Do Small Business Like a Big Boss Podcast

Your ideas deserve a home that's yours. Jessica Dalka shares how she turned a side blog into Chicago Planner Magazine, and how she decides what gets her time, her energy and her yes.

Jessica Dalka is the owner and founder of Chicago Planner Magazine, a no-fluff resource for the events and hospitality industry in Chicago. She started it while working in restaurants and hotels, and has kept it going through a pandemic and several big-name event jobs. Host Aisha Jorge Massengill talks with her about starting a business before you feel ready, wearing every hat, and building your own thing alongside a full-time job. You'll also hear how Jessica picks networking events, why she keeps meetings to 15 minutes, and why asking for a fair price doesn't make you a bad person.

💡 What You'll Learn

• How to decide which networking events are worth your time: look at the audience, step outside your own industry, and know when a room is repetitive

• How to keep meetings to 15 minutes by pre-qualifying every request first

• Why testing one small piece before you scale beats a big launch, and what a clean-water project teaches about it

• How to spot early when someone never planned to pay you, and say no without guilt

• Why Jessica adds "accomplishment" alongside "success" when she defines her own impact

⏱️ Episode Timestamps

00:00 – Welcome and meet Jessica Dalka, founder of Chicago Planner Magazine

01:50 – How a steakhouse job and a side blog sparked a business of her own

04:00 – Dream killers, other people's fears and ideas taken without credit

07:15 – Building on the side: focus, sleep and the pandemic networking push

09:15 – Choosing which networking events are worth your time

13:30 – Her writing process: notebooks, compartmentalizing and protecting focus

17:15 – The six-week job that made the decision for her

20:10 – The hardest hat to wear: explaining digital before it was mainstream

21:30 – Digital vs. print: why the mix matters

23:15 – Test one small piece first: lessons from a clean-water project

27:45 – Money and vision: how the pandemic taught her to say no

31:00 – Being of service while respecting what your work is worth

32:56 – Big-business habits: speaking every industry's language and turning creativity into dollar value

35:20 – Making every minute count: pre-qualified 15-minute meetings

39:30 – Tools and routines: "if it's not on my calendar, it doesn't exist"

41:30 – What "enough" looks like and why events are undervalued

43:15 – Advice for the messy, scared first year

44:36 – What "Do Small Business Like a Big Boss" means: being self-defining

🎤 About Our Guest

Jessica Dalka is the owner and founder of Chicago Planner Magazine. With a background in advertising and PR, she has built a career designing events for Fortune 500 executives, celebrities, athletes and politicians.

🔗 Connect with Jessica

Website: chicagoplannermagazine.com

Instagram: @chicagoplannermag

LinkedIn: Jessica Dalka

👉 Stay Connected with Sedgwick Andrews

https://linktr.ee/Sedgwick_Andrews_LC

www.smallbizzlegalguide.com

🎙️ Build the dream messy, build it scared, just don't build it small.

🎧 If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

Tired of marketers who overpromise? Pete Kleinjan, founder of Tiger29, explains why he tells clients to fire him if they're not getting results, and why that honesty keeps them around.

Pete Kleinjan started in SEO in 2003 after his boss handed him a Wikipedia article, and founded Tiger29 in Sioux Falls, South Dakota in 2009. Today the agency serves local service businesses across more than 20 states. In this episode he shares the sales tax letter that made his hands shake, why he waited seven years to make his first hire, how he turned "recipes" into SOPs, the $150 SEO Power Hour that proves value before anyone signs, and why he has worked with one client for 16 years without ever meeting in person.

💡 What You'll Learn

- Why owning a job and owning a business are not the same thing, and how Pete found the difference

- How to set client expectations so honesty wins you referrals instead of costing you sales

- Why "every molehill feels like a mountain until you've climbed it," and what that meant for his first hire

- How to turn what's in your head into SOPs your team can run without you

- Why the systems that get you to $500K a year break at $1M

⏱️ Episode Timestamps

00:00 – Cold open

00:47 – Meet Pete Kleinjan, founder of Tiger29

02:04 – The origin story: a sales guy and one Wikipedia article

02:58 – Why he left a good job in 2009: something better, not more

03:27 – What SEO is, and what AI changed

05:41 – Why the company is named Tiger29

07:28 – Owning a job vs. owning a business

09:07 – The coach, the book and the mindset shift

11:02 – Doubt, resilience and just another Tuesday

12:09 – The sales tax letter that made his hands shake

14:28 – Quick pause: like, follow and subscribe

14:56 – Seven years solo, then the first hire

18:05 – Why he waited so long to hire: fear

19:54 – SEO's bad reputation and the $150 SEO Power Hour

21:15 – Proof over promises: if you're not getting results, fire us

23:48 – Did honesty ever cost him a sale?

25:12 – Handling the no

28:05 – Systems: SOPs as recipes anyone can follow

31:38 – What gets you to $500K breaks at $1M

31:53 – The lottery-ticket file rule

33:55 – Letting go of email: it's handled

35:09 – Quick beat: your free Legal Risk Assessment

35:41 – From Sioux Falls to 20+ states

38:08 – Keeping up with the algorithms: masterminds, newsletters, NotebookLM

41:00 – The gem: surround yourself with good people

42:30 – What Do Small Business Like a Big Boss means to Pete

43:07 – Close: build the dream messy

🎤 About Our Guest

Pete Kleinjan is the founder of Tiger29, an SEO and digital marketing agency in Sioux Falls, South Dakota, that helps local service businesses compete online. He has worked in search engine optimization since 2003, founded Tiger29 in 2009, and is known for the SEO Power Hour, a live session where he makes visible improvements to a business's online presence before any contract is signed. Outside of work he serves as a church deacon and nonprofit board member in the Sioux Falls community.

Connect with Pete: https://www.tiger29.com

👉 Stay Connected with Sedgwick Andrews: https://linktr.ee/Sedgwick_Andrews_LC

https://smallbizzlegalguide.com

https://TopBillingTrademarks.com

🎙️ Build the dream messy, build it scared, just don't build it small.

If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

Learn how to find a brand voice that sounds like you, and how to ride the ups and downs of business ownership without panic.

Becky Freemal spent 25 years as an Emmy Award-winning broadcast journalist before launching Market Exec, a fractional CMO firm that helps founders and leadership teams turn their brand voice into measurable growth. Four years in, she shares what the first scary stretch felt like, where she chose to invest early, and why slow seasons no longer mean "the year of ramen." You'll also hear her simple brand voice test, how to use your own social media data to find your audience, and how she approaches sales calls without feeling salesy.

💡 WHAT YOU'LL LEARN

• How to ride the entrepreneur roller coaster, from "the year of ramen" to a slow summer that included a trip out west

• Where Becky invested early (writing her book and joining a fractional CMO accelerator) and how she judged the return

• A three-part brand voice test: simple, genuine and consistent

• How to find your audience in the data on who already follows you on social media

• A money habit for tax time: keep a separate account for taxes

• How to sell without feeling salesy by leading with your purpose

⏱️ EPISODE TIMESTAMPS

00:00 – Meet Becky Freemal, Emmy-winning journalist turned fractional CMO

02:10 – Why Becky left a 25-year broadcast journalism career

04:01 – Fear, excitement and leaving a safe job

05:02 – The entrepreneur roller coaster: from the year of ramen to a trip out west

08:37 – First months of Market Exec: systems and smart investing

13:54 – Building credibility when you change careers

18:45 – Do you have to prove you belong? Fake the confidence

23:04 – The hardest part: taxes, risk and never letting one person define you

27:09 – Green and growing: why lifelong learning matters

27:47 – A brand habit for solo founders: lead with your purpose

30:36 – How to find your brand voice: simple, genuine, consistent

34:39 – Protecting your time: morning yoga and meditation

37:12 – What Do Small Business Like a Big Boss means: don't play small

38:14 – Final advice: who are you doing all of this for?

🎤 ABOUT OUR GUEST

Becky Freemal is an Emmy Award-winning broadcast journalist with 25 years in news, the founder of Market Exec, a fractional CMO firm, and the author of Brand Voice: People plus Data Drive Results. She also teaches as an adjunct at Virginia Tech.

Connect with Becky:
beckyfreemal.com
linkedin.com/in/beckyfreemal

👉 Stay connected with Sedgwick Andrews: https://linktr.ee/Sedgwick_Andrews_LC
https://smallbizzlegalguide.com
https://TopBillingTrademarks.com

🎙️ Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Nicole Blake Baxter, founder of The Blake Agency, to discuss how small businesses can use public relations (PR) to build visibility, credibility, and stronger audience connections.

With over 20 years of experience, Nicole shares how to create an effective PR strategy without a big budget, why local media coverage matters, and how entrepreneurs can build their digital presence.

🎧 What You’ll Learn:

• The difference between PR and marketing
• Why local media coverage can be valuable
• How to approach sales through storytelling
• How to pitch articles to trade publications
• How earned, paid, and owned media work together
• How to start building your PR strategy

⏱️ Episode Timestamps:
00:43 – Introducing Nicole Blake Baxter
00:46 – PR vs. marketing
03:00 – Her music industry experience
07:29 – Starting her own agency
13:48 – Business partnerships and exit plans
18:50 – Landing her first clients
20:07 – Storytelling and sales
26:52 – Why she turns down short-term campaigns
28:31 – Local press vs. Forbes
33:01 – Building your digital footprint
34:47 – Pitching trade publications
39:50 – Getting started with PR
40:42 – Earned, paid, and owned media
44:50 – Finding The Blake Agency

👤 About the Guest:
Nicole Blake Baxter is the founder and managing director of The Blake Agency, an Atlanta-based public relations firm serving clients nationwide. She has over 20 years of PR experience, beginning her career at Island Def Jam before launching her own agency.

🚀 Make Your Business Official!
Join Aisha’s FREE weekly webinar to learn how to build, brand, and strengthen your business.

👉 Register: https://www.igotnext.co/training

👉 Get Your FREE Legal Guide:
https://smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

If you enjoyed this episode, subscribe, download, and share it with another business owner! 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Marcus Smith, CEO of Cloud Trailz, a Salesforce support, management, and strategy firm, to talk about the systems and strategies that helped him build and grow a successful business.

This conversation covers the real-life lessons behind building a subscription-based business, protecting your company from overreliance on a single referral channel, creating owned content and SEO strategies, and the $300,000 mistake that taught Marcus a powerful lesson: you cannot buy trust from strangers.

🎧 What You’ll Learn in This Episode:

• Why a subscription model can create more stability than relying on one-off projects
• How to protect your business from depending on a single referral or acquisition channel
• Why owning your content and search traffic can create long-term growth
• How “Demo Week” helps improve the quality and speed of your team's work
• The $300K lesson on why trust cannot be bought from strangers

⏱️ Episode Timestamps:

• 00:19 – Introduction
• 00:59 – Guest introduction: Marcus Smith & Cloud Trailz
• 01:54 – Why he built the business on subscriptions, not projects
• 04:00 – How COVID fueled early growth and the risk that came with it
• 08:05 – Insulating the business from a single dominant channel
• 08:48 – Why they invest in owned content instead of renting attention
• 09:16 – SEO explained simply: matching intent to content
• 11:12 – The 3% buying vs. 95% browsing framework
• 12:29 – The corporate moment that made him want out
• 15:11 – How a joke turned him into a CEO
• 16:30 – Handling pushback on the subscription model
• 19:53 – The early hurdle: realizing nobody cares about your new business
• 22:34 – How to actually get customers to care
• 24:48 – A client transformation he's most proud of
• 29:11 – The “Demo Week” structure that changed everything
• 35:23 – The $300K mistake: trying to buy back demand
• 37:49 – Why “systems beat heroics”
• 40:23 – What “Do Small Business Like a Big Boss” means to Marcus
• 41:28 – Where to connect with Cloud Trailz

👤 About the Guest:
Marcus Smith is the CEO of Cloud Trailz, a Salesforce support, management, and strategy firm headquartered in Atlanta, Georgia. The company has helped more than 250 businesses put Salesforce to work for their teams.

Website: https://www.cloudtrailz.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Dan Hafner, founder of Dapper No Code, to talk about building a successful software business without learning to code or hiring a traditional development team.

Dan shares his journey from farm kid to software founder, how he discovered the power of no-code tools, and the mindset shifts that helped him turn his skills into a profitable business. He also explains why he intentionally downsized his team, how AI helps him run a high-output firm, and what first-time founders really need to build a business.

🎧 What You’ll Learn in This Episode:

How to turn an app idea into a sellable product using no-code tools
Why knowing your financial “bottom number” matters before going full-time
The three things every business needs: a way to sell, get paid, and reach people
Why growing a team isn't always the goal and how AI can help you stay lean
How to audit your tech stack and eliminate unnecessary subscriptions

⏱️ Episode Timestamps:

00:39 – Introduction & Guest Introduction: Dan Hafner
01:02 – From farm kid to software founder
02:52 – Dan's first job and early career lessons
04:44 – Landing a QA role at Deloitte
08:07 – Discovering his passion for computer work
11:59 – Deciding to become a business owner
14:16 – Discovering no-code app builders
16:50 – Making the business official
19:07 – The moment it became a real business
20:30 – Quitting his job for good
23:29 – Advice for entrepreneurs afraid of the timing
27:24 – Pricing, confidence, and knowing your worth
29:14 – Growing a team to seven and shrinking back to one
32:02 – AI and no-code tools transforming the business
41:11 – Auditing your tech stack
46:06 – What “Do Small Business Like a Big Boss” means to Dan
47:31 – Where to find Dan and The No Code Advantage podcast

👤 About the Guest:

Dan Hafner is the founder of Dapper No Code, a Pittsburgh-based no-code app and software development firm that helps coaches, experts, and small business owners turn software ideas into revenue-generating products without traditional development costs.

Dapper No Code was recognized as Best of No-Code Development in the USA for 2025. Dan also hosts The No Code Advantage podcast.

Connect with Dan:

Website: https://www.dappernocode.com

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:

https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

Thinking about turning your side project into a nonprofit or small business? Ian Kimble breaks down exactly what to lock in early — starting with the two moves most founders put off too long.

Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia nonprofit expanding access to tech education, digital literacy, and AI literacy. What started as a conversation with a stranger coding in a coffee shop back in 2019 is now a program running in four Philadelphia schools, hosting city-wide Tech Town Halls, and building a growing community of tech professionals and aspiring entrepreneurs. Aisha and Ian talk through the free legal resources that helped him formalize the organization, the importance of building the right kind of culture that shaped how his team hires and holds people accountable, and how storytelling — not advertising — became his biggest lead source.

💡 What You'll Learn

• How to find free legal help for 501(c)(3) formation through pro bono lawyer programs like Philly VIP
• Why culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard early
• How showing up in person and telling one specific, sticky story about your business turns into inbound leads

• How to balance a full-time job with building your business in the early days without burning out

⏱️ Episode Timestamps

00:02 – Welcome & meet Ian Kimble

00:55 – The coffee shop conversation that started Black Tech Philly

02:20 – What Black Tech Philly does today

05:20 – Is the appetite really there for tech & AI literacy?

09:39 – Deepfakes, media literacy, and “trust but verify”

12:23 – Getting free legal help early through Philly VIP

16:03 – The real definition of company culture

19:39 – How a LinkedIn shoutout sparked momentum

21:15 – Turning story and “being in the field” into inbound leads

28:27 – From political science to insurance sales to code

32:23 – The moment coding became “the thing”

33:53 – Building a sales pipeline for community partnerships

35:48 – Balancing a full-time job while building the org

43:06 – Why the name “Black Tech Philly” was intentional

44:57 – What “Do Small Business Like a Big Boss” means to Ian

46:06 – Where to find Black Tech Philly

🎤 About Our Guest

Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city.

Website: https://blacktechphilly.org

Ian on LinkedIn: linkedin.com/in/iank6

Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.

👉 Grab your assessment here: www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don't build it small.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed profitable systems, and created a business that delivers both financial success and work-life balance.

This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn't, and what every aspiring entrepreneur needs to hear.

🎧 What You'll Learn in This Episode:

How to leverage corporate experience to build credibility as an entrepreneur

The Bullseye Strategy for attracting ideal clients without limiting growth

A pricing framework to confidently raise your rates

How the TAGS Framework helps create a signature offer that stands out

Why your ideal client is often the person you were 5–10 years ago

⏱️ Episode Timestamps:

00:00 – Introduction

00:52 – Guest introduction: Shan Thomas

02:50 – From corporate career to entrepreneurship

08:34 – Overcoming challenges in a male-dominated industry

13:40 – Quitting without a plan and starting a business

19:36 – Faith, fear, and betting on yourself

25:00 – Profit strategy and revenue planning

27:08 – The Bullseye Strategy for client messaging

30:00 – The TAGS Framework

36:28 – Pricing with confidence

39:19 – Building the "10–4 Life"

42:41 – What "Do Small Business Like a Big Boss" means

44:24 – Wrap-up & calls to action

👤 About the Guest:

Shan Thomas is the founder of Credible Visibility Media, where she helps service-based business owners increase profitability through strategic positioning, signature offers, and scalable systems. Drawing from decades of Fortune 500 experience negotiating billion-dollar logistics contracts, Shan brings big-business strategies to small business owners. She is also the founder of Entrepreneur Her, an Atlanta-based community supporting women entrepreneurs.

Connect with Shan: LinkedIn — @shanthomasbiz

Ready to find out where your business is legally exposed?*

Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.

👉 Grab your assessment here: www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don't build it small.

If this episode helped you, don't forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Brad Stevens, founder and CEO of Outsource Access, to talk about knowing when it's time to outsource and how to build a team that helps your business grow.

Brad shares his entrepreneurial journey, the unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, mindset, and metrics that have fueled his rapid growth.

🎧 What You’ll Learn in This Episode:

• The two-question exercise to identify what you should outsource first
• How to view hiring as an investment instead of an expense
• Why Outsource Access serves businesses across 85 industries instead of specializing in one niche
• The key performance indicators Brad uses to measure outsourcing success
• How educational content and referrals helped grow the business without paid advertising
  

⏱️ Episode Timestamps
01:38 – Brad's origin story: renting Micro Machines toys in 4th grade
05:00 – Learning to spot problems worth solving
08:02 – The moment Brad knew entrepreneurship was the path
13:38 – How Brad thinks about building resilience
18:58 – The exploding pen disaster that led to Outsource Access
25:07 – Why Brad built his team in the Philippines
26:18 – Why Outsource Access serves 85 industries instead of niching down
29:49 – Building word-of-mouth marketing through content and education
33:45 – The two-question exercise for knowing what to outsource
40:14 – The 3 KPIs Brad watches most closely
44:27 – Brad's upcoming book, Automate and Delegate
48:38 – What "Do Small Business Like a Big Boss" means to Brad

🎤 About Our Guest
Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon.

🔗 Stay Connected with Sedgwick Andrews
👉 https://linktr.ee/Sedgwick_Andrews_LC

Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com

Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up.

Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies.

🎧 What You’ll Learn in This Episode:

• How Justin transitioned from corporate life to launching his own agency
• The realities of pricing professional services and avoiding undervaluing your work
• How Familiar Creatures evaluates potential clients using its “Smiley Face System”
• Why saying no to the wrong opportunities can accelerate long-term growth
• How small, agile teams can outperform much larger competitors

⏱️ Episode Timestamps:

• 00:03 – Introduction
• 01:10 – Leaving a six-figure salary
• 02:56 – Moving his family to start over
• 03:26 – Why Richmond became home for the business
• 07:09 – Landing the first anchor client
• 09:20 – The financial realities of early entrepreneurship
• 11:58 – Learning while building the business
• 13:52 – Pricing professional services
• 17:22 – Building a reputation over time
• 18:33 – Making decisions as business partners
• 21:47 – The creative process behind successful campaigns
• 26:06 – Scaling the agency from 2 to 10 people
• 29:30 – Choosing the right clients
• 30:23 – The “Smiley Face System” explained
• 33:23 – Why saying no can be the best business decision
• 37:57 – How small teams outperform big agencies
• 41:08 – What “Do Small Business Like a Big Boss” means to Justin
• 43:06 – Where to connect with Justin and Familiar Creatures

👤 About the Guest:
Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing.

Website: familiarcreatures.com
Instagram: @familiarcreatures

Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com

Stay Connected with Sedgwick Andrews:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don't build it small.

If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company.

This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth.

🎧 What You’ll Learn in This Episode:

Why recurring revenue is the foundation of a stable service-based business

How to decide whether to hire, outsource, or acquire to fill business gaps

The systems and software that transformed operations and job costing

How Doug and his wife successfully work together in the business

What every entrepreneur can learn from the landscaping industry's referral culture

⏱️ Episode Timestamps:

00:00 – Introduction

00:35 – Guest introduction: Doug Bonnell & True North Landscaping

01:17 – From automotive engineer to family business COO

03:03 – Taking the leap from corporate life

05:42 – Learning the business from the ground up

06:57 – Building recurring revenue through maintenance services

09:21 – Why recurring revenue matters

11:12 – Acquiring a competitor and expanding services

12:13 – Build, hire, or buy?

14:31 – Managing seasonality and workforce challenges

20:23 – Work-life balance as a business owner

23:43 – Running a business with your spouse

24:51 – Common mistakes customers make when hiring contractors

29:26 – Systems and technology that drive growth

32:12 – Advice for aspiring entrepreneurs

33:05 – What “Do Small Business Like a Big Boss” means to Doug

33:52 – Where to connect with Doug and True North Landscaping

👤 About the Guest:

Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal.

Connect with Doug:

LinkedIn: Doug Bonnell

Website: True North Landscaping

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:

📘 Free Guide: www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Myown Holmes, Owner and Senior Strategist of Socially Polished and Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and entrepreneurship.

Myown shares how she leveraged social media, strategic relationships, and community-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs.

🎧 What You’ll Learn in This Episode:

How the “Power of One” framework can help you grow without burnout

Why focusing on one platform can outperform trying to be everywhere at once

How to build a referral network and secure early testimonials through strategic partnerships

The government contracting opportunities many small business owners overlook

Why knowing your numbers and building the right advisory team is critical for growth

⏱️ Episode Timestamps:

00:04 – Welcome & guest introduction

01:04 – Building a business while raising a family

03:31 – The realities of building in the margins

07:25 – Knowing when it was time to leave her job

09:22 – Creating a structurally sound business

13:35 – Breaking into government contracting

16:12 – Diversifying revenue vs. stabilizing revenue

17:50 – The “always be marketing” mindset

18:57 – Knowing your numbers and building your dream team

22:38 – Finding the right platform for your audience

23:31 – The Power of One framework

26:04 – Organic marketing vs. paid advertising

31:10 – Building a referral network through bartering

35:59 – Using AI in small business

39:01 – The hardest lessons of entrepreneurship

40:26 – The mission behind The Prism Effect

46:22 – What “Do Small Business Like a Big Boss” means to Myown

48:22 – Where to connect with Myown

👤 About the Guest:

Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs.

Connect with Myown:

LinkedIn: https://www.linkedin.com/in/myownh/

Website: https://socially-polished.com/

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

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https://smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

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Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Cassel, co-founder and CTO of 4V Services, to talk about the realities of growing a consultancy, scaling a team, and building a business that doesn’t rely solely on referrals.

David shares the lessons he learned growing 4V Services from a small operation into a team of 18, the hard decisions that came with scaling back, and why every entrepreneur needs a real client acquisition strategy before growth becomes a problem.

🎧 What You’ll Learn in This Episode:

• How David evaluates business ideas using a 4-category framework
• Why relying only on referrals can become a major business risk
• How to identify skill gaps and decide whether to learn, hire, or outsource
• What it’s like building and running a business with your spouse
• What a fractional CTO does and how it helps growing businesses scale strategically
  

⏱️ Episode Timestamps:

• 00:14 – Welcome & guest introduction
• 00:35 – David’s origin story and launching 4V Services
• 04:06 – The 4-category framework for evaluating business ideas
• 08:56 – Landing early clients through referrals
• 10:21 – Understanding the MarkLogic niche
• 11:37 – Why referrals alone are a “time bomb”
• 16:17 – Scaling back and lessons on focus
• 18:40 – Strategic hiring and organic growth
• 22:28 – The challenge of training clients too well
• 24:35 – Balancing big clients and smaller accounts
• 26:04 – Running a business with your spouse
• 29:44 – The shift into fractional CTO services
• 36:28 – Advice David would give his younger self
• 38:01 – What “Do Small Business Like a Big Boss” means to David
  

👤 About the Guest:
David Cassel is the co-founder and CTO of 4V Services, a consultancy focused on helping enterprise organizations maximize their MarkLogic investments while applying operational strategy to software development. After nearly a decade at MarkLogic, David launched 4V Services with his wife and grew the business organically to a team of 18. He now helps businesses through fractional CTO services, providing executive-level technology leadership without the cost of a full-time hire.

Connect with David:

LinkedIn: David Cassel
Website: 4vservices.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Regnault Drake Sanders, founder of School Economy Inc., to talk about building an EdTech company from scratch with no outside funding.

Starting with just $2,000 in Amazon gift cards, Regnault built a platform that rewards K-12 students for academic engagement and now serves over 20,000 active students across New York, Atlanta, and Dallas. This conversation dives into validation, partnerships, grassroots growth, AI automation, and what it really takes to build a mission-driven business that also generates sustainable revenue.

🎧 What You’ll Learn in This Episode:

• How to validate a business idea before investors or partners
• Why non-technical founders need a technical ally
• How AI tools like Zapier and N8N streamline operations
• How major partnerships and relationships drive growth
• Building mission-driven revenue with repeatable sponsorships
  

⏱️ Episode Timestamps:
00:02 – Intro & guest welcome
01:25 – Origin of School Economy
03:20 – Mission behind the business
06:52 – How the platform works
09:25 – Referral & growth system
11:25 – Sponsorship ROI model
12:05 – Starting with $2,000
12:58 – Scaling to 20,000 users
16:16 – Building partnerships
17:40 – First 50 users via outreach
20:03 – Tech companies as people businesses
21:04 – Managing offshore dev teams
24:25 – Bootstrapping without VC
26:10 – Scaling with AI automation
27:47 – DIY PR & media coverage
32:08 – “Do Small Business Like a Big Boss”
33:04 – Where to connect

👤 About the Guest:
Regnault Drake Sanders is a serial entrepreneur and EdTech founder based in Atlanta, Georgia. He is the founder of School Economy Inc., a platform that rewards K-12 students for academic achievement with redeemable prizes and incentives. His platform has grown to serve 20,000 active students across multiple cities and has been featured on Fox 5 Atlanta and at Microsoft education events.

Connect with Regnault:
LinkedIn: linkedin.com/in/regnault-drake-sanders-24797310b

Website: schoolconomy.com

🚀 Ready to Make Your Business Official?

👉If you’ll be in Maryland on June 10, 2026, come see

Aisha in Columbia, MD:

https://www.eventbrite.com/e/1988791451769?aff=oddtdtcreator

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with George Ennis, founder of EAG Advertising, to talk about how small businesses can stop wasting money on marketing that doesn’t work and start building strategies that actually drive growth.

This conversation breaks down the biggest mistakes business owners make online, how to maximize a limited marketing budget, and why relationships—not just ad spend—are the real key to long-term business success.

🎧 What You’ll Learn in This Episode:

• How to audit your digital footprint and uncover hidden marketing issues
• The right way to calculate and prioritize your marketing budget
• Why pay-per-click advertising may not be the best move for small businesses
• The “presearch” method for building authentic LinkedIn relationships
• How small businesses can compete with bigger brands strategically
  

⏱️ Episode Timestamps:

• 00:01 – Welcome and guest introduction
• 00:52 – Twin dad life and George’s personal journey
• 01:53 – From corporate America to entrepreneurship
• 03:07 – Launching EAG Advertising
• 06:18 – The importance of niching down
• 08:59 – Building relationships that drive business
• 12:04 – LinkedIn outreach and the “presearch” strategy
• 15:54 – Common digital marketing mistakes
• 19:06 – Competing with big brands on a small budget
• 24:04 – Why websites still matter
• 28:37 – Growing and leading a team
• 33:20 – Work-life balance as an entrepreneur
• 37:49 – What “Do Small Business Like a Big Boss” means to George
• 41:20 – Where to connect with George and EAG Advertising
  

👤 About the Guest:
George Ennis is the Founder of EAG Advertising, a full-service marketing and advertising agency specializing in B2B, nonprofit, and complex industries. With more than 20 years of strategic agency experience, George helps small and mid-sized businesses create marketing strategies with big-business impact.

Connect with George:
LinkedIn: E.A.G. Advertising
Website: eagadvertising.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Joy L. King, founder of Lifestyles by Joy and Sweet Life Business Coaching, to talk about building intuitive, referral-based businesses while balancing a high-level executive role.

This conversation covers the real-life lessons behind starting messy, trusting your instincts, and creating a business rooted in relationships—what worked, what didn’t, and what every aspiring entrepreneur needs to hear.

🎧 What You’ll Learn in This Episode:

• How to stop chasing money and start building through relationships
• The “repeatable value” concept every founder must define before scaling
• How to protect and maintain your business while stepping into a corporate role
• Why mindset and self-worth are the biggest blockers to growth
• What to focus on in your first 30 days before investing in branding or assets

⏱️ Episode Timestamps:

• 00:00 – Introduction
• 00:46 – Guest introduction: Joy L. King
• 02:05 – Launching during the pandemic
• 06:29 – Turning design into therapy and purpose
• 09:21 – Building through referrals
• 11:42 – “All money ain’t good money”
• 17:34 – When chasing money backfires
• 24:14 – Tools and systems Joy uses
• 27:00 – Negotiating an executive role while keeping her businesses
• 33:31 – The #1 mindset block
• 38:15 – The first 30 days as a founder
• 44:14 – What “Big Boss” means

👤 About the Guest:
Joy L. King is a lifestyle architect, business coach, and executive. She is the founder of Lifestyles by Joy, a referral-based interior design firm, and Sweet Life Business Coaching, where she helps entrepreneurs define repeatable value and scale with intention. She also serves as a Chief at NCAN (National College Attainment Network), leading strategy and operations.

🔗 Connect with Joy:
lifestylesbyjoy.com
sweetlifebusinesscoaching.com
LinkedIn — linkedin.com/in/joyking912

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Jordie Kern, founder of 7 Eagle Group, to explore what it really takes to build and rebuild businesses from the ground up—seven times over.

Jordie shares his 35-year entrepreneurial journey, the mindset behind mission-driven business, and how a simple one-minute video is transforming how military veterans connect with meaningful careers.

This conversation dives deep into resilience, purpose, and practical business strategy, especially for founders building with limited resources but big vision.

🎧 What You’ll Learn in This Episode:

• How Jordie turned a mission to serve veterans into a 30-person recruiting company
• What the SkillBridge program is and how it supports both veterans and employers
• Why the traditional resume model is becoming outdated
• The most important hire to make when scaling a business
• How to think about funding without giving up equity
• Morning routines and time-blocking strategies from a serial entrepreneur
• Why your first business should be designed to fail safely and teach quickly

⏱️ Episode Timestamps:

• 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group
• 00:49 – Growing up as the son of a WWII Army veteran
• 04:21 – Early entrepreneurial ventures and working with the Clemente family
• 07:23 – The moment Jordie started 7 Eagle Group
• 10:06 – The reality of building the business from scratch
• 12:48 – How the SkillBridge program works
• 23:50 – The one-minute veteran video and why it works
• 30:15 – Scaling a remote team of 30+
• 34:50 – Bootstrapping vs. investors
• 36:35 – Systems, delegation, and protecting your genius zone
• 43:50 – Advice for mission-driven entrepreneurs
• 46:42 – What “Do Small Business Like a Big Boss” means to Jordie

👤 About the Guest:
Jordie Kern is the founder of 7 Eagle Group, a mission-driven talent platform based in Amherst, Massachusetts that connects military veterans and transitioning service members with meaningful civilian careers. With over 35 years of entrepreneurship experience and seven businesses built, Jordie has grown 7 Eagle Group into a fully remote team serving 125+ SkillBridge participants daily through its career academy. The company partners with major organizations including Amazon, the Kansas City Chiefs, American Airlines, and Jack Daniel’s.

Connect with Jordie:
Website: 7eagle.com
Email: [email protected]

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Stephen Spence, Managing Director and Co-Owner of Project MAPIT, to talk about his unconventional journey from a 20-year career in special education to building a thriving software company.

Stephen shares how a chance opportunity with a former student led him into the world of startups—without formal business training, funding, or a clear roadmap. From surviving on $37,000 in his first year to cold-walking contractor offices with zero sales experience, to now co-owning a company competing with teams 25x their size, Stephen breaks down the real lessons behind resilience, leadership, and growth.

🎧 What You’ll Learn in This Episode:

• How to keep going when you're left alone in a business and everything is on the line
• Why cold outreach often fails—and what actually works for lead generation
• How radical transparency builds trust and drives revenue
• Why you should master roles before delegating them
• What EBITDA is and why it matters for long-term business value
• How systems, tools, and AI support growth in modern businesses
• The mindset needed to handle rejection and stay in the game
  

⏱️ Episode Timestamps:

• 00:25 – Welcome & What is Project MAPIT
• 02:47 – From teacher to tech startup: Stephen's origin story
• 04:30 – When the founder left and Stephen stayed in the fight
• 07:24 – The family decision and support system
• 10:50 – Wearing every hat in the early years
• 13:30 – Lead generation: what worked and what didn’t
• 16:05 – Handling rejection in sales
• 18:00 – Learning roles before delegating
• 21:34 – Buying out a founder
• 23:53 – Understanding EBITDA
• 25:45 – Systems, tools, and AI
• 31:30 – AI in small business
• 33:06 – Advice for entrepreneurs
• 36:35 – What “Do Small Business Like a Big Boss” means to Stephen
• 38:30 – Where to find Stephen
  

👤 About the Guest:
Stephen Spence is the Managing Director and Co-Owner of Project MAPIT, an all-in-one mapping, reputation, and sales platform for contractors in the home services industry. A former special education teacher and coach, Stephen transitioned into entrepreneurship in his 40s and helped scale Project MAPIT into a competitive software company serving hundreds of clients.

Connect with Stephen:
Website: projectmapit.com
LinkedIn: Stephen Spence

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Stephen Conti, Founder and CEO of Tocar Spa, Tocar Sport, and Tocar Corporate Wellness. Stephen shares the remarkable story of how he went from running a small spa with Groupon deals to managing a multi-division wellness business in Howard County, Maryland. He reveals the real-life challenges, wins, and valuable lessons from his entrepreneurial journey, offering insights every aspiring entrepreneur can learn from.

🎧 What You’ll Learn in This Episode:

How Stephen transitioned from a marketing career to owning a thriving wellness business

The ups and downs of using Groupon as a launch strategy and what he would do differently

The importance of word-of-mouth referrals and leveraging networking through the Chamber of Commerce

How the Goldman Sachs 10,000 Small Businesses program helped accelerate his growth

The importance of hiring for cultural fit in a service-based business

How to scale a business without losing loyal clients, including transitioning them to other providers

⏱️ Episode Timestamps:

00:00 – Introduction

01:27 – Stephen’s life before Tocar Spa

07:17 – The side hustle: working at a massage franchise

09:27 – Early days of Tocar: no systems, just Groupon

11:20 – Networking: word-of-mouth & social media

14:47 – SCORE, Goldman Sachs, and finding the right CPA

17:18 – Funding the business and bootstrapping

18:35 – Identifying the revenue ceiling and scaling

20:27 – Hiring for culture fit

23:45 – Transitioning clients and leadership layers

32:40 – AI & robotic massage tech

40:35 – Advice to his younger self

45:14 – What Do Small Business Like a Big Boss means to Stephen

👤 About the Guest:

Stephen Conti is the Founder and CEO of Tocar Spa, Tocar Sport, and the newly launched Tocar Corporate Wellness, all located in the Columbia, Maryland area. Starting from a single treatment room and Groupon deals, Stephen has grown Tocar into a multi-division wellness company with 20+ team members across three business lines. He is also the creator of the Healing for Healers program, which provides free massages to caregivers of individuals with Alzheimer's, Parkinson's, and dementia.

Connect with Stephen:

Website: www.tocarspa.com

Location: 10630 Little Patuxent Parkway, Columbia, MD (by the mall) | Appointment only

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: Make Your Business Official

👉 Grab your FREE Legal Guide at:

Sedgwick Andrews Legal & Consulting

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, sits down with Bala Vishwanath, Founder and CEO of Novo Guild, to break down what it really takes to hire the right people in a startup.

Bala shares lessons from decades in entrepreneurship—from early startup failures to building a high-demand recruiting firm serving venture-backed companies. They discuss why hiring is harder than most founders expect, what makes a great early-stage hire, and how Lean principles and systems can improve hiring outcomes without losing the human element.

This conversation also explores the growing importance of go-to-market (GTM) talent and how immigration trends are impacting today’s tech talent pipeline.

• Why hiring is harder than most founders expect—and why great hires still fail
• What GTM talent is and why it’s critical for early-stage startups
• How to apply Lean principles and structured systems to hiring
• The key traits that predict success in startup environments
• How immigration trends are shaping the tech talent market

• 00:00 – Introduction & Novo Guild overview
• 01:08 – What GTM talent means
• 03:53 – Scaling a nonprofit globally
• 06:02 – From platform idea to recruiting firm
• 07:34 – Why hiring is harder than expected
• 10:46 – Building credibility with clients
• 12:20 – Applying Lean principles to hiring
• 17:29 – Using the scientific method in hiring
• 19:03 – Traits of successful startup hires
• 21:06 – Immigration and talent supply
• 23:04 – Work-life balance as a founder
• 24:13 – What “Big Boss” means to Bala

Bala Vishwanath is the Founder and CEO of Novo Guild, a talent firm helping venture-backed startups hire top engineering and go-to-market talent across the US and India. He previously founded United Prosperity, a nonprofit supporting small businesses through crowdsourced loan guarantees.

Connect with Bala Vishwanath:
Website: https://novoguild.com
Email: [email protected]
LinkedIn: Search “Bala Vishwanath”

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 https://www.igotnext.co/training

👉 Grab your FREE Legal Guide:
https://www.topemployermistakes.com

👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, sits down with Tonya Thomas, founder of Team Delegate, to discuss the entrepreneurial journey and the crucial skill of delegation.

Tonya shares her experiences transitioning from a solo entrepreneur to leading a successful virtual assistant agency. The conversation touches on the challenges of scaling a business, building trust with clients, and identifying when to hire a virtual assistant (VA) to manage overwhelm. They also discuss the tools and systems that can streamline task management and the value of working with US-based virtual assistants.

• Delegation is a learned skill—and it’s essential for business growth.
• Building trust with clients and VAs is key to a successful working relationship.
• How to know when it’s time to hire a virtual assistant to avoid burnout.
• Tools for effective task management and how they help in scaling a business.
• The importance of US-based virtual assistants and why they are a valuable asset to businesses.

• 00:00 – The entrepreneurial journey begins
• 03:10 – Navigating the early days of business
• 05:54 – Building Team Delegate: From solo to agency
• 09:05 – Transitioning from working in to working on
• 11:52 – Delegation: The art of letting go
• 15:08 – Identifying when to hire a virtual assistant
• 18:03 – Overcoming control issues in delegation
• 20:57 – Tools for effective task management
• 23:54 – Onboarding and building relationships with VAs
• 27:06 – Learning from mistakes and growing
• 30:01 – The value of US-based virtual assistants
• 32:57 – Finding fulfillment in helping others
• 35:58 – Staying grounded in entrepreneurship

• "Delegation is a skill set."
• "Communication is key."
• "Learn from your failures."
• "Identify when to hire a VA to manage overwhelm."
• "Trust is the foundation of client-VA relationships."

Tonya Thomas is the founder of Team Delegate, a virtual assistant agency offering US-based VAs to help businesses scale. Tonya’s entrepreneurial journey began in the early 2000s, and she now leads a growing agency focused on effective delegation, building trust, and supporting business owners as they grow their teams.

Connect with Tonya Thomas:
Website: teamdelegate.com
LinkedIn: linkedin.com/in/tonyathomas

Follow us for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share with another boss who needs to hear it.