Windows since the version 3.0, but this weekend I finally broke up with Windows. While there were plenty of times Windows had frustrated me in the past (Vista anyone?) the debacle that is Windows 8 was the final straw, and I’m pretty confident I’m never going back.

TL;DR: if you’re sick of the piece of shit that is Windows 8 (if I wanted to buy a tablet, I’d buy a damn tablet), and you don’t use MS Office (or can use LibreOffice or Google Docs instead), you should definitely move to Ubuntu. It is now ready, faster, better and easier to use than Windows (and probably has been for a while).

A Tale of Two OSs

For the first half of my time using computers (early 90’s to mid 2000’s), Windows was clearly the smart choice. While many friends in college in the late 1990’s were Mac die-hards, even they knew their decision was more a religious than an intelligent choice – they rejoiced in their cause of “resisting the borg” while all the time being frustrated at all the things they couldn’t get on a Mac.


For the second half of my time using computers, Mac has undergone a resurgence. While the latest stats show Mac with only 7% of market share for desktops, any visit to a tech conference will show non-Mac users in a minority. Now I find myself being the holdout on grounds of belief and principle – the thought of supporting the closed and restrictive practices of Apple has held me back from joining the legion of other tech professionals moving to Mac (for reference, Microsoft at their worst never tried to control the software you could load on a device you own and have paid for – and while the Mac retains freedom for now, the App store model of control and 30% cuts continues to push its way into desktops).

To be fair, Windows 7 was a pretty decent operating system. I see more rainbow spinning balls on my friend’s Macs than the lockups and blue screens of death than I ever saw on my Windows 7 laptop, but more importantly, in the last 5 years I’ve pretty much stopped caring about or seeing the operating system – I pretty much live in my browser and everything that matters lives in the cloud in one way or another.

Windows 8’s Larson-Green Oversteer into a Cliff

After completely blowing its head-start in mobile touchscreen technology (I remember buying a Windows Phone 2003 smartphone back in the early 2000’s) due to corporate infighting and bureaucracy (see Kurt Eichenwald’s brilliant story, “How Microsoft Lost Its Mojo: Steve Ballmer and Corporate America’s Most Spectacular Decline” in Vanity Fair), Steve Jobs finally had Microsoft spooked.

By 2012, with the runaway success of the iPhone over the last 5 years and the iPad gathering steam with more than 60 million sold that year, Microsoft made a fatal mistake with their design decisions on Windows 8: instead of improving on Windows 7 and introducing options to be more tablet-friendly, they yanked too hard on the wheel and crashed the Windows franchise into the cliff.


To prove to the market Microsoft was serious about the threat posed by tablets – which have since proven themselves to be more entertainment systems and toys than places to do work – they decided to destroy the user experience of desktop Windows (used by 1.3 billion people around the world with more than 90% market share still) to chase the shadow of the tablet market (of which Windows makes up only 6% of a market, and after rapid initial growth the whole market is now slowing significantly).


The irony is incredible; a year after his passing, the legacy (or ghost) of Steve Jobs had caused Microsoft to make one of the biggest blunders I’ve seen in corporate history: Windows 8.

While Julie Larson-Green wore the blame for the disastrous decision to replace the Windows start-menu, there were many more problems with Windows 8 – and all of them made me feel like I was being poked deliberately in the eye so the company could chase the tail-lights of a ghost.

Windows 8’s Many Sins

Windows 8 took so many steps backwards in terms of usability it is hard to believe the company could have made so many mistakes with just one release.

The “Start Menu”

The most obvious egregious example of Microsoft’s decision to deliebrately f*ck the customer was the Start Menu. Remember, an operating system exists to run other applications on top of it – and even when Windows 8.1 bought the start menu back, just starting an application was painful. Here’s what it was like Hipchat:

  1. Click on Start in the bottom left. Get dizzy when you lose every piece of screen real estate to the new start screen (remember, you want to start a chat app, not take over the whole screen).
  2. Scroll down past the news and weather and shit you don’t want to see when you’re trying to start an application. This isn’t instant – you still have “live tiles” of shit to get past before you head down to the actual applications.
  3. Apps are ordered alphabetically. But actually, they’re not. Hipchat isn’t under “H”.
  4. Keep scrolling, this time right. Get past apps starting with Z, and find the folder starting with “H” for “Hipchat”. There’s your app – Hipchat.

If you’re trying to use Skype, prepared to get extra fucked. There’s two of them. Why? If I’m confused, God help the regular punter.

Duplicate Settings Screens with Different Features

Users of Windows since forever will be familiar with the “Control Panel” or settings screen. It still exists in Windows 8, but it is one of many screens to be “Duplicated” with a more tablet-friendly full screen display. There’s a second “PC Settings” section, with different features. Getting out of it when you’re done will wear out your ESC key.

It is bad enough when you have to find something that has moved in a new version, but it is even worse when it half moved and you need to learn two different placed just to make things easy for a non-existent customer base. Just finding help is a nightmare – and spare a thought for the poor technical writers at Microsoft who now have twice as many docs to keep up to date to cover the same help content (search for “Windows 8 change resolution” for some fun).

High-DPI and Compulsory Blur

While all of those frustrations could be offset (the awesome Launchy app meant I hardly ever had to use the Start Menu, and settings hopefully only have to be used occasionally), I was reminded every single day about the lunacy of Windows 8 when I looked at my second screen: it was always blurry.

Windows 8 introduced a compulsory feature related to how it renders apps on high-resolution screens. My second screen’s native resolution was 1920×1080 (HD), and under Windows 7 everything looked crisp and normal.

After plugging in my new Windows 8 laptop into the screen, I found all of the fonts fuzzy and blurry. Aside from being ugly, my poor eyes were constantly trying to focus – I felt the strain. This wasn’t just annoying – this was unhealthy. It turned out the “solution” was to right click on an app and disable high DPI scaling or some such shit – this is 2015, and it worked find a week earlier on Windows 7 on the same damn monitor – but this just made all of the fonts janky and jagged. So, blurry or jagged were my two choices, because after all, Microsoft were chasing Retina display and wanted to optimize for Angry Birds on a fucking tablet.

Escaping to Ubuntu

I remember first trying to switch to Linux as my desktop OS back in the late 1990’s with RedHat 6 (Cartman), and the reality was it always required more work to get running (and keep running) than it was worth given my schedule. I really just wanted an operating system to operate – run apps, don’t crash, support the hardware with drivers so I can use the machine I’ve bought – and didn’t have the spare time after starting my first business in early 2000 to mess around with recompiling my own kernels and messing around with driver mods.

When Windows XP was released in late 2001, my flirting with Linux as a desktop OS ended; life got busier and the idea of going back to my hobbyist days of messing around with Linux as a desktop replacement had little practical appeal, especially since Windows XP was actually pretty good.

I avoided the Vista upgrade, and was happy to move to Windows 7 when I needed to upgrade my machine, but the forced upgrade to Windows 8 was a nightmare. After putting up with Windows 8 for over 3 months of continual frustration (especially for my poor eyes), I decided enough was enough – I was either going to move to Ubuntu or “upgrade” to the earlier Windows 7 (which wasn’t an option when I bought the laptop – thanks Samsung).

The result was nothing short of incredible. Within 30 minutes of inserting my USB drive in my laptop (with the live installation of Ubuntu loaded on it – super easy with UNetBootin), I was up and running with a fully loaded Ubuntu 14.10. It detected all of my hardware out of the box, and aside from a few shortcomings with missing function key toggles I didn’t ever use in Windows anyway, I’ve got a perfectly working laptop.

Free At Last, and So Much Faster

The feeling of being free from Windows is hard to explain.

Firstly, as a software developer who still codes regularly, relying on Windows was always a source of some shame, and increasingly a cause of frustration. While the irony of being a software developer on a Mac and thus supporting Apple’s policies of restricting who can use and run your creative output is something many others seem to be blind to, the reality is that OSX’s underlying BSD architecture is much more developer friendly. As a result, being a minority (software developer running Windows) meant that more and more tools (especially around Git) and tutorials were targeted to Mac users specifically; also an irony given the way Mac was an unsupported outsider platform for decades. Being on Linux has opened up the most developer-friendly tools I could ask for – and I’m already loving transitioning to them.

Secondly, as a performance user, I really appreciate things being fast. My currently laptop (Samsung ATIV Book 9 with an i7 processor, 8GB of RAM, SSD for storage) is a pretty powerful piece of kit for the price ($1400), but I often found myself waiting and frustrated with Windows 8.1. With this new Ubuntu setup, my laptop feels twice as fast. I don’t know if it is the lack of bloatware, the lower amount of OS overhead or something else, but my laptop is so much faster than it was this time last week.

Thirdly, as someone who’s bet everything on the cloud and browser-based interfaces, the ability to completely change operating systems on a Saturday afternoon and spend a weekday at the office not missing a single thing is pretty incredible. While I know that Google Chrome was going to come across fine and be the gateway into almost everything I need/use, I was pleasantly surprised to find Hipchat’s desktop app working well as a native Linux app, and most surprisingly of all, Skype for Linux being significantly better than its Windows cousin.

But the fourth and most important reason personally was that by continuing to use Windows 8, an operating system designed from the outset to poke the 1.3B+ desktop Windows users in the eye to justify Microsoft’s delusions and need to chase Apple’s tablet-tail-lights, I was giving them permission for all their bad deeds. As the dominant desktop OS vendor, they could continue to f*ck the customer and I was someone who put up with it – inertia was too hard to change. If staying with someone who beats you up gives them tacit permission to keep beating you, I wasn’t prepared to support it anymore. And I’m looking forward to helping my friends and colleagues escape too.


In summary, unless you have to use specific features that are only available in Adobe, Word or Excel or some other productivity tool, I can’t see a reason why you’d stick with Windows 8. While Microsoft are promising candy like Cortana (talk to your computer like Siri/Startrek – should be all sorts of fun in an office) with Windows 10 in 6 months or so, given what Microsoft have done with prioritizing a failed mobile strategy over the interests of their desktop users (and it is failed and done – Android is the new Microsoft with the vast majority of market share, and Apple is the new, um, Apple), I recommend upgrading to Ubuntu today – Linux is ready for you, and you won’t regret switching.

Inside Sales Idiot Nominee – Feb 2015: Albany Ford Subaru & Flagged No Response

This one sold itself as an ISI nominee from the subject – “Albany Ford Subaru – Flagged No Response“.


As much as I love getting an email with subject of the sender prominently displayed (hint: it is better to write a subject that your audience cares about), the inclusion of “Flagged No Response” as part of the subject was a unique touch of incompetence on the part of the folks who set up their Marketing Automation on Motosnap.

Also impressive was the inclusion of the big banner image – in a world where people are increasingly reading emails on their mobile devices, a big wide image like that with that amazing logo and picture of their building (?) is also a big example of what not to do.

Cutting your Comcast Bill in Half – Part 1, Internet


Comcast’s business model is simple – sell to new customers on a good deal and then rely on their laziness and ignorance to increase average revenue per account to thousands of dollars a year. Over the last month I’ve upgraded the internet at my house, my office and my girlfriends house and saved up to 50% while getting up to 6x faster speeds.

In this blog post I’m going to show you how to do the same.

Loyal Customers Get Screwed

The first thing – and this is the most important thing – to understand is that loyalty is actually punished by companies like Comcast. When you’re an existing customer, a whole slew of plans and options just flat out aren’t available to you – as the South Park creators so successfully showed, when you’re an existing customer, you’re completely taken for granted (or, “their bitch”, thanks South Park).

The good news is, though, that you can overcome a lot of these problems just by being disloyal.

Saving on Internet

Before starting this process a month ago, the three specific monthly bills with Comcast were around $100 including taxes.

Initially, I followed the great advice of people like GE Miller and went through the “account retention” process – where you say you’re going to cancel your account and get immediately escalated to the Account Retention team. These are the people at the carrier who are rewarded and compensated for keeping subscribers, and who have a lot of latitude in what they are able to “include” or discount to keep you as a customer.

The rewards and bonuses must be pretty good, because some of them get pretty crazy.

While this is solid advice, there are still limits to what these people can and will do, and often their lowest price and best upgrade offer is still a much worse deal than you can get if you’re not a customer at all.

The solution, it turns out, is actually pretty simple. You become not a customer. Here’s the four-step process (with a bonus Step 5 to save another $500 a year).

Step 1: Choose a Plan

Providers are always running specials and deals to get new customers on board. I’m not sure what their Customer Acquisition Cost is (CAC) but given the number of advertisements I see it has to be in the realm of $500-$1000. For DirectTV, Selling, General & Administative costs make up more than 50% of its gross profit a few years ago – this is a lot of money.

This also makes business sense; they know through cohort analysis that if they can tempt you in with a good deal they’ll jack up the price and your laziness will keep you where you are.

Since I’m in America, the land of the free market and competition, there is almost no competition in broadband internet access. Being in San Francisco, that means I’m limited to looking at options with Comcast. At the time of writing, they were offering a 105Mbs internet plan for $44.95/month; the options change all the time though, so check out http://www.comcast.com/xfinity-internet-offers and decide on which plan suits you best.

When you look at the terms and conditions of the offer, you’ll note that one of the first conditions is that it is “available for new residential customers only”. That’s cool – you’re about to become a new customer, with some temporary help from a buddy.

Step 2: Enlist a buddy for an hour

Now you know what plan you want, it is time to start the process of becoming a new customer by getting some help from a buddy – it should only take an hour of their time, and you can actually return the favor for them if they want to do it at the same time!

The key is that your buddy is going to be signing up to the new internet plan at your house. They don’t need to live there – there’s no need for proof that they have anything at all to do with your address; all they need is some photo ID and a social security number.

To make it happen, you and your buddy simply show up at your local service center (Comcast ones listed here), and tell them that you’d like to cancel your service. Your buddy, standing next to you, would like to sign up for the “available for new residential customers only” plan you selected in Step 1 above.

You’ll want to bring your cable equipment with you, but you can hold onto it for a couple of weeks if you like (since you’re going to be coming back to do the same process in reverse in Step 3).

There is normally an account setup cost of $30, but if you ask them for a discount they’ll drop it down to $12 without a fight at all.

If you need a modem (and you should really buy your own – see further down this post) they’ll give you one on the spot. You’ll then be able to go home and plug it in (swapping out the one you already have) and once you go through a quick setup process (their phone number, 1-855-OK-BEGIN, works pretty well – just don’t do it on speaker phone because if the computer mishears you you’ll go into a never ending loop) and you’ll be online with your new faster cheaper plan in no time at all.

Step 3: (ab)Use The 30-Day Money Back Guarantee

Now, perhaps your buddy is a housemate or a significant other – if they’re happy to be the one with their name on the bill for the next 12 months then you can probably skip this step. However if they’re genuinely just a buddy doing you a favor who doesn’t want to run the risk that you won’t pay your cable bill and their credit report will be on the hook (or that you’re going to do illegal things online and get them in trouble as the legal account holder), you’ll want to do the process involved in Step 2 in reverse.

The good news is that Comcast has a 30-day money back guarantee, so you can head in after a couple of weeks and have your buddy cancel the service you set up in Step 2. They bring the cable box you got in Step 2 in and they’re done in about 20 minutes.

You, standing next to them, decide you want to become a new customer on the same plan. You sign up for the new plan/service at your own address, and you’re back in business, possibly for half the price.

Step 4: Set a reminder for next year

Most of the plans I’ve seen revert to their “normal” price after 12 months. So, you’ll want to set a reminder to go through this process again in a year.

Step 5: Buy your own cable modem

Comcast are currently charging you $10 per month to rent a cable modem (or wireless router). This comes to $120 a year, or almost $500 for the normal life of a piece of technology like this.

The good news is that you can buy your own from Amazon for around $60 if you don’t need wireless, or $100 if you do, which means you’ll be ahead in financial terms in as little as 6 months.


Now, some of you reading this will be thinking “hey, my time is valuable – is this really worthwhile?” You’d be right to think this way, but let’s look at specific savings and see how wrong you probably are.

Comcast Business to Xfinity Internet Plus Blast

Until this week we had Comcast Business at my startup. We’re not demanding enough yet to need WebPass or MonkeyBrains, and we were paying $84/month for 16Mbs.

In terms of changing plans, I didn’t even need “a buddy” because Comcast Business and Xfinity are very separate organizations inside Comcast. I simply walked into the Comcast customer service center and signed up for a new Xfinity plan as a new customer, came back to the office, and I was up and running – from walking out the office door to getting back and online – in under 60 minutes with 100Mbs internet for $45/month.

That’s a saving of $500/year – not bad for an hour’s work. If you’re legitimately earning more than $500/hour for every hour you work every week of the year (sure you are), then you might not get cash value in savings, but you’ll also see time savings by having your internet more than 6x faster.

Comcast Speed Test 1

Xfinity for Cable and AT&T for Internet

My girlfriend was running Comcast for TV and Xfinity for internet, due in large part because her apartment building told her she had to use AT&T (or another DSL service?) for internet access. Her total bill was over $100/month. I thought the instructions about using only DSL were a bit off because she was using Comcast for TV, and sure enough, it was possible to move her over to Comcast. Because she was an existing customer, however, she was stuck with paying over $100 to bring it all together – not a great result.

Through making the change to Xfinity for internet and cable box, she’s now paying $39/month. There’s still some frustrations with stepping back to non-HD cable, but we’re working on fixing that (I’ll have an update in a part two post about TV specifically).

So, while it isn’t apples for apples, she’s now paying $50 (when you include Netflix and Hulu) for basic cable, HBO and stacks of other streaming all through a super cheap Chromecast in high quality – a saving of 50% for internet 10x faster internet and all the content you can stream.

Inside Sales Idiot Nominee: Emma(?) from Silicon IT Hub PVT LTD

A quick one from another set of off-shore outsourcing bottom feeders. While any LinkedIn user knows that these are pretty much the only messages being sent on the platform these days, this one was too funny not to share.

Highlights include:

  1. Emma spelling her own name wrong. Probably a tell that this isn’t really Emma.
  2. Unnecessary use of the PVT LTD descriptor of an Indian registered company – don’t these people realize this has become a red-flag in business solicitation?
  3. LOUD NOISES and other Caps In Strange Places.
  4. The best line I’ve read today: “implement this techno name of designs” (referencing Responsive Design, which they claim to have been one of the first to implement).

Enjoy the stupidity of Silicon IT Hub PVT LTD (nofollow applied).