How I Earned and Maximized the Southwest Companion Pass

Hey friends,

As many of you know, this past year Aisha and I have travelled to Cabo (2x), Seattle (3x), Cancun, Puerto Vallarta, Jamaica, Miami, Orlando, Vegas, Orange County, and LA – all absolutely free thanks to the Southwest Companion pass.

We’re going to Miami! 

I really hope you do this so we can be travel buddies. This year Aisha and I have already booked Miami, Coachella, Vegas, Portland, and plan to also hit Cancun, Chicago, New York, and Austin before the end of the year.


This is the best time to go for the Companion Pass

Right now is the *BEST* time to do this.  The regular sign-up bonus is only 25K points, and the 50K sign-up bonuses come and go. I have a valid referral link for the 50K sign-up bonus right now.

Because it’s the beginning of 2016, if you qualify for the companion pass now, you’ll be able to use it for the rest of 2016 and all of 2017 – that’s 22 months! 

If you miss this chance,  the 50K bonus will be back in a few months, but then you’ll only get to use your Companion Pass for ~15 months instead of 22.

You’ll need to block out an hour on a weekday during business hours to apply to both cards because you’re more likely to get fast approval during business hours.

Full Disclosure – I have 2 selfish reasons for wanting you to do this. First, I’m gonna make 5000 bonus points by referring you. And more importantly, now we can go on trips together!

Disclosure #2 – I earned the companion pass by opening a Southwest Premier and Plus card. The Plus card doesn’t have a 50K sign-up bonus at this moment, so I’m going recommending the Southwest Business Premier Card –  something I haven’t personally tried applying for. That said, I’ve been researching this exact plan for Aisha to get the Companion Pass right now. We didn’t need her to apply this year, however, because I racked-up enough spending to get my Companion Pass renewed through the end of 2016.

Here’s the Math

You need 110,000 points in one calendar year.  You’re going to get 50K points for each card you open (once you hit a spending threshold). So you’ll need to spend another $10K on the cards once you open them. If you and your companion are diligent about putting *everything* on these two cards for the next 3 months, this should be very doable. Talk to me and I can give you some ideas.

Let’s get started

1 – Apply for the Southwest Premier Card 

They don’t let me post the link on the internet. So I’ll need to email you the application link through their tool. Here’s some context:

You’ll likely get approved for the first card and the second you’ll be declined or “pending review.” That’s okay. You’ll call their “reconsideration line” and probably get approved instantly. I’ll walk you through what to say.

By applying for 2 cards on the same day, you’re not going to get the same ding to your credit score as opening them on separate days, because to the credit agencies will look like you’re shopping around for 1 new card.

2 – Apply to the Southwest Premier Business Card

Listen, don’t get hung up on the fact that you don’t own a company. Their requirements are really loose, and you’re going to answer truthfully. Read this blog post beforehand – it lays out exactly what the application is going to ask for, and how to answer truthfully but in a way that allows you to qualify for the card.

You’ll need to do 30 minutes of prep so you can answer any questions about what your business is. In Aisha’s case, her business was going to be renting out our apartment.

3 – If you don’t get instant approval, call their reconsideration line

I had to do this last year, and it seems like it’s pretty normal.  Here’s what you need to prepare for, and plan on saying when you talk to the customer service rep:

If you’ve done business with Chase in the past -e.g. checking account, other credit cards like Chase Freedom or Sapphire, make sure to mention this! Shows that you have a history of being responsible.

Next, tell them that you’re trying to get Southwest sign-up bonus, which is why you’re opening the card. This signals you’re about to spend a lot of money – and – make them a lot of money.

Next, Chase may not want to extend thousands of dollars in new credit to you if you already have a couple cards with them. So tell them you’d be open to them lowering your credit limit on a different Chase card if they’ll approve you for low limit on this new card.

Finally, you’ll need to have details on your business prepped and ready to share in case they asked. Read this and write down your answers beforehand.

You might get approved for the Business Card instantly. Or they may notify you within 30 days. If you didn’t get approved for the Business Card, all is not lost. I’ve got a backup plan for you. Skip to “Backup Plan” below.

5 – You’re approved! Now have to spend $10K more to achieve your goal.

Let’s break down that math:

  1. Spend $2K on Premier card. Earn 2K points for that spending. Earn 50K sign-up bonus.
  2. Spend $2K on Business Premier card. Earn 2K points for that spending. Earn 50K sign-up bonus.
  3. Total so far = 104K points
  4. Spend another $6K
  5. Reach goal – 110K points

Remember there’s a delay. Let’s say you spent the money in Jan. It shows up on a Feb 15th bill. The Feb 15th bill isn’t due till Mar 15th. So the points might not post till Mar 30th. Your mileage may vary, but with my Chase Marriott card, as soon as I hit the spending threshold I paid-down my bill a few weeks before it was actually due, and the points did post much quicker than I was expecting.

6 – BOOM. You’re done


It’s happening!

7 – Maximize the Value of the Companion Pass

Remember, the way to maximize value is to book your flights with points, and then add your companion, who flies free. The alternative way, that is less valuable, is for you to buy your ticket with dollars, and then your companion for free.

Be disciplined. From now till when the pass expires, prioritize travelling to cities Southwest flies to. Now’s the wrong time to plan that Euro trip. 110,000 miles is probably enough for your first 5 trips, but after that, you’ll need to start earning more points. So I made Aisha an authorized user on the card, and we each put all our spending on the Southwest cards for the year.

Focus on the high value destinations. Yes, Southwest can get me from SFO to LA. But since they acquired AirTran they now fly to the Bahamas, Cancun, Cabo, Puerto Vallarta, Belize, Aruba, Jamaica, Dominican Republic, Puerto Rico, and more! That is why Aisha and I have been to Mexico 4 times in 1 year.

Double and Triple points on some purchases. (This one is a bit lower leverage on your time, but I wanted to share it.) If you do spend money on Southwest flights (I avoided it), obviously put those on your Southwest card, as you get 2X points.  You also get 2X points with their hotel and rental car partners. But if you do online shopping, you can rack up a LOT of points. Southwest has an online shopping portal. The idea is online retailers like ASOS want you to buy stuff on their site. So they’ll give an affiliate kick-back to Southwest if you  click from the Shopping portal into ASOS’s websites and buy something. Southwest, then, will give you that kick-back in the form of additional points-per-dollar-spent. Aisha loves shopping at ASOS. So I would always have her start from the Rapid Rewards Shopping Portal. Buy the thing she planned to buy anyway. Pay for it using the Southwest card. And then we’d see on our next statement that $100 in ASOS spending was actually going to net us 600 miles.



Here’s some stuff that you might wanna know for more context

Backup Plan

So you’ve applied and been approved for the Southwest Premier card. But not the second card. This can still work! You’re sitting at 50K points. You need another 60K. So it’ll be more complicated, but you’ve got a couple options:

Option 1 -Use Hotel Points You already Have!

A lot of people think they can transfer Chase Sapphire or other points to Southwest. These transfer points won’t count as companion-pass-qualifying miles. But Hotel points will!  So if you have a ton of Hotel points, you can cash those in. The conversion rate isn’t pretty. You’d need 140K Marriott points to get 50K Southwest miles.

Option 2 – Open a New Hotel Credit Card  AND a Southwest PLUS Card

I opened a Marriott card. Got a 70K point sign-up bonus. And earned the companion pass for year 2.

Option 3 – Open 1 card, and spend $35K 

If you have some big purchases coming up, or can put work expenses on your card, this is actually a much easier option. It may be a slower option, so rather than having a companion pass for 22 months it might only be for 18 months, but that’s still a huge value.

Should You Keep these Cards Forever?

I asked myself this question a few months ago. The answer is probably not forever.

Pros for keeping ’em:

A – More credit extended, less utilization. If you have a $100K credit limit across all your cards, and you only rack up $5K of spending each month, your credit utilization is 5%. That’s really low! That’s really good! If you close a card with a $20K limit, and still spend $5K each month, now your credit utilization goes up to 6.25%. That’s worse.

B – 10-15 lines of credit is considered good for your credit score. In my case, I had very few credit lines (I had never had credit cards until the past few years) so my credit score was weak, and keeping these cards open is good for my score.

C – One of the most amazing things about the Companion Pass is you don’t trade-in those 110K points for the Pass. You earn the Pass, and then you get to keep & use those 110K points. So this entire year, I’ve been booking my flights with points, and Aisha’s flights are free with the Pass. Once I burned through the enormous 110K stockpile of points, I started keeping all my spending on the Southwest cards so I could earn more points, so I could travel completely free even more.


These two cards both have $100 annual fees. So about 11 months after opening the cards, you might want to consider cancelling 1 or both to save that money.

Regarding point C in favor of keeping the card. What i realized is that for earning the pass you have to spend on your Southwest card. But for earning points once you have the pass already, the Chase Sapphire card works much better because I earn 2X points on travel and dining, which then transfer to Southwest miles at a 1:1 ratio.


Veterans Deserve Careers, Not Jobs. Silicon Valley Can Help.

Transitioning from military to civilian life can be an agonizing process for many veterans. While the overall unemployment rate for post-9/11 veterans is 7.2% (1% higher than that of civilians), what’s truly alarming is that for male veterans ages 18–24, the unemployment rate is a staggering 17.3%.

According to David Molina, founder of Operation Code, something has to be done. “Our veterans have served their country, and they deserve a path to a career, not just a job.”

The Difference Between a Job and a Career

Chris Kibble, U.S. Air Force Officer

According to transitioning U.S. Air Force Officer turned web developer Chris Kibble, “lots of veterans leave the armed forces each year. Many feel compelled to follow the traditional post-military career paths — defense contracting, airlines, security firms — because they assume these are the only options open to them.

Kibble after completing his final flight

Few veterans take advantage of the military’s career transition resources because the vets don’t know what’s available or they fail to navigate the bureaucratic benefits system.

Johnathan Smith, U.S. Marine Corps

Johnathan Smith was an administrative specialist in the Marine Corps from 2005–2009. According to him, “we had jobs that didn’t translate to careers in the civilian world. When I got out, no one was hiring someone with no degree and 4 years of experience doing admin work for the military.” Smith ended up working at a hotel for $13 per hour, supporting himself and his new wife, while going to school.

Robert Cox, a member of the Marine Corps Reserves, described his friends coming off active duty: “The majority are doing manual labor jobs after they leave the military because it’s the closest to what they know.”

The GI Bill Doesn’t Solve the Problem

Robert Cox, U.S. Marine Corps Reserves

Even though some vets are eligible for paid tuition under the Post 9/11 GI Bill, many choose not to go to college. “They see kids being bankrolled by their parents. They just can’t relate to these college kids,” said Cox.

Cox had taken a few computer science courses at the University of Alabama, but dropped out due to some family struggles. The exposure stuck with him and he dabbled in low-touch online coding resources like Treehouse. It introduced him to coding concepts and piqued his interest in web development as a career path. When he wanted to get serious, he enrolled in Bloc, an online, mentor-led coding bootcamp for people pursuing careers in web development. He combined a veteran’s scholarship from Bloc with a loan from Navy Federal to pay for the course.

“College computer science programs are outdated. You have to go with what’s hot, what’s being used now, and what’s scalable.”

Smith says, “College computer science programs are outdated. You might learn something in school but then the company you want to work for isn’t using that particular language. You have to go with what’s hot, what’s being used now, and what’s scalable.”

How Silicon Valley can Help

There are two major changes Silicon Valley needs to make to support our veterans. First, we must challenge leading tech firms to publish a more holistic diversity scorecard that includes underrepresented groups such as veterans. Second, leading tech firms need to build diverse pipelines to source technical talent. While startups often need experienced engineers who can hit the ground running, more established companies, who already have robust internship and college recruiting programs, must source some of their candidates from other sources.

Members of the military spend years building hyper-specialized skills and networks that do not easily translate to opportunities in the civilian job market. According to Cox, “many of them don’t even know this startup scene I’m working in now even exists. But the people I know would thrive in the tech industry. They can work under extreme pressure.”

Of getting into tech, Kibble says “I’ve known for a long time that I wanted to transition into the tech world. But I lacked the fundamental skills to make me competitive in the marketplace. I went for a year or two trying to “teach myself” how to code on nights and weekends while on active duty. The results were not inspiring.”

According to Kibble, “That’s where bootcamps like Bloc come in. They present new career possibilities for veterans, especially for those that didn’t serve in a technical career field. And for those still on active duty, there is a part-time, online option. My instructor was a fantastic teacher. He gave me feedback that sped-up my learning immeasurably. Those skills led directly to my first job offer as a junior Rails developer.”

Those skills led directly to my first job offer as a junior Rails developer.

Kibble continues, saying “if you’re a veteran, and you’re committed to transitioning into tech, I’d definitely consider a bootcamp. It’s not a 100% guarantee of a job — don’t believe anyone who tells you that. And the process of learning to code is frustrating at times. But vets have the discipline needed to succeed as programmers. And if you put in the effort, you’ll open up a new world of career choices.”

What We’re Doing This Veteran’s Day

Veterans have already served their country. To honor their sacrifice, Bloc and Operation Code are offering all veterans a $1,000 tuition credit toward Bloc’s Web Developer Track. The remainder of the tuition can be financed.Learn more here.

About Operation Code

Operation Code is on a mission to trailblaze a new career path for military veterans in software development and coding by providing access to efficient and practical coding education, mentorship and employment services.

How You Can Help

We are looking for corporate sponsors to help defray more of the tuition cost for veterans attending the program. More importantly, we are looking for corporate partners who want to offer paid internships to graduating vets. If your company is interested in sponsoring or hiring a vet, please contact

How to Jumpstart a Coding Career

Note: this post originally appeared in VentureBeat

As the world continues to topple tech breakthroughs over and over, the demand for qualified programmers to fuel the industry grows exponentially. Not a shocking discovery — after all, those time-saving (or time-consuming) apps didn’t manifest on their own. However, what is shocking is that despite the high demand for tech jobs, there are still people who despite keen desire, are stumped on how to get a leg up in the business.

Either intimidated by the perceived difficulty in learning to code, or financially stretched to support full-time college enrollment after a certain age, would-be programmers are missing out on following their dreams. And learning to code solo isn’t a viable option — it just doesn’t prepare you for the everyday challenges that arise from programming. So, what’s the solution? The answer is actually pretty simple: Coding bootcamps.

Across the nation, coding bootcamps are popping up and providing young tech lovers with the education necessary to mature their skills at a professional level. With a determined focus on programming and seasoned pros assigned for one-to-one mentoring, coding bootcamps are far more beneficial to students than universities that pass the craft off as a general elective. Furthermore, some coding bootcamps provide low-paying alternatives and offer discounts for minorities and women. Not to mention, 75 percent of those who graduated from coding bootcamps found full-time employment with an average salary increase of 44 percent.

Coding bootcamps aren’t just a leg-up for students, but valuable for entrepreneurs as well. It helps educate them on how to build the products they want in a timely fashion, along with introducing them to promising coders to join their company. What’s a better opportunity to find fresh and diverse minds in the industry than the training programs they’re emerging from?

In this webinar hosted by Dave Paola, Cofounder and CTO of Bloc, and Prasid Pathak, Bloc’s Director of Marketing, you’ll learn more about the benefits of enrolling in coding bootcamps — benefits that range from financial gain for you or your start-up company, to bettering your skills as a programmer — and the differences between them. It will also show you how to work on your raw ideas after graduation and successfully promote them to your employers. The coveted life of a programmer is actually within reach.

Watch the recorded webinar here

What I learned building a sales org from the ground up

I had a decade of experience in growth marketing. In 2013, I became the first sales person at an early stage startup. Here’s what I learned in my first three months.

Finding the Right CRM for the job

I started out keeping track of students or “leads” on a spreadsheet, but soon realized I ought to find a CRM tool. We’d used Zoho at SoFi (much to the dismay of every person at SoFi who came in contact with Zoho), so I knew to stay away from that.

I had been introduced through a friend to the co-founder of Pipedrive, so I spent a day testing that out. I was really drawn to the visual way of managing a pipeline — dragging-and-dropping leads from one stage to the next. And as someone who wasn’t coming from a sales background, this struck me as easy and intuitive.

The obvious choice would have been Salesforce. Everyone was doing it. I’d worked with the Salesforce before, and (hindsight being what it is), I now know that a year later we did eventually embrace Salesforce.

But as an early stage sales lead — with a team of just me and one college hire — I realized that getting Salesforce up and running would be a tremendous burden — a steep learning curve I didn’t have time for.

Instead we chose — and it was one of the smartest decisions I’ve made. Close is a little less intuitive than Pipedrive, but very well designed, powerfully simple, and integrates mail-merge. In some ways it strikes me as the Apple of CRM tools — it strips CRM away to it’s core and leaves out a world of functionality that bloats Salesforce (and makes Salesforce so powerful in larger organizations).

Thanks to that decision, we had a CRM tool up-and-running with days rather than weeks, and we could get down to the business of closing deals.

Give yourself over to the machine

In my first month as a sales guy, I would grind every night, working my way down to that elusive inbox zero. And I would manually keep track of who needed following-up with. It was starting to drive me crazy, and I realized I would lose my mind trying to remember each lead before they fell through the cracks.

There’s a famous productivity author named Sally McGhee — she worked with David Allen (author of the Getting Things Done). McGhee’s productivity methodology talks about the simple idea — that tasks out to be organized in order of importance, and yet millions of us spend our day living out of our inbox — a list that is instead sorted in reverse-chronological order. It’s a tiny but powerful insight that’s stayed with me.

Eventually it hit me: there was no way to stay on top of all the correspondence. I had to give myself over to the CRM. We developed a system of buckets. A bucket for new leads. A bucket for leads that we’ve reached out to once. Twice. Three times. A bucket for after we have a good conversation. And my goal became to just move leads from bucket 1 to bucket 2. Rather than a top-down approach of trying to follow-up with individual people, my day became a bottoms-up approach of emptying each bucket at some regular cadence, and trusting the system to prevent leads from falling through the cracks.


Two years later, I have a team of four inside sales folks and three marketers. After a year using, we finally began bumping up against it’s limitations, and transitioned over to a much more robust (though cantankerous) sales stack using Salesforce, Marketo, and Our bucket theory is still very much alive, and it’s still how we think about keeping leads moving through our sales funnel.

If you have a sales team of 1–2, and no one can articulate a strong reason you must have Salesforce, I strongly recommend You can have it up and running in a few hours, it replaces both Salesforce as well as a sales automation tool like YesWare, and at an early stage startup, driving bookings quickly is likely more valuable to you than spending two weeks configuring a complex Salesforce instance and overcoming that steep learning curve.

Keep your sales process as simple as possible. As few stages as possible. As few fields as possible. You can always make it more complex later. Once you have the bookings to justify investing in better tools, you can easily migrate data out of into Salesforce. Just get something up and running. And start closing.

The biggest downside to loving your job

For me, the biggest downside of loving my job the last two years has been it sucks-up every moment of free time and professional energy, and I stopped blogging.

It’s not that I couldn’t have made time to blog – but I think as long as I was learning so much at work, the thirst to write was quenched.

I’m also not nearly as good at short-form as I am at long-form. But I’m going to try to be better.

So, I’ll leave you with this.

Mind boggling; this press of words

Apparently 19% of the whole damned internet runs on WordPress.

There’s another stat that wordpress powers 48 of Technorati’s top 100 blogs, and that’s fine and dandy. but 19% of the whole internet? That goes far, far beyond just blogs.

WordPress, if you can believe it, powered most of Bloc’s consumer facing website when I worked there. WordPress powers some of the most trafficked and well designed sites in the world. It’s because it’s very powerful. And it’s often far easier and effective to leverage WordPress than to build a homegrown CMS.

We are struggling with that exact issue right now. And as much as I can empathize with those that look down upon WordPress, I’m a very big believer in being good at one thing – and licensing the rest. I have gotten Bloc very far, very fast, with very few resources, by always remembering that we’re in the education business, and not, for example, in the CRM-building business. Rather than building something, we gave ourselves over entirely to Marketo and Salesforce. It was painful. But today we have powerful reporting and analytics built on top of data coming from Marketo and Salesforce. And that reporting is democratized in a way that many users have access to it. Most of the time, if I want a new feature, we can add it within hours, not weeks. And without the help of our most valuable resource – engineering time.

The same would be true of WordPress, except engineers hate wordpress.  In my case, it’s a love hate relationship I can’t get rid of.

#LifeHack to adding Cream & Sugar

#LifeHack to adding Cream & Sugar

Have you ever wanted to add cream and sugar to your coffee, but you didn’t wanna take that nice plastic lid and set it down on a gross looking counter? Here’s my solution:

1. With lid still on the coffee cup, put stirring rod into the sip-hole of the lid
2. Now, take the lid off, and let it hang off of the side of coffee cup like so
3. Add Cream & Sugar to taste
4. Stir
5. Put lid back onto cup
6. Throw away stirrer
5. Drink. Caution: Beverage may still be hot