21 episodes

For many, it often feels like you're starting over. However, each business endeavor you pursue and every job you take builds new experiences and new skill sets. We will be exploring how to become aware of your collective skillset to be successful moving forward.

Looking Backward Chad Sakonchick

    • Business
    • 4.8 • 26 Ratings

For many, it often feels like you're starting over. However, each business endeavor you pursue and every job you take builds new experiences and new skill sets. We will be exploring how to become aware of your collective skillset to be successful moving forward.

    From Lemonade to $10m in Fitness Products with Paul Jackson

    From Lemonade to $10m in Fitness Products with Paul Jackson

    Paul Jackson from Animalhouse Fitness discusses Monkey Feet, which allows users to lift dumbbells with their feet. He talks about the other products they sell, their team structure, and their approach to outsourcing.



    Paul shares his entrepreneurial journey, starting from selling lemonade as a child to working at an engineering firm and running his own clothing company, The Stoke Company. He highlights the lessons learned from these experiences and how they have influenced his work at Animalhouse Fitness.



    The conversation explores the importance of taking risks, learning from failures, and having the grit to persevere in entrepreneurship. It emphasizes the need to get your reps in, try different business ideas, and learn from each experience. Luck and opportunity play a role in success, but preparation and taking advantage of opportunities are equally important.



    The conversation also touches on the prototyping stage and the value of customer feedback. Starting a business as a side hustle and gradually transitioning to full-time is a common approach. The conversation concludes with a discussion on the challenges of scaling a business and the need to delegate and remove bottlenecks.



    Takeaways

    - Animal House Fitness is a company that sells fitness products, with their main product being Monkey Feet, which allows users to lift dumbbells with their feet.

    - They have a small team and outsource various tasks to agencies, such as email marketing, Google ads, influencer seeding, and bookkeeping.

    - Paul Jackson's entrepreneurial journey started with selling lemonade as a child and progressed to working at an engineering firm and running his own clothing company, The Stoke Company.

    - Lessons learned from previous ventures, such as product design, branding, and social media marketing, have influenced Paul's work at Animal House Fitness.

    - The trend of manufacturing returning to the US is slowly emerging, but there are still challenges such as language barriers and cash flow constraints that make outsourcing to China more viable for many businesses. Take risks and try different business ideas to find success.

    - Learn from failures and use those learnings to improve future ventures.

    - Luck and opportunity are important, but preparation and taking advantage of opportunities are equally crucial.

    - Prototype and gather customer feedback to refine your product or service.

    - Starting a business as a side hustle allows for gradual growth and transition to full-time.

    - Delegating and removing bottlenecks are essential for scaling a business.



    Resources

    ProtolabsXometrySendcutsend LinkedinIG

    • 58 min
    From Busboy to $1M Tax Tech with Max Minsker

    From Busboy to $1M Tax Tech with Max Minsker

    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.

    • 59 min
    From Finance to Steering 1000s of Monthly Fishing Expeditions

    From Finance to Steering 1000s of Monthly Fishing Expeditions

    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.

    • 55 min
    From Playground Hustler to $10m+ Collegiate Apparel Empire

    From Playground Hustler to $10m+ Collegiate Apparel Empire

    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.

    • 1 hr 3 min
    From Pixels to Partings: $3m/year Funeral Home SaaS

    From Pixels to Partings: $3m/year Funeral Home SaaS

    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.

    • 1 hr 13 min
    Ellen Cassidy: Cheese Shop to Million-Dollar LSAT Educator

    Ellen Cassidy: Cheese Shop to Million-Dollar LSAT Educator

    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

    • 55 min

Customer Reviews

4.8 out of 5
26 Ratings

26 Ratings

bikesquad ,

Great interviewer and interesting guests

I was lucky enough to get interviewed by chad. Great guy, great questions, and love all the other episodes of the show. Keep it up!

sibilation ,

Looking Back, Looking Forward

This podcast does a great job of exploring the hills and valleys of entrepreneurship. Chad, the host, is very engaging, and does a great job of drawing out useful information from his guests. I highly recommend this 'cast if you are thinking of starting a business, and want to learn from other peoples failure and successes.

Bryn Bray ,

Very real and honest, a conversation amongst friends

Great podcast that goes through individuals’ life stories of how they got to where they are. Very real and honest, a conversation amongst friends. It’s not always easy but it’s worth it. A great listen for entrepreneurs all over.

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