Raising Rich Kids

How are you going to avoid raising shitty kids?

– A friend

In April 2019, I sold a majority stake in my startup to private equity. The news made local headlines and our family’s financial situation changed overnight. Soon afterwards I had celebratory drinks with a friend who is a serial entrepreneur and has sold multiple companies. He said to me, “Now that people know you have wealth, be ready for all of the awkward things they are going to say to you.”

Several months later I met up with a friend I used to work with. I don’t remember if these were literally the first words out of his mouth or not, but they very well could have been: “So… how are you going to avoid raising shitty kids?”

The path to having rich kids

Wow. That caught me off guard.

(And to that friend — if you are reading this — I know you’re going to feel bad and reach out with a flood of apologies. Don’t. Only a true friend would feel comfortable saying something THAT awkward right out the gate!)

It was a valid question that I didn’t have a solid answer for in the moment. And I sort of brushed it off.

I told him the same concern would have probably existed even if I never ventured out as an entrepreneur. My wife and I are incredibly blessed that our parents and grandparents put us on a trajectory to live a much more comfortable and luxurious life than they did. Had I stayed put as a software engineer, we would now be two decades deep earning dual-incomes while climbing the ladder at large technology companies. By all measures I’m sure we would be living an extraordinarily privileged life. When I imagine the potential lifestyle in that scenario, I have to wonder: how much less would we need to worry about our kids being spoiled if we simply lived in a 4,500 square foot house and drove less expensive Teslas?

But I suspect my friend was imagining some particularly dramatic changes in our lifestyle.

And to a degree, he was right; there are some substantial privileges our kids have encountered these past five years– even in comparison to the other very successful, high-income families all around us. The house we live in, the travel experiences, the way we dine… Varsha and I no longer hesitate on experiencing the “best of” when it comes to the things that truly matter to us, and our kids are usually right there by our side.

Our change in wealth has certainly impacted many of the “big” purchases and “big” experiences in our lives. But, in all of the “little” ways, I like to think that we are exactly the same people as we were before. The kids still see us working our butts off morning through night — even if these days many of our hours are spent pro-bono or to help a non-profit, rather than worrying about our own retirement savings.

Ah, little vs big. I think I found the answer to my friend’s question. I’ve always operated by the belief that it’s the little things that make the most important difference. And how we raise our kids should be no exception.

Actually, there are no rich kids

A few months ago we were having lunch at home when our youngest, Asher, casually asked us, “Hey guys, are we a little rich?”

Our answer started with, “Well, Asher, you are certainly not rich. You’re just a kid!”

We then gave him a brief talk about why it’s important to always work hard in life, take chances when you truly believe in something, be grateful for things to work out (because they don’t always), recognize that many people don’t have what we have (but they still have every reason to be as happy as we are), and even when you have more money than you need, remain thoughtful about how you spend it.

I don’t know how much that one conversation will stick with him. But there are countless little opportunities to impart these same messages each and every day: the ongoing grind of household chores, the chance to save $3 on a purchase at Target, when something breaks in the house (which happens a LOT in a big house!) and we need to roll up our own sleeves, and of course, each and every time we interact with another human being.

These little interactions, little decisions, and little events are like the ongoing force of gravity; always present as an opportunity to keep our kids grounded.

I’ve certainly been far from perfect in many of these circumstances but to-date I could not be more proud of the character and values embodied by our kids. After all, it’s been five years since our financial picture dramatically changed…. and he’s just now starting to wonder, are we a little rich?

The Intentional Sales Funnel

Intentional sales funnel

I frequently encounter B2B startups who are struggling with scaling up their sales motion. Not that surprising, eh? We know sales is hard!

What is surprising is that many of these companies have grown past $1M ARR and seem to already have all of the right pieces in place. We’re talking… a CRM with sales stages, pipeline review meetings, stage-based forecasting, and documented processes and expectations for their reps. Yet their sales motion feels weirdly unreliable.

When I dig in with the founder (or head of sales) I usually end up suggesting that they look much more closely at what’s really happening at each stage in their sales funnel. It’s not that they have the “wrong” stages in the funnel. The problem is the disconnect between the meaning of each stage versus what the reps are actually saying and doing. They are not executing on an intentional sales funnel. As an example…

Discovery meetings are for… product demos?

Most B2B sales motions have a concept of a Discovery Meeting early on in the sales funnel. At a basic level the point of this meeting is for the rep to 1) determine if and how the prospect can be sold to, and 2) obtain buy-in from the prospect to engage in the sales process.

But what often happens in reality at the Discovery stage? Reps are allowed to make a loose judgement call on when to switch into pitching the product. This usually means that reps run through a few high-level questions (as required by process) and then find any excuse to show the product demo. Repeat this across hundreds of opportunities and a half dozen reps and what do you get? A pipeline chock full of opportunities that exit the Discovery stage at wildly different levels of qualification and buyer interest. No wonder it’s hard to scale that sales motion!

Here’s what I tend to suggest:

  1. Take a step back and get crystal clear about the intent of each stage in your funnel.
  2. Implement mechanisms to help reps stay disciplined and focused on delivering outcomes aligned with the intent of each stage.
  3. Operate with my favorite sales process litmus test in mind (more on that below).

1) Stages of an intentional sales funnel

When I have this conversation with a founder I usually end up walking through a conceptual model of how I thought about the the sales funnel at my company. This isn’t exactly how we named or set up our sales stages in Salesforce. Rather, when I look I back, this is how I would describe the design of our sales process. I find that this conceptual model is generic enough to make sense for any B2B company and works for other types of sales too.

One key thing to notice below: the intent of each stage below is simple and to the point. A lot of sales process docs I’ve seen are seemingly well-written but the sales stages are described in long bullet lists of what the rep should be asking or trying to accomplish. I think that’s where things go off the tracks. While it’s important to support the rep with process details and talking points, you must ensure they remain laser-focused on the big picture intent of each stage.

Stage 0: Establish curiosity

Here I am referring to sales activities that precede opportunity creation, such as outbound calls.

Intent: Create enough curiosity in the prospect that they are willing to take time to hear the actual sales pitch.

What to include: Discussion around the problems the prospect might be facing, social proof of helping other similar organizations, and (optionally) lightweight discovery-like questioning to qualify the prospect.

What to avoid: Talking about product features and pricing, and anything else that resembles the full-on sales pitch. The only thing to sell the prospect at this stage is a sales meeting on their calendar.

Stage 1: Sell the problem

This stage in the intentional sales funnel comprises of the first real sales meeting with the prospect — which in B2B sales is typically the Discovery Meeting. In my opinion what happens at this stage has the potential to make or break the entire sale. In fact, I considered writing this entire blog post just about getting reps to execute really well at this one stage in the funnel.

Intent: Level set with the prospect on the existence and severity of the problem they are facing, and determine how you can best work with the prospect to help them solve it.

What to include: In-depth discussion about the problem the prospect is facing, your company’s expertise and knowledge related to the problem space, and how you can appropriately coordinate with the prospect to explore a solution.

What to avoid: A product demo prior to having a substantive understanding of the prospect’s pain, and without first getting explicit buy-in from the prospect to explore solutions with you. That last part is key. A prospect acknowledging their desire to spend more time with you is drastically better than throwing a sales pitch at them and then hoping that they’ll show up again for another meeting.

Stage 2: Agree on the solution

Once you have a shared understanding of the problem the prospect is facing, and alignment on working together to explore a solution, NOW it’s time to bring out the product.

Intent: Demonstrate how your solution can help the prospect easily/effectively/affordably address the problem they are facing, and get them to agree that your solution is the most appropriate solution for them.

What to include: The full-on sales pitch including the product demo, pricing, and purchasing process.

What to avoid: A one-size-fits-all sales pitch that you might deliver verbatim to another prospect. If you followed through on the intent of Stage 1 then you should be able to deliver and position the pitch in a way that is personalized and highly tuned to what will drive the prospect to take action.

Stage 3 (if needed): Ensure internal buy-in

If you are working directly with a single decision maker this stage might not be necessary. In our case, we sold to government agencies and the decision to purchase almost always required consensus amongst multiple stakeholders. To get to this stage it is imperative that your key contact is already fully on-board.

Intent: Support your key contact in driving internal consensus around purchasing your solution.

What to include: Whatever can best arm your key contact with creating internal buy-in with the decision makers. Ideally you would insert yourself in these discussion so that you can help drive the sale directly. Otherwise, if providing materials to support your key contact in doing their own internal selling, these materials should be personalized based on the discussions you’ve had with your key contact, while also positioned appropriately for the roles of the other stakeholders.

What to avoid: Continuing to sell and (risk over selling) your key contact, and doing anything that introduces new complexity for your key contact.

Stage 4: Complete deal logistics

The keyword here is logistics. At this point, the actual “selling” should be done. What stands in the way of closing the deal might be a legal contract, IT or security assessment, or some other procurement-related checklist item.

Intent: Help the prospect buy your solution as quickly and as easily as possible.

What to include: Information and materials that simplify and/or avoid logistics. If you notice common hang-ups across the pipeline, re-design this part of your process to try to avoid them. In our case of dealing with the hurdles of government procurement, we iteratively revised our pricing, terms of service, and sign up process to help most of our customers refrain putting out RFPs and even avoid having to formally sign a contract with us.

2) Helping intention become reality

Alright, an intentional sales funnel might look nice on paper, but how do you actually change day-to-day rep behavior to stay true to the intent of each stage?

Training, monitoring, and 1:1 coaching are always part of the equation. I’m also a huge fan of using the CRM and other tools to help validate and enforce desired behaviors. One example is how we approached the Discovery meeting (i.e. Sell the Problem) stage at my company: we added a section in the CRM called “Discovery Outcomes” containing five questions. In essence these five questions required the rep to regurgitate their understanding of the pain-points faced by the prospect (as explicitly stated by the prospect) as well as the rep’s initial understanding of what it might take to sell the prospect. Doesn’t that sound more aligned to the intent of a Discovery Meeting than doing a product demo?

In 1:1s, call review meetings, and pipeline review meetings, sales managers could then use this information to determine if a rep was conducting effective Discovery meetings — and if not, work with the rep to improve execution at that critical stage in the funnel.

3) Operating with a litmus test

Finally, how do you assess if your sales process is well-designed and being followed in a disciplined and consistent manner?

At any moment, you should be able to take the opportunity pipeline from one rep and hand it to another rep on the same team, with the new rep having everything they need to effectively carry forward each opportunity from the stage it is currently in.

-Anil’s fave sales process litmus test

This litmus test encompasses a lot of things including the design of your intentional sales funnel, how well reps are adhering to process, and the quality of documentation in the CRM. And while flipping pipelines willy nilly from rep-to-rep might sound like a pipe dream (pun intended), let’s take it back to the intent of this post: the closer your sales process gets to passing this litmus test, the more likely you can scale it.

Hiring and the AAA Player

In the summer of 2003, before I started my senior year at Georgia Tech, I found myself pitching to a room full of executives at IBM Headquarters in Armonk, New York. I was finishing my internship in IBM’s Extreme Blue, a startup-esque program designed to lure top talent into working for IBM.

Immediately after my pitch an executive walked up and asked if we could meet the following morning.

That next morning he was pitching me. He told me his hiring philosophy and the attributes he looks for in the best candidates. He said, “attitude, aptitude, adaptability, and experience — in that order.”

He emphasized to me that even though “experience” is obviously an important factor in making a hiring decision, it was a distant fourth. And he had seen enough of the first three attributes to make me an offer to work anywhere within his group.

I was taken aback. It meant a lot that a Director of a product group — a 3rd-level manager in IBM — had hand-selected me. I accepted the job a few weeks later even though I had just started my senior year and still had other interviews (including one with Microsoft) pending. I didn’t dare negotiate the offer either as I didn’t want to ruffle the relationship with this executive.

By the time I joined IBM full-time the following summer, he had already moved on to work for another group. Such is IBM.

The AAA hiring framework

Although I never crossed paths with that executive again, his hiring philosophy stuck with me and I think it’s mostly right. Especially the “in that order” piece. Looking back I’d make a couple of tweaks:

  • Pull “adaptability” into Attitude
  • Replace “experience” with Accomplishments

This gives us a simple mnemonic for evaluating hires for any role in any company: AAA

It starts (and ends) with attitude

I think of attitude broadly as how a person approaches things, which then drives their behaviors.

  • How do they approach work?
  • How do they deal with challenges and opportunities?
  • How do they treat the people around them?

The attitude check is as much a check against company culture as it is an evaluation of personality traits that dictate performance. To me getting this right is a non-negotiable: you must be excited about a candidate’s attitude in order to hire them.

Aptitude is essential but comes second

Of course, you have to determine if a candidate has the skills and abilities to do the job. But in this framework a candidates ability is only relevant if their attitude is a fit.

Let accomplishments validate your assessment

We all know that it’s bad form to fill out a resume by only listing the responsibilities you had in each role. Your resume really needs to convey the impact you made. In the same vein, I’d rather think about a candidate’s accomplishments than their “experience”.

Nonetheless, I still put accomplishments last in the order of evaluation. In fact, I’ve learned that you have to be careful not to let a candidate’s past accomplishments override your own evaluation. There’s a lot of factors that go into why a person might have encountered success in a past role, and I believe that you first have to trust your own direct assessment of the candidate. In other words, their past accomplishments should mostly serve as a validation of how you rate their attitude and aptitude.


There’s a lot more that can be said about making a hiring decision. For example, there are a handful of personality traits (from the Attitude category) that I always look for. There are also some factors — like diversity — that don’t exactly fit the AAA acronym, but can be very important and influential when trying to select between multiple qualifying candidates.

But I like the simplicity of AAA as a high-level framework and the organizing principle it provides. Attitude, Aptitude, Accomplishments — in that order.

Back to the blog (I quit my job round #2)

It’s been 3,379 days since I last posted on this blog. A lot has happened in life since.

Here are a few personal updates about what happened after I last tried to compare building a startup to raising a baby in 2013:

  • I became a serial father. Our second son, Asher, was born in 2015. He’s now almost eight and is an amazing kid full of happiness, creativity, cleverness, and love. And Dilan has since grown into an equally wonderful 10 year old.
  • My startup idea worked! Our software has now helped thousands of cities, counties, law enforcement agencies, and other government entities more transparently engage with citizens. We even took on the President of the United States as a client…and yes, that other President too.
  • I quit my job, again.

OK, this time was a little more glamorous than the job quitting that launched this blog. Here’s what I wrote about it in late 2019 to my friends and family on Facebook:

Eight years, ten months, and eight days ago… I wrote a post on my personal blog called “Call me crazy. I quit my job.”

Well, call me crazy again. But this time is different.

In December 2010, I stepped away from IBM to chase a dream. Somehow, and unbelievably, I have had the great fortune over the last eight years to fully realize and surpass that dream.

It wasn’t easy. To be honest, it was absolutely grueling. But it was led with purpose and more rewarding and fulfilling than anything I could have ever taken on.

The company I founded continues to grow rapidly and amplify its impact on the world. And I am honored to continue to be a part of its story.

Like in 2010, this was my decision and exactly the right one for myself and the people I care about most — which now includes nearly 70 people in downtown Durham!!

I am deeply, deeply grateful to all of you who have supported me throughout this journey. Thank you. The greatest fortune I’ve had in life is the opportunity to spend my time with extraordinary people — and none more extraordinary, inspiring, and supportive than my partner in life, Varsha.

I don’t know exactly what’s next, other than pursuing what feels like yet another incredible dream: spending as much time as possible with Varsha and our two super sweet, rapidly growing boys. After all, I’d be crazy not to 😉

So why bring this decade-old blog back to life again? I know that Google bot is likely to be my most avid (and perhaps only) subscriber.

That’s why… I’m doing this for me.

Yes, there is hope that others will occasionally find value on this blog, and perhaps I can even use it to build out my personal brand. But more than anything, I’m at a point in my life where I kind of want to restart the cycle; to go back to where I was (in a professional sense) in 2010. Exploring, building, and journaling the journey. I am the “archiving guy” after all.

Because when I look back, I see now that this sparsely populated blog was an important outlet for me; it served as a personal (yet public) ledger of the growth, progress, and learnings I experienced over a time period during which I often felt like I was failing and flailing.

I don’t know yet if I will start another company like ArchiveSocial. But I am itching to find my next purpose in life and to get back to creating value in the world.

In the meantime, some topics I might share perspective on using this blog:

  • Hard founder decisions, like choosing to sell a company and stepping back as CEO
  • Life after exit — including all the stuff (good, great, bad, & ugly) you encounter but nobody with wealth and professional freedom talks about because your life is supposed to be perfect
  • The marathon-sprint of raising little kids while pursuing demanding careers (and how to be a better husband)
  • The entire basket of learnings from scaling a company from $0 to over $10M in annual recurring revenue — including some fun and crazy stories
  • Figuring out what’s next when (conceptually) you can spend your time on almost anything you want to

To my friends, colleagues, and family who might run across this post: let me know if any of these topics grabs your attention. I might write about it here. Or at the very least, I can credit the relaunch of this blog for motivating us to grab a beer.

Raising a baby vs raising a startup

A friend of mine recently asked, “What do you find the same about raising a baby and building a company?” To be honest, the question caught me off guard. It felt like a question I should easily be able to answer, but I kept struggling to come up with a decent response. Each is a time sink and will destroy your sleep, but saying “you get busy” or “they’re both hard” felt like lousy responses.

There is definitely a process of learning involved in both fatherhood and entrepreneurship, but to me, they are still very different. Figuring out what works for your child takes a bit of trial-and-error, but the general practices are well known and eventually things fall into place — even if it means having to try over and over, or waiting until your baby gets older and matures. Our first child has been a crazy challenge, but given that we as humans owe our entire existence to cave people, I’d say that parenting is still a relatively intuitive practice and hard to completely screw up.

Entrepreneurship, on the other hand, does not come quite as naturally. It’s a process of learning that requires you to challenge, and potentially disregard, what you thought you knew. You have to question everything, and you’ll often find yourself on a lonely island on which everybody is questioning you. Even with the right methodology, knowledge, and passion, you might just be at the wrong place at the wrong time. In other words: babies generally grow and thrive regardless of parenting styles, whereas startups tend to fail even when led by strong entrepreneurs.

Reflecting back on my friend’s question, I realize now that maybe I was too caught up in the mechanics. Yes, progress might not come as automatically with a startup as it does with a baby that is naturally growing, but there is a way in which the two are very similar: it’s the manner in which you approach them. Here’s the best way I can figure out how to say it:

Raising a baby and raising a startup both require making difficult sacrifices in order to enrich your life in a way that would otherwise not be possible.

Having a baby changes everything. We barely sleep, go weeks without watching TV, and generally can’t do anything on a whim anymore. It requires constantly putting someone else ahead of our own selfish desires. Yet, it’s completely worth it. There is a type of love, and a part of life, that I never knew existed until we had Dilan. And I can no longer imagine life without him.

Similarly, quitting a good job to start a company can be a a brutally challenging experience. It’s the act of trying to create something out of nothing, and there are a million ways you can fail. It’s the choice to be continually uncomfortable. I really believe it is the hardest thing I could have chosen to do. Yet, it’s also incredibly fulfilling. It gives me a tremendous sense of purpose and satisfaction. And I can not imagine spending my life doing anything else.

When I think about this way, I realize how incredibly fortunate I am to be able to answer my friend’s question.

Mixergy Megatip: Tim Ferriss on being an outlier

If you have heard about the book The 4-Hour Workweek then you probably know who Tim Ferriss is. You might also know about his other books: The 4-Hour Chef and The 4-Hour Body. Entrepreneurship, cooking, and physical health are three very different topics. From the outside, some folks might look at Tim’s books — at least the latter two — and assume they are gimmicks. After listening to a relatively recent Mixergy interview of Tim, I no longer have any doubt: Tim is brilliant. And he is legit.

Tim’s interview is one of the best Mixergy interviews I’ve listened to. Since it was supposed to be about his new book, and my wife Varsha and I often think of ourselves as amateur chefs, I had lined it up for a road trip together to Charleston. Although the interview barely covered the book itself, Varsha and I were in stunned silence soaking it in. There were a number of huge take-aways from the interview, but there is one that has stuck in my mind more than any other; it’s the secret of how Tim is, time and time again, able to master anything.

We’re not all born superstars

The most obvious and intuitive approach to becoming better at something is to imitate the best. To most of us, this means copying the superstars. For example, if you want to become a better golfer, you might try to mimic Tiger Woods. If you want to be an Olympic swimmer, why look any further than Michael Phelps? Tim implies that this is a mistake. Tiger Woods, Michael Phelps, and most other superstars were born with natural talent and ability that very few of us possess. There is a reason why so many professional athletes grew up dominating multiple sports in their youth.

Tim’s advice? Find the outlier. Look for the person that probably shouldn’t have made it, but did. Keeping the sports analogy going, you might want to learn from John Stockton — not LeBron James. The person who succeeded despite a lack of natural advantages. The one who had to take an unconventional approach, figure out some tricks, and take some shortcuts. The one who had to find some way to do what nobody thought they could do. It’s likely that you will benefit more from studying his or her approach, than by copying a natural-born superstar.

The Mixergy interview with Tim is full of several other awesome take aways, like how your should really apply the 80-20 rule, and why systematizing everything actually creates more freedom in your life. If you are still doubting that Tim could actually become an expert at so many different things, then all the more reason to listen to him. He might be the outlier you need to imitate. Listen to the interview here.

How to hire an intern for your startup

The first two “hires” for my company were two part-time interns. I was drowning in responsibilities as a one-man-show, and one of my advisors told me, “Stop trying to do everything yourself. Just hire an intern for your startup.” So I did. I remember posting the position and being blown away with 40 resumes within the first day. I was even able to hire my top two candidates. Sounds like #winning, eh?

In reality, I was successful at hiring those interns but did a fairly poor job at orchestrating the actual internship. We’re now on our fifth intern in the past two years, so I thought I’d share some tips to consider when you think you want to hire an intern for your startup.

Tip #1: Don’t hire for an internship. Hire for a project.

More than anything, here is where is I screwed up those first two internships. It’s really tempting to have a smart, cheap, and eager resource willing to help on anything and everything you might throw their way. Don’t be fooled. If you are in a strtup, chances are that you are way too busy to come up with new tasks and projects on a continual basis. You might think that you can hire a intern for your startup to take on all of the stuff you can’t get to, but what you are really doing is just trading work. You’ll spend substantial amounts of time dictating those tasks to them and reviewing the results. It’s also likely that “come up with new stuff for the intern” will keep falling to the bottom of your TODO list, which really ruins the experience for both you and them.

I fell in this trap with those first two internships, and once again with one of our subsequent internships. The internships were not a waste by any means: all three of those interns made huge contributions, and I believe they gained a lot from the experience as well. It was just kinda painful.

The better approach is to come up with a mid-sized project that will last about 6 weeks and can easily be handed off to someone else. Ideally this project will have some high-level goals and requirements, and can be broken down into several sub-projects and tasks. This allows you to invest some time up-front and them mostly guide and delegate the rest of the way. As the intern makes progress, the next set of tasks and projects naturally become obvious. Why 6 weeks? Hey, if you can run about that long with one project, it’s easy to stretch it a few more weeks and end your brilliant, industry-standard “two month internship”.

In fact, I’ve decided that the only time we are going to hire an intern moving forward is when we can identify such a project. It makes sense when you think about it: let the work dictate the need for an internship, rather than the other way around. Starting with a project focus is also critical in determining the exact skill-set you want your intern to possess when you are recruiting.

Tip #2: Poke the career center for an email blast.

Assuming that you are hiring interns from local colleges and universities, it’s extremely helpful to have a contact at the respective career centers. We have some great schools in the Triangle but I particularly have great luck working with UNC. The key is to go one-step beyond just posting the job on the online career center. After the job is posted, reach out to your contact and ask them to email blast the student body. The resumes will start rolling in if the career center is willing to put your job posting in every (applicable) student’s inbox for you.

Tip #3: Sell the startup sizzle.

An obvious tip but it’s worth emphasizing. Chances are that you are not going to offer the best compensation package when hiring an intern for your startup. So sell them on the experience. After all, one amazing experience on a resume can transform a student’s entire career trajectory coming of college. And there’s no better way to get experience than working in a startup.

So back to my original story: how did I get 40 resumes in one day? Well, I was right in the middle of an accelerator program and I made sure I sold the startup sizzle. “We were selected out of more than 100 nationwide applicants for this accelerator, and this is your chance to be a part of it.” “You’ll have direct access to countless startup CEOs and investors.” “You can help define the end-to-end strategy for an entire company.” You get the picture. It was all 100% true, and it was the kind of experience no other internship was offering.

E-file an 83(b) election

If there is one thing a startup founder needs to know about the tax code, it’s the 83(b) election. An 83(b) election essentially allows a founder to recognize income on the stock at the time it is awarded (which generally means zero income) versus at the time the stock vests (which, if things go well, could be a substantial amount of income). Discussion about the 83(b) election comes up quite frequently in startup circles, and most everyone knows that the election must be made within 30 days of the stock purchase date. That said, people often forget to mention that you also need to include the 83(b) in your annual tax filing. I recently completely my personal tax return with my wife, and was ready to e-file, when I got stuck with the question: How do I e-file an 83(b) election?

Can TurboTax e-file an 83(b) election?

I now have the answer, but first a little background: I used Turbotax Home & Business to fill out our taxes this year and did not see any call outs for the 83(b) election. Given that I have zero income to report from the stock purchase (again, this is the point of the election!) I wasn’t too concerned about missing a number in the income section. Rather, I was nervous about e-filing knowing that the 83(b) election was supposed to be included with my return. I was hoping that there was some way to electronically replace the need to include a copy of the election. Yes, I am that lazy.

In the hopes of having to succumb to the worst option of all — printing out our return and mailing it manually (yuck!) – I took to Google. It was comforting to see the auto-complete fill in “efile 83b election” and a number of results pop up from Intuit’s site. Unfortunately, after reading the top five results, I discovered that nobody had a clear answer. Some answers indicated that it is not possible to e-file your return if you need to include the 83(b). Other people seem to know how to e-file an 83(b) election, but are actually using some super version of TurboTax for real tax professionals (…and those of you who bought TT Premier thought you were badasses). It quickly became clear that neither Intuit’s forums or TurboTax-for-regular-people were going to help me.

Yes, I called the IRS

I had no choice but to call the IRS —  the week that taxes are due. I actually got someone on the line right away, but I made a critical mistake and ended up waiting about 90 minutes for someone who could help me. When I dialed the number, I should have selected “Complex personal tax questions”. I kept asking about how I could e-file an 83(b) election and they kept redirecting me to someone else. It took talking to three representatives before I figured out that I was simply waiting in the wrong queue.

I should say that the folks answering the phones at the IRS were extremely nice and I ultimately did get a clear answer.

How to e-file an 83(b) election

Drumroll tax nerds, here is the solution:

  1. Go ahead and e-file your return like you normally would
  2. Then, snail mail the following to your appropriate tax filing center
    • A cover letter with a explanatory statement (see below)
    • A copy of your 83(b) election
    • A self-addressed, stamped envelope so that the IRS can mail you back confirming receipt

Here is what you need to include in the cover letter, word for word from the agent helping me:

Pursuant to treasury regulations section 1.83-2C per section 83 of the internal revenue code of 1986 as amended, enclosed please find a copy of an election under section 83(b) of the code.

And that’s it. Although this is technically not a way to e-file an 83(b) election itself, it is a way to e-file your entire return while only mailing in two simple documents. I hope this helps!

* Note: I am not a tax professional. Trust me at your own discretion. Better yet, call the IRS 🙂


Entrepreneurs don’t know anything

It takes a fair sized ego to become an entrepreneur. You have to believe that you are capable of accomplishing something that most never dare to try and very few achieve. In many ways, stubborn self-confidence is a necessary personality trait because so much of entrepreneurship is about perseverance. That said, I’ve come to believe in a greater truth: in the grand scheme of things, we as entrepreneurs simply don’t know anything. Yes, we must swallow our egos and admit it. Entrepreneurship is a constant state of learning.

It’s not that we are not skilled in our respective craft (e.g. engineering, marketing, etc) or that we aren’t subject matter experts in our problem domain. Rather, building a business from the ground up involves so many other internal and external factors that it is virtually impossible to have all of the answers from the start. For example, you might be…

…a genius product designer, but…

  • Is what you think is important also important to the customer? How much does the customer even care about the technology itself?
  • What really separates you from competitive solutions? Will your customers see it the same way?
  • Which product capabilities are really nice and interesting, and which ones actually impact your ability to acquire customers?
  • Do you need a user interface to start selling? What about a real backend?
  • What does your customer need in the product despite what they think they want?
  • What key ingredient is missing from your product that nobody is talking about?

…a marketing mastermind, but…

  • What are your key market segments? Which one should you target first? What about next?
  • What marketing channels are relevant to your audience and which ones aren’t?
  • In what ways must you change your approach over time as you increase brand awareness and acquire reference customers?
  • What messaging resonates most with your target audience? If certain messaging is ineffective, how might you tweak it to make it effective?
  • What can you optimize to achieve the most bang for the buck? And when do you move on to the next thing?
  • How can you best impact the sales process? Are there objectives that could be better achieved via marketing rather than direct sales, or vice versa?

… a sales superstar, but…

  • Who is your ideal customer contact? Is that the only person you should be interacting with during the sales process?
  • What is your customer’s overall process for making a purchasing decision?
  • What is your actual sales funnel? Where are sales getting stuck? How, if at all, can you impact the purchasing timeframe?
  • How price sensitive is your customer?  How can you tell that you are pricing correctly? Perhaps price is too high? Or too low (yes, really)?
  • How should you best qualify a lead? Are there non-obvious patterns and characteristics among those that buy?
  • What questions should you be asking your prospects? What do their answers actually tell you?

…a passionate and determined CEO, but…

  • What is the most important thing you should be doing right now? Today? This week? This month? This year?
  • Who and when do you need to hire? How will your hire impact the short term, versus the long term in this business?
  • How applicable is the unique expertise and experience of each team member to the current situation? Are you empowering them correctly while ensuring that they too are continuing to operate in a state of learning?

The reality is that the answer to each of these questions is a function of who you are + what problem you are solving + who you are solving it for + how you are doing it + the current market conditions and timing + … + a host of other other factors. The first step in getting to the truth is admitting that you don’t yet have the answers. This is both humbling as well as empowering. It allows you to stop worrying about who is wrong and who is right; if nobody knows the answer, then trying and learning means that you are making progress towards the end goal. And, ultimately, creating real knowledge — rather than preaching assumptions and beliefs — is a much better way to stroke your ego.


Mixergy Mega Tip: PR without pitching yourself

I absolutely crave hearing the back story of how an entrepreneur built his or her company. For this reason, I am a huge fan of Andrew Warner’s Mixergy. Now that I have a daily 20+ minute commute to our office in Durham, I’ve been trying to catch up on the archive of Mixergy episodes. Not only do I find each founder’s story fascinating, but there is often an “aha moment” or two that really stick out. I thought I would start recording those here as a catalog I can refer to in the future.

I’ve spent a bit of time these past few months reaching out to journalists (mostly cold) and trying to drum up some “free” exposure for the company. I’ve had a couple of hits — including a nice article in InformationWeek, as well as exposure in a few key industry publications — but, by in large, it has been a time consuming and draining effort. That’s why I was really excited to recently listen to Grasshopper’s David Hauser talk about his approach to PR in a Mixergy interview from about 18 months ago.

To me, one of the hardest things about “organic” PR is the concept of building a relationship with a journalist. It sounds simple but how exactly do you do that well? The most obvious thing to do is comment on their articles and try  to engage them on Twitter. But doesn’t everybody do that? And how do you avoid coming off like you are just trying to pitch yourself? In his interview, David mentioned three examples that I thought were instructive.

The Thank You card

In the interview, David talks about how he sent a physical thank you card via snail mail to a journalist they wanted to engage. The thank you card was in response to an article that the journalist wrote, but here’s the kicker: the journalist’s article wasn’t about David or his company. Instead, it was just an article that David genuinely enjoyed reading. Furthermore, in the thank you card, David did not pitch his business or make any sort of ask. He just said thanks, and included a business card.

Pitching the company

Another example he gave was how they would pitch journalists about the culture at Grasshopper. That’s right. Not the product, or even the core mission of the company (at least directly). Instead, they would pitch something like a charity effort that Grasshopper was involved in. Or perhaps how they FedEx’d 5,000 chocolate covered grasshoppers to influential people across America.

Pitching someone else

This was a very subtle point in the interview, but it’s something that really stood out to me. If a journalist is not ready to write about you and your company, you can still help them write about what they are actually interested in. In David’s case, he could connect journalists with other entrepreneurs (i.e. Grasshopper’s customers) to help them fill out their stories. In essence, he made himself a resource to them until they were eventually ready to write about Grasshopper (or perhaps even felt slightly obligated to!).

Although not completely earth shattering, it’s helpful to step back and think of PR in this way. All too often we are eager to pitch ourselves and get exposure as fast as possible. That seems to be the wrong approach. PR is a long game, and it takes patience. Thank-You-card-sent-via snail-mail-kind-of-patience.