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I feel the same.

My theory is that I’ve learned from my past mistakes of being a shut-in due to social anxiety, which led me to spiral downward when things inevitably went wrong in life.

I decided to do something about that: face my anxiety head on.

Now I have a thriving network of close friends, colleagues, mentors, and family. Things will go wrong, but I have a support stem. I will be okay.

Being okay is rad.

One of the most surprising parts of this transformation is when people reach out to me after something has gone wrong in their life. I used to freeze in those moments. Unsure how to act or what to say. Now I feel honored to be there for a friend, and it’s rewarding in ways I never thought possible.


Over what timespan did you do this, and do you have any tips for others who should be doing the same thing?


Exposure therapy over years. I don’t think I’m done, so I’d say I’m still at it. But not how you think.

I was fortunate to have a major career change thrust upon me.. it was too good of an opportunity to pass up, so I took it. It required me to go from a passive customer-facing role to an active customer-facing role.

It was difficult, and I struggled early on, but I feel like I’m the type of person who can rise to a challenge. Usually that’s a technical challenge or something less personal, but I just kept tell myself that I was the type of person who can rise to any challenge and kept going.

When this career change presented itself, I had just had my first child, and I wanted to be better for him. I wanted to be a good role model.


Running a server means installing, configuring, and maintaining an OS and stack of software. Spotify running a server in the background isn’t what Moxie means.


I spent a lot of time working on myself, first.

For me, that looked like understanding past trauma, and then doing the work: meditation, journaling, fixing diet and exercise, sleeping better, and enhancing existing relationships with friends and family.

Then, I felt more comfortable knowing myself and being my authentic self. With that foundation in place, I put real energy into expanding my communities. I put myself out there. I asked people to hang out, and I shared my struggles. I was more comfortable being vulnerable.

There are other tactics that have worked. I introduced like-minded people to one another and let those connections grow on their own. I spend time on touching base. When I read an article or see a tweet that a distant friend might enjoy, I send it. And ask how they are doing. I lean into curiosity about others. Ask people probing questions about their lives, hopes, fears.


"When I read an article or see a tweet that a distant friend might enjoy, I send it."

This is also a trick I commonly employ. I rekindle our common interests with things I'm learning or reading and it is serves as a great launch point for discussion when we reconnect. I've affectionately earned a reputation among my friends as a "spammer", but perhaps that is better than "absentee"!


In general communications with your more distant friends have considerably higher Shannon entropy than communications with close friends, for obvious reasons. Which means that often it's a real treat to get messages like that.


I find it funny that the comments here split across:

“I have no doubt that life emerged from an RNA first world”

and

“I have no doubt that life emerged from a metabolism first world”

Last I checked, nobody should have absolute certainty for how life began. Progress comes from skepticism. Have more doubt!


Given the instability of ribose even in plain pH 7 water, and the indiscriminate results of abiotic carbohydrate synthesis processes, I find the RNA-first hypothesis unlikely.

https://www.jstor.org/stable/2368016


I do not doubt things just to doubt them however. Doubt has to be reasonable.


I don’t understand why “pre-made sandwiches” are a common occurrence. Occasionally necessary, sure.

On an average day, if I don’t have 5-10 minutes to wait for a freshly made sandwich, I’ve gone wrong.


My reply is probably too late, but I'll post anyway for people referencing this later.

My own journey over the last 20 years has been a slow migration from a technical contributor (About 10-12 years of systems engineering, infosec consultant, pentester) to a full blown quota-carrying, territory-running sales guy. Surprisingly, I enjoy the work. My personal view of sales started negative based on my interactions with the last generation of salespeople, but I've seen a generational shift in Enterprise Sales recently, and there are a lot more people like me than 10-20 years ago when I started in the industry.

It turns out, sales and running a territory is like engineering to me. Like any good engineer, I enjoy building things. I built out a customer base that can contribute to local chapter events to be where I can't. The job is also highly measureable. I can't think of another role where performance is so easily measured day-to-day and forecasted into the future. It's also a critically important function of the company. Bringing in revenue is a top priority and receives a lot of benefits. One driving force that got me to where I am is that I always took steps of becoming more important.

Back to the question.. how to get good at sales? Easy. Take a sales job. A good place to start would be Sales Engineering or Sales Overlay (SME with sales responsibilities). I'd look for a field that is highly technical and complex. Something hard where real technical chops are required and respected. Customers value your output because they genuinely don't have the expertise that you offer. Nothing commoditized.. look for smaller, fast growing segments.

As for specific skills to succeed in sales in these environments, it's mostly about understanding the customer's business problems and objectives. Once you have a firm understanding and agreement with the customer on the desired business outcomes, then dig deeper into making the individuals at the customer successful. Make your customer a hero. Help them overachieve on their goals. Financial reward comes quickly after you reach this point.

Also important: good communication, systems-thinking (ability to navigate complex organizational decision making processes), and understanding people/empathizing with your customers. Over time you'll develop good instincts to know when to push or when to say no. So much of sales can be subjective, so try to use repeatable processes where possible. Your pricing strategy should be defensible and systematic. Don't make shit up.

To get the above to work for you, you must have strong communication skills. Sales is still about talking to other humans. You get small windows of time with influencers, decision makers, and buyers. You have to have good presentation skills and be able to convey value to a customer with clarity. To distill complex ideas down to simple, meaningful value and tie that to the customer's desired outcomes. The customer needs to be able to answer the question of "why choose these guys instead of those guys?" with confidence and expertise. Most of the real selling happens without you in the room, so you need to build them up to be your champion. When you are in the room, you need them to be your coach.. every meeting should be an open book test. Your coach should tell you in advance who cares about what so you can craft your messaging around things that matter to these decision makers or influencers.

The idea that there is some magical persuasion element in sales seems dated to me. Enterprise sales campaigns are complex. 6-18 month sales cycles with dozens of influencers, decision makers, users, buyers, and so on. You don't take someone out to a steak dinner and close a deal. Does charisma and charm help? Sure.. in a few marginal ways. But you don't have to be a cliche salesperson to be successful. You have to understand how the organization makes a decision, and then work backwards to provide the right information to the right people. Explain the technical value to the people who care about technical aspects. Explain how the license model scales to the person running the budget. Explain how your added services will help the guy in charge of operations scale up the program and over achieve on his goals.

Also, the best sales people pick great products in growing markets. That's where the money is. Mediocre products in stable markets do not attract talented sales people.


Enterprise software sales has changed dramatically in the last 10 years, largely due to the shift to SaaS and the shifting strategy from land big to land fast.

If you look around the younger generation succeeding in enterprise sales, you'll find that many come from a far more technical background. Maybe they transitioned via sales engineering roles first, but the next generation of field sales reps often have real world experience to apply in a consultative sales process.

The days of closing deals over steak dinners or on the golf course are over. Providing real business value in the short term during a quick POC is a must-have. Delivering on real business objectives over the first 6-12 months to ensure the expansion is too.

Some of the old guard, at least the ones that are any good, have adapted. A lot of the old skills are still useful for building relationships and trust. Being able to manage complex organizational challenges that getting more and more complex is an asset as well.


Every strong engineering team needs someone with real security chops.. not just someone who can fix SQLi after it's been pointed out, but someone who gets security at the infrastructure level. Someone who gets the why, not just the how. Not every team has that person or that person can't devote the time to play that role.

With a few good references and strong VC/Accelerator connections, this boutique consulting business should do fine. The question for me is how much pain is there on the board/founder (the key influencers/buyers of the service) compared to the cost of the services... or the risk of doing nothing.


Most startups don't need a dedicated security person and don't need a service like ours to bridge them to a full-time internal security team. So I think you're right: boards and founders are going to question whether they want something like this.

On the flip side: we have the bandwidth for only a few clients (we're doing a lot of work here), so mutual selectivity is a win. :)


I haven't tried Very Old Barton... but I will.

Based on your comments here, we may like some of the same whiskies. I'll add a few to the list:

Four Roses Small Batch 90

Blantons 93

Four Roses Single Barrel 100

If I'm making a large batch cocktail.. I go for Old Overholt. Hard to beat for the price.


The challenge is to provide more value than the alternative. Enterprise SaaS works where it makes sense, and it doesn't where it doesn't.


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