Working Without Pants - Creative Entrepreneurship

Dan Englander is the founder of, and the author of Mastering Account Management and The B2B Sales Blueprint.

Dan is an expert on growing sales, and specifically, getting the most value out of existing clients, which is often ignored in sales.

We dive into his experiences in ramping up sales at one of the first video explainer companies and winning massive Fortune 500 accounts (like Verizon, Showtime, Bank of America, Venmo), before he started his own consultancy.

Highlights of this episode:

[1:44] In the blistering New York summer, Dan wears shorts to work from home, and will often stroll over to a coffee shop- it gets him in a different mindset and is helpful for separating tasks.

[2:20] Before he was the braggadocious founder of, Dan knew nothing about sales. As the first employee of Idea Rocket, he learned sales and made it work.

[3:50] His initial sales process was not cutting it.

[4:20] Things started to turn around. PPC and PR was effective, but winning the show opening for the Showtime Series Weeds help establish them as an authority.

[4:50] Fortune 500 companies find vendors the same way startups do. They won those initial big accounts by becoming a safe bet.

[5:45] The initial big wins gave them validation, and created a snowball effect.

[5:55] The main challenge for their first big sales was convincing them that something so unorthodox (at the time) as investing five figures in cartoon was a safe investment.

[8:15] As the market grew, the game changed from “buy a car not a horse” to “buy a Mercedes not a Honda.”

[8:55] Eventually, they got to a point (which most agencies get to) where the struggle was qualifying and prioritizing.

[9:35] How Dan goes about qualifying and prioritizing for better clients.

[11:18] Dan’s got different arrows in the quiver, that is 2 or 3 different sales processes for the different levels of clients.

[13:10] Establish immediate value by giving prospects a taste of what it’s like to worth with you.

[13:40] The biggest stopping point for many creative agencies is prep work. In order to overcome this, they would offer scripts to their videos, to get in the door and prepare the client.

[15:55] Account management is basically a role that combines client services and sales.

[17:04] Selling to existing customers should be easier than selling to new people, but its potential goes untapped, because most go about it the wrong, awkward way.

[18:25] Start with a partnership mindset. Don’t just randomly hit them up for new business. Build the next steps into your initial process. Be relevant. Find ways to help.

[20:00] Jake has found that quarterly reviews are a great way to reconnect and gauge the impact your work has had.

[20:55] Don’t send donuts.

[21:15] Partnerships are a long game- there’s more ways to pull value from an account than just selling the same product again.

[22:25] Dan discusses his approach to getting referrals from clients.

[24:10] What to look for in hiring a salesperson / account manager: if they could write well, they’re halfway there.

[25:34] Asking the right questions is the most important part of sales. Subject matter expertise is overrated.

[26:44] Aaron Ross stands out as useful to any company trying to implement a sales process.

[27:23] Neil Rackham was ahead of his time.

[28:55] While many young entrepreneurs want a step-by-step guide to succeeding, it’s more about the mindsets that enable success.

[29:35] Dan’s first book is the Chicken Soup for the Soul of account management. Check out the link below for a free copy.

[30:42] By the hard questions early on, you will save time and find more opportunities.


Resources from this episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

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Direct download: WWP_-_Dan_Englander.mp3
Category:general -- posted at: 10:19am EDT

Ben Lee is the founder and CEO of Neon Roots, an award-winning agile development agency.

Interestingly, the majority Neon Roots’ revenue does not come from actual developing, but rather from their discovery program, called Rootstrap, which guides entrepreneurs from the vaguest idea of an app, to a development-ready prototype.

Ben dives into how Rootstrap took on a life of it’s own, why discovery is so important, his untraditional sales team and other insights into how he’s built his business.

Highlights of this episode:

[2:20] Ben has to wear pants at work now, but he did work with Snoop Dogg’s management company before moving to his new location in West Hollywood, and he talks about random run-ins with celebrities

[4:55] He and his co-founder started Neon Roots to challenge the traditional agency model, and actually practice what is preached about agile methods, lean startup, etc.

[6:00] He discusses the bloated, risk-avoidant and unhappy lifestyle common in the service industry, and how he ditched it to start something new- pioneering AR/VR before the market was ready

[7:15] Story carding and discovery was a way to qualify clients, manage expectations, and truly aligned interests- and was incredibly successful

[10:27] How the Rootstrap offer evolved, and how it was influenced by Ben’s background in hospitality

[13:50] He discusses the psychology that goes into the Rootstrap customer experience

[16:00] The Rootstrap Swag Box is a powerful component of the whole experience, triggering positive emotions, and taking on a life of its own as a storytelling mechanism- whether it’s for a 23 year-old first time entrepreneur or Tony Robbins

[19:10] Competitors talk about the Swag Box

[19:37] Discovery and other engagement activities after kickoff are all about providing value to the customer

[21:45] Rootstrap has built a reputation among VCs, from whom they get a lot of deal flow

[22:13] Brand grows in thought-leadership

[23:30] He doesn’t hire sales people, but many former participants sell for him by simply sharing their stories

[25:10] Offering free advice over the phone for young entrepreneurs who aren’t yet a good fit is great for building relationships, which have resulted in referrals several years later

[29:20] Embarrassing sleazy sales guy vs the former participants who aren’t sure their confident enough for sales

[30:39] The sales cycle involves less commitment, or going on dates before you get engaged

[32:35] They (over)deliver so much value that other agencies resell Rootstrap

[33:05] Rootstrap vs ongoing consulting, and why many Rootstrap participants don’t convert because they don’t have an internal dev team or they need help fundraising

[35:18] The solution to a hybrid agency is proper siloing. Going forward, Neon Roots will be doing more creative stuff, which can happen because the service side is completely separate- plus Rootstrap Studios in Uruguay

[40:40] Ben gives his words of wisdom to agency owners to build their way up and increase sales

[42:25] You can reformulate lean/agile methods to any industry/business


Mentioned in this episode:

Direct download: WWP_-_Ben_Lee.mp3
Category:agency owner -- posted at: 11:39am EDT