My Career has Been a Process of Trial & Error – Part 4

Click here to read part three of “My Career has Been a Process of Trail and Error”


After business school, I got to work on two development projects — a beautiful 3,000 acre resort project in Napa Valley and a sleek 42-story condominium building on the Dallas skyline. Simultaneously, I was working as the first employee of a startup that my bosses were partners in (one of the benefits of working for a small entrepreneurial firm). Five years in, after the Dallas project finished, and the startup stagnated for a variety of reasons, all of the sudden I found myself in a seemingly perfect situation — I was making good money without much responsibility. I quickly became bored to death. I had no real purpose and I was no longer learning. I realized that being challenged was just as important as making money. I felt the need to take a risk and either start a business or figure out a way to buy one. Going out on my own would expose my weaknesses, but would also give me the opportunity to become a stronger professional. Regardless, just thinking about it made me feel inspired, nervous, and more alive, which I thought was reason enough.

My sister runs a small physical therapy company that her and I contemplated buying on several occasions. We met with the owner a few times, but ultimately decided not to move forward. I had developed a good rapport with him though, and a couple of months later he suggested I reach out to his son, celebrity chef and entrepreneur, Duff Goldman. He was interested in taking on a partner to help manage his businesses. I jumped on a plane to LA for a marathon weekend where he gave me the overview of all his various interests, including TV, appearances, books, license deals, bakeries, and other ventures. We had a common vision for a partnership, felt like we could work well together, and were able to make an agreement fairly quickly. That was two and a half years ago, and so far it has been the best career experience of my life. It checks all my boxes: I’m challenged, I have upside, I’m learning, I have autonomy. I work with an interesting, smart, diverse array of people. I’ve gotten to shape the company and help improve it in tangible ways.

Even though, I am lucky enough to work in a fun industry, it is still work. I hear a lot of people say their dream is to open their own bakery or cake shop. Sometimes I get the impression that people think my job entails sitting around eating and ogling at beautiful cakes. While I do some of that, the other 99% of my time is spent responding to emails and phone calls, sitting in meetings, making to-do lists and spreadsheets; managing investors, employees, lawyers, consultants, and vendors; and dealing with HR problems, legal contracts, insurance, accounting, budgets, and compliance. Most of what I do isn’t very glamorous; in fact, it can be granular, complicated and sometimes boring. Progress doesn’t come easily, but when it does it’s extremely gratifying. I love the process of collaborating with my coworkers to build a better company. Getting on a career path that I’m excited about took a long time, and that’s just the first step. Now, of course, I feel the urgency to make progress.

The most important things I’ve learned about figuring out what to do for a living is that experimentation is key and to put any job in perspective, you need something to compare it to. I would add that beyond thinking about specific functions or roles, it’s worth considering what other variables might be more relevant, like company size, culture, compensation (amount and type), flexibility, stakes (are lives at risk?), status, degree of influence, breadth of responsibility (9 to 5 or 24/7), etc. The list is different for everyone, but the only way to figure out which variables matter most is by exposing yourself to different ones. The best thing I ever did was to get real world exposure to a number of different companies and work environments early on. Not only did it help me figure out what career characteristics would be more likely to make me happy, but it also helped put different positions in perspective. The only way to develop that perspective is through a process of trial and error.

My Career has Been a Process of Trial & Error – Part 3

Click here to read part two of “My Career has Been a Process of Trail and Error”


I learned a lot in that job, including the fact that consulting wasn’t what I wanted to do with my life and that, instead, I wanted to be in a principal role. I wanted to be in position to drive the process, not just advise on it. I wanted to make decisions and live with the results. I switched to a small real estate private equity fund. I was learning, the atmosphere was casual, and the people were smart, but down to earth. There was little to no bureaucracy. I felt at home in a company culture for the first time in my career. Among other things, I learned the importance of fit.

Although it was a great experience, I realized that working directly for the two fund managers, there wasn’t much potential for growth so a couple of years in I applied to business school. I wasn’t sure if I wanted to go, but I also didn’t know what I wanted to do long term, so I thought having an MBA would create options. My world broadened. I met great people. I was reevaluating my career path yet again — career panels, interviews, conversations with classmates, around and around. The truth is, most people in business school don’t know what they want to do for a living, which is exactly why they go to business school to begin with.

I had a great professor in college that emphasized the importance of ownership. That stuck with me. I liked the idea of running a business. Of having more control over my work life, getting to set the priorities, and living with the consequences of my decisions. Living with results has always been more palatable than living with the subjective assessments of other people. I also liked the idea of building something, something that could continue to exist (and I could make money on) even after I was no longer involved with it (the opposite of billing for your time). I also knew I wasn’t an “expert personality”, I would never be able to compete with the quants and engineers. I am much more interested in how the parts fit together, seeing the big picture, and thinking about where to go next and how to get there.

After looking into several different paths, I once again concluded I wanted to be an entrepreneur, but didn’t have any great ideas. So, once again, I decided that the real estate industry would offer the best opportunity for me to continue moving in an entrepreneurial direction as an employee.

My Career has Been a Process of Trial & Error – Part 2

Click here to read part one of “My Career has Been a Process of Trail and Error”


I chose my major through a process of elimination — I knew I didn’t have the science chops to be a doctor. I was interested in psychology, but when I learned there was a required lab that was out of the question. My father complained about aspects of the legal profession, including the hourly billing model. I’ve always preferred subjects that are clearly applicable to the real world, so I naturally gravitated towards business.

I was fortunate to have a several internships in college, the last of which, at Arthur Andersen, landed me a full-time offer in business consulting. My first day of work was September 10, 2001. After 9/11, the economy took a major hit, and the end of that year brought accounting scandals of epic proportions. Arthur Andersen found itself at the center of the imbroglio, and after 89 years in business, the entire company imploded under the weight of a criminal indictment by the Department of Justice (of which it was later exonerated). KPMG acquired the practice I was part of so my coworkers and I were spared layoffs, but that experience taught me to see risk differently. I learned first hand that the idea that bigger companies are less risky is pure fallacy. While working at those firms, I also realized I didn’t want to be on a 20 year pre-determined path, and found all of the layers of bureaucracy to be uninspiring, to say the least. I realized that ending up in a career I wasn’t inspired by was a different type of risk, to my personal happiness.

I was interested in entrepreneurship, but didn’t have any ideas I deemed worthy of pursuing. I looked into different obvious possibilities, like becoming a franchisee, and other less obvious ones that came about, like importing marble from India. I ended up accepting an offer to work at a smaller consulting firm specializing in market analysis for real estate development projects. I was drawn to real estate because it is a highly fragmented industry, which to me meant opportunities for entrepreneurs. It is also tangible, something I desperately wanted after my immersion in forensic healthcare reimbursement audits. The fact that I could actually help create something that people would use was extremely appealing. I also saw it as a good opportunity to experience working at a smaller firm. Maybe consulting wasn’t the problem, maybe firm size was the variable I needed to test.

My Career has Been a Process of Trial & Error

From the time we are young children we are prompted to start thinking about our careers with the age old question — “what do you want to be when you grow up?”.

The suggested answers are always given in the form of specifics occupations — lawyer, doctor, architect, etc. Most of us struggle to figure this out, not just as a kids, but well into our careers. Having wrestled with this question for a long time myself and now finally finding myself in a job I am happy in, I looked back on the path I took to get here.

Over the course of 20 years (including college) and 12 different jobs and internships, I figured out which variables matter most to me in my career — autonomy, ownership, a good culture, the opportunity for growth, a broad scope, and a location that works. I actually don’t care as much about function or industry which are the two variables people tend to think about most.

When I started thinking about this, the first realization I had is that it’s impossible to know you want to do something before you have tried it, so racking your brain to try to figure it out is mostly a waste of time. You have to jump in and correct course along the way. Nothing has helped me figure out what I want to do more than doing things I don’t.

The second realization I had is that since we tend to evaluate most things, including jobs, in relative terms, it’s essential to have a basis for comparison. Just because I love what I do it doesn’t mean it’s always easy, but having worked in a variety of jobs, in different industries, in different types of organizations, I feel like I have a great basis for comparison. That perspective allows me to put my current challenges and frustrations into proper perspective.

As a kid, I had no idea what I wanted to do when I grew up. My career has been a process of experimentation and trial and error, which I think is the only way it can be. That process ultimately landed in a position I am very happy in. As the CEO of a small business, I get to set the direction, make decisions, decide how I spend my time every day, and work with people I enjoy being around. I’m constantly learning and being challenged. I sacrificed compensation to get here, but what I’ve gained in experience is more than worth it.


Stay Tuned for Part 2 of this post, coming soon!

The Value of a Story

I have been thinking about marketing lately and a lot of what I’m hearing and reading points to the central role of storytelling. The idea being that the story of a product is sometimes more important than the features and benefits of the product itself. This reminded me of a couple of entertaining stories I heard about art scams
that illustrate this concept pretty well. Art is an interesting category to think about with respect to the value of storytelling in marketing because the value of the product is highly subjective.

A documentary called Art and Craft tells the story of art forger named Mark Landis who convinced 45 museums all around the world to accept his forgeries into their collections. Landis offered the works for free so he didn’t actually do anything illegal. What’s interesting about this in the context of marketing is that if art can be replicated so well that experts can’t tell the difference between a fake and an original, that seems to confirm that the value of art has relatively little to do with the technical work itself. There must be another source of value in the original that is not present in fakes. I think most people would say the original is uniquely valuable because of its origin, and its history, and that there is only one actual original, so there is scarcity, and that ultimately it’s valuable because the market has deemed it so — all factors that can only be conveyed, or derived, through storytelling. The real and the fake offer the exact same practical utility as a physical good. The only way to know that one is valuable and the other worthless is through an accompanying backstory.

The radio show Snap Judgement ran another story that reinforces this point. A man in New Jersey contrived a tale about a man who kept showing up at his small, unknown gallery in New Jersey leaving behind interesting works of art (one such delivery was handed over in pieces in a garbage bag) but unwilling to reveal his identity. In the gallery owner’s telling, “when [art buyers] heard the story…a firestorm started…the show was an incredible success and a lot of New York collectors were very interested in it.” He goes on to say “once the [New York] Times wrote about it, it was on!” People loved the story. The Times just added credibility to it. Ultimately, the owner came clean and some buyers were understandably infuriated. What’s interesting is the product didn’t change at all. The story he sold them did, thereby diminishing or even altogether eliminating the value of the product in their minds. The value to the buyers was not in the material good, but in its accompanying story and what it meant for them to have a stake in it.

Although neither of these are affirmative examples where true stories added to the value of the product, both illustrate how essential the story is to perceived value, particularly in a category where value is highly subjective. The fascinating thing to me is the same holds true for products with clear utility. I read that the iPhone, for example, is frequently beaten out in terms of features and performance by other competing brands, but people love the Apple story, and as a result, make seemingly irrational decisions in the product’s favor. In most cases, I think both product and story matter. If the iPhone was a terrible product, the story would be irrelevant. The product has to be good, or at least meet expectations. Building trust with customers is essential if you want them to be loyal so telling the truth about the product is also critical. That said, it’s probably important to know when the product is “good enough for now”, and shift resources to crafting and communicating an emotionally compelling story for customers. The reality is most consumers’ physiological needs are finite and generally already being met. Their emotional needs on the other hand are arguably infinite. Those needs aren’t met through features, benefits or facts, they’re met through stories, the stories they tell themselves about what it says about them to buy your product.

For small companies a lack of resources can actually be an advantage

scott dilloff tighten-money

I have worked in several small companies with limited resources. Occasionally, I’ve found myself lamenting that as a problem. Sometimes it is, but when I think about the times we made meaningful progress, pretty much none of them had anything to do with spending money. In fact, it has usually been the opposite – our biggest improvements were born of constraint, urgency, and necessity. Carter Cast and David Schonthal’s Kellogg Voice article “What Corporations Can Learn From Startups” on Forbes.com helped me recognize that being resource constrained might actually be an advantage. When smart people have access to significant resources they, rationally, try to minimize risk by engineering it out upfront. They do this by putting in place process — hiring people, doing market research, and collecting and analyzing data — but that might not be the most effective approach. One issue is that process can create distance between decision makers and customers. When you lack resources, you have to experiment and figure things out quickly. The only way to do that is to take chances to see if something works. A lack of resources also inspires a sense of urgency, which is essential to progress, but hard to fabricate. The article outlines three principles start-ups embrace that can be applied to any company, regardless of size:

  1. “Go Native” – Many big companies rely too heavily on data, and not enough on information gained directly from customers. Engagement with customers in the actual buying environment can yield higher quality information more quickly. My take on this is that getting to know customers is not the same as understanding them on paper. You can’t know someone unless you spend time with them in person in the environment where they are going to decide whether or not to buy your product.
  1. “Embrace Experimentation” – The ethos of the “lean startup” mentality is to figure out the right questions, launch a “minimum viable product”, get market feedback, and use that information to iterate. Too often, larger organizations try to go to market with a finished product. I think part of the reason for this is they are afraid to risk what they already have, namely their brand, but they might actually be creating a bigger risk by going blind. The key might be to figure out ways to hedge brand risk by experimenting under a different banner while applying the same principles.
  1. “Show, Don’t Tell” – Start-ups  “…embody…questions in the form of prototypes.” Again, rather than spend a lot of money trying to answer questions through surveys or other types of secondary research (even asking a customer directly is a form of secondary research), get to market quickly and let the knowledge gained from observing natural, unfiltered reactions dictate the next step.  

For people trying to innovate at large companies, Cast and Schonthal’s article offers some good insights that can be applied from the start-up world. For those of us working at small companies, recognizing that a lack of resources can actually be a competitive advantage is a constructive paradigm shift that helps fuel the inspiration needed to persist through the challenges of early stage ventures.

Scott Dilloff – Volunteering

Why I chose to volunteer with NFTE

I recently volunteered with an organization called Network for Teaching Entrepreneurship (NFTE), a non-profit dedicated to bringing entrepreneurship curriculum into the classroom. The goal is “to prevent dropouts and improve academic performance” among at-risk students by teaching them content they find relevant to the real world. The program uses project-based learning, tasking students with building a business plan from scratch. NFTE essentially treats students as customers, delivering them useful, interesting curriculum, thereby hoping to sell them on the idea that school is worth their while. It is an interesting model and for someone like me, who is pursuing an entrepreneurial career path, it also turns out to be the perfect volunteer opportunity.

The approach

The issues the organization aims to address are dropouts and poor academic performance. The premise being that students make their own decisions about whether they stay in school and how hard they work (which obviously affects performance). NFTE aims to offer content that would increase students’ motivation to do both. There is research that shows it works, and though I am not personally qualified to evaluate it, I definitely buy in.

If NFTE’s premise is right, that we need to “sell” students on staying in school, then the task at-hand is to convince them what they are learning is relevant and they aren’t better off spending those hours doing something else, such as working (a trade-off I imagine at least some low-income students consider).I think we can all relate to the idea that being told we have to do something for a vague or arbitrary reason tends to negatively affect our motivation. The NFTE curriculum helps answer the question all students ask at some point, “why do I need to know this?” It is easy to make the case to students that the NFTE curriculum is worthwhile if for no other reason than it’s about how to make money, which is something we all need.

NFTE’s curriculum focuses on business education, but it has broader applications as well. The main argument I have heard in favor of a liberal arts education is that “it teaches you how to think”. I believe the same is true for the curriculum that NFTE teaches, and it is easier to draw a line from their subject matter to the real world. Developing a business plan from scratch requires students to use their imagination, to think about problems and needs, come up with ideas and solutions, create a plan, develop a budget, and think through logistics, all of which are helpful skills in business and in life. From NFTE’s website: “By teaching the entrepreneurial mindset, NFTE provides young people with tools and attitudes to overcome adversity and address future personal, economic, community and global challenges.”

Consistent with NFTE’s theme of teaching real world content, a key component of the program is to bring volunteers into the classroom to share their experience. This allows students to hear it straight from practitioners, adding further credibility and authenticity to the subject matter. At the end of the course, the students have a chance to compete for seed capital through a series of business plan competitions.

As someone who questioned the value of school on more than one occasion, I think NFTE’s approach of teaching real world curriculum is right on track. In addition to NFTE being a great opportunity to give back for more altruistic reasons, it also offers existing and aspiring entrepreneurs the chance to hone their skills, build their networks, and keep things in perspective.

“While we teach, we learn.”

NFTE’s curriculum aims to increase students’ motivation to stay in school. Similarly, we adults also need motivation to take time away from our busy schedules and spend it volunteering. There are many reasons to volunteer – it feels good, it is a way to meet new people, it can help you develop new skills, to fulfill a sense of civic responsibility, etc. Those are all valid reasons, but I think making the time becomes easier if we do something we are interested in and that ideally aligns with our own goals.

My experience with NFTE involved helping tenth grade students think through various elements of their business plans. I found myself explaining concepts such as market research, market sizing, segmentation, positioning, selling, budgeting, lean operating principles, scale, and so on. It reminded me of two ideas I had heard before, that the best way to learn something is to teach it, and that being able to explain something simply is a true test of how well you understand it. Working with the students on their business plans was good practice, it forced me to organize my thoughts and refresh my understanding of concepts I hadn’t articulated in a while that are relevant to any business, including my own.

On the day I volunteered, I met two entrepreneurs who described reasons similar to my own for getting involved (combination of wanting to give back plus alignment), and I originally found out about NFTE through my friend Jonathan Miller, founder of Element Bars (Shark Tank), GetCheapBooks.com, and other companies. NFTE attracts people who are interested in entrepreneurship, and therefore offers a great opportunity to network with other like-minded entrepreneurial people in your area.

Based on my initial experience, I would highly encourage any business person looking for a volunteer opportunity to consider NFTE. By creating a platform that not only helps students, but also provides compelling reasons for volunteers to get involved, NFTE’s model offers the potential for a virtuous cycle of community engagement, an exciting and motivating idea in its own right.

For more information visit: www.nfte.com

Scott Dilloff is CEO of Charm City Cakes, the business made famous on the Food Network show, “Ace of Cakes”. The brand operates two custom cake studios, a DIY cake-decorating studio (Duff’s Cakemix), and a licensing business with an array of packaged foods and consumer products, including ice cream, boxed cake mix, bakeware and decorating supplies. The products are sold in mass-market retailers nationwide, including Wal-Mart, Target, Michaels, and several grocery chains. He lives in Los Angeles.