Looking Backward

Max Minsker is the founder of Bookmate, a tax filing service for small businesses and startups. Bookmate takes care of everything when it comes to filing taxes and ensures compliance with the IRS.

Chad and Max discuss the differences between traditional CPA firms and online services like Bookmate, highlighting the advantages of specialization and targeted customer segmentation.

Max discusses his early work experiences as a busboy, in door-to-door sales, and in internships at large corporations. Max Minsker started a company called 2K Analytics, which provided analytics and media coverage for the NBA 2K League. He started the company as a side project while working full-time and eventually got the opportunity to consult with the Minnesota Timberwolves, which led to a full-time position with the team.

After working for the Timberwolves for two years, Max set a goal to start as many businesses as needed to be able to live full-time off of them by the time he turned 30. He experimented with various business ideas, including a sports data company and a crowdfunding platform for scientists, before starting a bookkeeping company that eventually took off and evolved into Bookmate.

Max focused on providing affordable and high-quality tax services to small businesses and built a strong customer base through ads, partnerships, and referrals.

Takeaways

- Bookmate is a tax filing service that caters to small businesses, startups, and international founders of US businesses.

- Online CPA firms like Bookmate offer targeted customer segmentation and specialization, allowing them to provide better service to specific types of businesses.

- Working in large corporations can be repetitive and lack the ability to make a significant impact.

- Early work experiences, such as being a busboy and doing door-to-door sales, can provide valuable lessons and insights for future endeavors. Starting a business as a side project while working full-time can lead to unexpected opportunities and success.

- Passion and interest in a specific industry or niche can drive the creation of a successful business.

- Experimenting with different business ideas and being open to pivoting can lead to finding the right business model.

- Focusing on providing affordable and high-quality services in a high-trust industry can lead to customer satisfaction and referrals.

Captain Experiences is a platform for booking outdoor sports guides, starting with hunting and fishing. They have partnered with 1500 guides and have become the largest platform in the U.S. for booking fishing trips. They have about 200,000 monthly site visitors and are steadily growing.

Jonathan, the founder, didn't have early entrepreneurial experience but had a background in bartending and finance. The customer service skills from bartending and the modeling and Excel skills from finance have influenced his approach to running Captain Experiences. They prioritize customer satisfaction and have implemented processes to ensure accurate trip listings and address any issues that arise.

Captain Experiences started by focusing on solving the cold start problem by first building the supply side of the marketplace. They reached out to fishing guides and offered to take care of all the heavy lifting for them, including managing their calendars and creating their profiles and trip listings. This approach allowed them to onboard guides and build liquidity in Galveston, Texas. They then expanded geographically, focusing on markets where they needed more guides and where there was potential for growth.

They used SEO and events to fill the gaps in the early days and later implemented programmatic SEO to scale their growth. They also leveraged word-of-mouth referrals from existing guides to attract new guides to the platform. Captain Experiences plans to expand into other outdoor sports and geographies, with the goal of becoming a global business.

Takeaways

• Captain Experiences is the largest platform in the U.S. for booking fishing trips
• They prioritize customer satisfaction and have implemented processes to address any issues that arise
• Jonathan's background in bartending and finance has influenced his approach to running the business
• They earn a commission on every executed trip Captain Experiences focused on solving the cold start problem by first building the supply side of the marketplace.
• They onboarded fishing guides by offering to take care of all the heavy lifting for them.
• They used SEO and events to fill the gaps in the early days and later implemented programmatic SEO to scale their growth.
• Word-of-mouth referrals from existing guides played a significant role in attracting new guides to the platform.
• Captain Experiences plans to expand into other outdoor sports and geographies, with the goal of becoming a global business.

Nesha Sanghavi, founder of chicka-d, discusses the brand's focus on elevated premium essentials for women, with a primary market in collegiate apparel and secondary resort market selling non-licensed items to vacationers.

The majority of chicka-d's business is wholesale, with a small percentage in direct-to-consumer (DTC) sales. Nesha shares the inventory and payment process for wholesale orders, as well as the company's growth from a small team to 40 employees.

She also reflects on her early entrepreneurial experiences selling hair clips and working at a pool concession stand and Limited Too. Nesha discusses her switch from pre-med to finance and her internship experiences at Morgan Stanley and WVBIT.

The conversation covers topics such as unclaimed property, office politics, setting ambitious goals, and the challenges of working at well-known brands. Nesha also discusses her experience at BNY Mellon and Puma, as well as the process of launching her first product line. Throughout the conversation, she emphasizes the importance of being persistent, adaptable, and focused on profitability.

Takeaways

• chicka-d is a women's apparel wholesale brand that focuses on elevated premium essentials, primarily in the collegiate apparel market.
• The resort market is another segment of chicka-d's business, where they sell non-licensed items to vacationers.
• The majority of chicka-d's business is wholesale, with a small percentage in direct-to-consumer (DTC) sales.
• Nesha Sanghavi shares her early entrepreneurial experiences selling hair clips and working at a pool concession stand and Limited Too. Unclaimed property can take various forms, including real estate, safety deposit boxes, and inheritance.
• Office politics and the Peter Principle can hinder career growth and success.
• Setting ambitious goals and believing in oneself are crucial for personal and professional growth.
• Starting a business requires persistence, adaptability, and a focus on profitability.

Will Chang from Parting Pro discusses the challenges of the funeral home industry and how his company is bringing modern tools to an antiquated industry.

He shares his background in computer graphics and his experience working in China. Will also talks about his time at Fundly and his obsession with Y Combinator content. Will Chang shares his journey from working at Fundly to starting Parting Pro, a SaaS platform for funeral homes.

He discusses the challenges and lessons learned along the way, including the importance of evaluating startups based on their actual performance rather than brand names.

Will explains how Parting Pro evolved from a marketplace model to a SaaS product, focusing on the needs of funeral homes and offering services such as e-commerce, website development, and SEO.

He also highlights the role of accelerators in shaping the company's growth and the future potential of AI in the funeral industry.

Takeaways

• The funeral home industry is antiquated and in need of modernization.
• Parting Pro is bringing modern tools and technology to the funeral home industry, streamlining processes and improving the customer experience.
• Will Chang's background in computer graphics and animation has influenced his approach to product development and user experience.
• Working in China provided valuable insights into the startup ecosystem and the challenges of doing business in a different culture. Evaluate startups based on their actual performance rather than brand names.
• Understand the pain points of your target customers and build a product that addresses those needs.
• Consider pivoting your business model to better serve your customers and achieve profitability.
• Building relationships and seeking support from investors and accelerators can be crucial for startup success.

Chad and Ellen discuss her journey towards Elemental Prep, which started as an LSAT prep company but is evolving into an educational course on how to read and think better. Ellen shares her experiences working in various jobs, including cashier, cheese shop employee, and writing tutor. She also talks about her involvement in the tolerance forum and her transition to teaching LSAT with PowerScore. The conversation concludes with a discussion about the Living Flashcards method and the use of ChatGPT in education.

Takeaways

• Elemental Prep started as an LSAT prep company but expanded to become an educational course on reading and thinking better.
• Ellen Cassidy had diverse work experiences, including working as a cashier, cheese shop employee, and writing tutor.
• She was involved in the tolerance forum, where she educated people on LGBTQ issues.
• Ellen transitioned to teaching LSAT with PowerScore and developed the Living Flashcards method to help more students.

Chapters

00:00 Introduction to Elemental Prep

02:28 LSAT Prep as an Educational Course

03:23 The Success of 'The Loophole'

05:33 Creating Elemental Prep

08:35 The Living Flashcards Method

12:16 The Role of Chat GPT

12:54 Ellen Cassidy as an Interactive Miss Rachel

13:23 Early Experiences: Cashier and Cheese Shop

14:35 Cheese Cotillion and Early Education

15:25 PA Governor's School and Writing Tutoring

19:21 Expulsion from Tolerance Forum

20:49 Transition to Palantir

21:36 Working at Palantir

24:04 Writing Tutoring and Camps

24:28 Office Work at Rutgers Theater Department

25:19 Interest in Theater and Writing

26:53 Transition to Elemental Prep

28:10 The Hot Tub Party

29:17 From Palantir to Bricks and Mortar

30:01 The Power Score LSAT Teaching

Will Tjernlund of Goat Consulting discusses how his company helps brands and manufacturers sell more effectively on Amazon. They assist with catalog organization, choosing the right business model, logistics, copywriting, marketing, and day-to-day case management. Many of their clients are new to B2C and are transitioning from selling to other businesses. Will explains the process of cleaning up existing Amazon listings and using Amazon's Brand Registry to override incorrect information.

He also shares his background, including working at Target, running a casino in high school, and his time at Tjernlund Products before starting Goat Consulting. Will Tjernlund shares his journey of starting the FBA Mastermind, selling it to Empire Flippers, and then starting Goat Consulting. He discusses the challenges and successes he experienced along the way, including transitioning to an agency model and determining pricing. Will also talks about the importance of creating a website and blog posts to attract clients and the future of Goat Consulting.

Takeaways

• Goat Consulting helps brands and manufacturers sell more effectively on Amazon by providing a range of services, including catalog organization, logistics, copywriting, marketing, and case management.
• Many clients are transitioning from selling to other businesses and are new to the B2C space.
• Cleaning up existing Amazon listings is an important part of the process, and Amazon's Brand Registry allows brands to override incorrect information.
• Will Tjernlund's background includes working at Target, running a casino in high school, and working at Tjernlund Products before starting Goat Consulting. Starting a successful online business can lead to unexpected opportunities, such as selling the business to a larger company.
• Transitioning from a solo entrepreneur to an agency model can provide stability and scalability.
• Creating a website and writing blog posts can be an effective way to attract clients and establish expertise in a specific industry.
• Determining pricing can be a challenge, but offering a flat monthly retainer can provide stability and predictable income.

Exploring many different opportunities is a great way to gain a broad range of experiences while narrowing down what craft you want to pursue. Travis Devitt engaged in a plethora of different entry level jobs, leveling up each time until he attended a presentation that pushed him into his core discipline of investments. Now marrying education with his domain expertise, Travis is helping others understand the 101s of investing.

Some people love the process of building a business. Figuring out how the puzzle pieces fit together at every stage is part of the fun. But those individuals don't always find immediate success, instead they serially start at the beginning until something hits, which can be years in the making. William Griggs, after years of gaining a broad range of experiences, found a gap in the events market renting expensive technical virtual reality experiences.

What makes you select an item off the shelf in your local grocery store? Pretty packaging, the name, or just a feeling? Social media companies like Facebook have become behemoths because they can sell ads on a very granular level to marketers. Alison Smith at Umai Marketing does just that for Consumer Packaged Goods (CPG). Having bounced around from the family pump business, to LA fashion, and drop shipping in Vietnam; she now helps you make the decision on which eggs or coffee to pull off the shelf long before you step into the store.

Entrepreneurship is serendipity. Chance happens and if you're paying attention, it can turn into opportunity to realize that 5 hour/week lifestyle. It doesn't happen overnight, but if you're willing to put in some hard work up front and sacrifice "safe bets," then you can be like Nick from Storage Squad. One phone call changed Nick's career trajectory from a safe $70k a year job to sweat through moving boxes in the summer heat. Five years later, Nick is helping others realize this same dream through sweatystartup.com

How do people know that your business exists? How do you spend money to educate the right people and avoid wasting money advertising to the wrong ones? Michael Gaman from Gudnow Media specializes in a special intent based marketing known as Search Engine Marketing (SEM). If you've ever searched on Google, you're interacting with the type of ads that he delivers. Michael and I discuss his background while attempting to explain the basics of this technical and complex type of digital marketing.

Not everyone pines after becoming an entrepreneur since they were young. Sometimes, opportunity is sitting right in front of your years of specialized experience and it makes too much sense not to take the leap. Austin Venue Collective is an outsourced service whose customers are the very bars and restaurants you reach out to when you want a private corner for a birthday or the entire venue for an engagement party. Allison's years of experience managing half a dozen venues prepped her for this next part of her accidental journey.

How do you think your electricity bill is calculated every month? Turns out there is a very complex system of buying and selling that goes on. Matthew Boyda stumbled onto a public data file while working on a related project, allowing him to start Energytics which provides market forecasts for power consumption across Texas.

Ever witness a great restaurant that opens a second location then goes downhill? Harlan discusses how an early experience at a corporate restaurant taught him how to avoid this folly and to run a business instead of owning a job. Having managed half a dozen successful concepts at once, Harlan has had his own issues automating himself out of a job until he decided it was time to launch his own concept.

What business is more common than a food service business? Out of all the types of services out there, the individuals that serve our food and drink are a special set. Cody Taylor started in the food service industry as a bartender, then a server, assistant manager, general manager, and now the owner of two fledgling restaurants. But during the 2008 recession, success meant staying open when no one was eating out. Follow along as Cody learns what it takes to compete in an aggressive foodie market like Austin.

You don't always have to be doing your own thing to be an entrepreneur. Part of the journey is learning from as many sources as you can then picking and choosing the lessons that you deem most important. Current Facebook Programmer Hunter Monk is 26, but has a decade of experience running various businesses. He has hired contractors overseas, managed over $1M in yearly advertising spend, grossed over $1M in annual revenue, and earned investment from Mark Cuban.

It me! So who am I and why am I qualified to have a podcast about turning your failures into a growing skill set? Hopefully this episode will give you a solid background on my 22 years of  work experience. From my first job staring at satellite maps for 8 hours a day to my current venture BetterLegal, I go through the raw details.

Toni has spent the last 12 years taking Jacaruso Enterprises from a small Hilton contractor to a $15M a year business. Listen how she started her path towards hospitality CEO from humble beginnings as a babysitter then working the night shift at a hotel while still in high school.

Looking Backward will be about taking your life experiences into an official skillset that you can be aware of moving forward.