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Managing one business is challenging enough, but handling several at once? Now that’s next-level. I should know — I’ve owned over 30 businesses in my lifetime, and as CEO, adding new ventures to our portfolio is practically a sport. Over the years, I’ve picked up plenty of strategies (and some wildly entertaining stories) that make balancing multiple businesses not just doable but honestly rewarding. Here’s my blueprint of what has really worked for me.

1. Time management is your superpower

Time is every entrepreneur’s most valuable asset. As someone managing multiple companies, I can’t stress enough how crucial it is to master your schedule. I assign dedicated blocks for each business or priority task — to illustrate, back when I was running my first duo of companies, I devoted mornings to one and afternoons and evenings to the other. This approach minimized distractions and helped me stay focused on what truly mattered each day.

I’m also a big believer in the 80/20 rule: focus on the 20% of activities that yield 80% of the results, and don’t be afraid to eliminate or delegate the rest. Technology can be a true lifesaver here — my digital calendar (and my handwritten one) keep me and my businesses moving at full speed.

Make the most of every free moment. I like to review emails, proposals or agreements while I’m cooking or eating. It’s a simple way to stay productive and avoid wasting time on tasks I can easily knock out during downtime. Every minute counts!

Related: How to Successfully Run Multiple Businesses

2. Delegate like a pro

No one’s a superhero — and you shouldn’t be expected to handle every task alone. I’ve learned the hard way that knowing what to hand off (and to whom) is critical. I concentrate on my strengths, like brainstorming and big-picture planning and leave specialized work to the pros.

Building teams of talented, trustworthy people is non-negotiable. If hiring full-time staff isn’t on the cards, there are skilled freelancers and virtual assistants just a few clicks away. One of my real estate marketing businesses requires a lot of content creation and marketing of luxury real estate homes in California. Outsourcing work like graphic design or video editing frees up my time to focus on growth initiatives.

3. Prioritize ruthlessly

Trying to juggle everything will only make you dizzy. That’s why prioritization remains one of my top skills. Every business I run gets its own set of goals, usually mapped out each quarter, and these guide my daily and weekly priorities. Not everything is urgent; knowing how to identify genuine emergencies versus issues that can wait is burnout prevention 101. And if a similar task pops up across several businesses — like a round of contract reviews or a big content-planning session — I tackle them together to maximize efficiency.

4. Get (and stay) organized

Organization is the thread holding this circus act together! For each venture, keeping communication, files and workflows in order — saving hours that would’ve otherwise been wasted hunting for that one lost document — is crucial. Documenting processes is also clutch; clear operations manuals empower my teams and simplify onboarding when it’s time to grow. Additionally, every Friday, I dedicate 30 minutes to decluttering my desk, cleaning out my inbox and closing open loops in my schedule. This process has saved my sanity more than once.

Related: Think You Can Handle Running Multiple Businesses? Here Are the Pros and Cons You Need to Consider.

5. Protect your work-life balance

Let’s be real: with multiple businesses, the temptation to work nonstop is strong, but burnout isn’t an option. I set firm boundaries. Although I love to work 24/7, I still take time to relax — usually, when my body says I have to. And I still make sure to pencil in downtime regularly, from daily exercise to mealtime and fun events.

I also try to work in business industries that I genuinely love. When I invest in hobby-based ventures, it never really feels like work. Let’s say you are a baseball card collector and you turned it into a business venture — you could attend card-collecting events and visit hobby shops as part of your workday. Blending passion with business keeps things exciting and fulfilling. These recharge moments fuel the energy and creativity I need for the week ahead. And, when those wins — big or small — come rolling in, I always take a breath to celebrate the progress. It’s a great morale boost that reminds me why I love the hustle.

6. Stay flexible and keep learning

If I’ve learned anything across my 30+ businesses, it’s that adaptability is a must. Every venture throws new curveballs and every mistake is another lesson in disguise. Sometimes, I would take on too much or get hung up on tasks I should have let go, but every stumble made me a better business owner. Keeping up with market trends, being open to pivots and investing in self-development — whether by attending conferences, coaching platforms, diving into leadership books or connecting with other entrepreneurs — makes me more effective and keeps my companies ahead of the curve.

Related: How Leaders Can Embrace Flexibility and Still Find the Productivity and Creativity They Need

7. Enjoy the ride

Juggling multiple businesses can feel like a high-wire act (and sometimes, it is), but with planning, the right team and an openness to learning, it’s absolutely possible — and incredibly rewarding. No entrepreneur starts as a master juggler. Skills build over time, and the satisfaction that comes from watching your business thrive is second to none. So, trust the process, enjoy your wins and go show the world just how much you can accomplish!

Whether you’re just starting or already deep into the entrepreneurial juggle, I hope these tips can help you make the most of your amazing adventure.

The right laptop isn’t just about specs — it’s about keeping your operations running smoothly wherever you are. This near-mint refurbished 13‑inch MacBook Pro from 2017 delivers reliable performance, pro‑level features, and the kind of portability that makes it easy to work from the office, client meetings, or the airport lounge.

Under the hood, the 3.1GHz dual‑core Intel Core i5 processor (with Turbo Boost up to 3.5GHz) and 8GB of RAM handle everything from financial modeling to presentation design without lag. The 512GB SSD offers fast load times and secure storage for critical business files, so you can access what you need instantly.

The 13.3‑inch Retina display keeps spreadsheets sharp and client presentations vivid, with 2560×1600 resolution and 500 nits of brightness. The Touch Bar streamlines your workflow with quick access to app‑specific tools, while Touch ID offers secure logins and quick Apple Pay transactions when booking travel or making purchases.

With four Thunderbolt 3 ports, you can connect to external displays for presentations, high‑speed storage drives for project backups, and even charge multiple devices at once. The backlit keyboard and Force Touch trackpad make typing and navigation comfortable and precise, whether you’re working late at night or on the move.

Weighing just over 3 pounds and encased in a durable aluminum chassis, this MacBook Pro is built for mobility without sacrificing performance. Wi‑Fi and Bluetooth connectivity keep you linked to your team and tools, no matter your location.

As a grade-A refurbished unit, it arrives in near‑mint condition with minimal to no cosmetic wear, giving you premium Apple hardware at a fraction of the cost — a smart investment for any professional looking to maximize value.

Equip yourself with a business‑ready MacBook Pro refurb with a Touch Bar for $324.97 (MSRP $1,499) and keep your work moving wherever opportunity takes you.

StackSocial prices subject to change.

After Microsoft CEO Satya Nadella posted on X that OpenAI’s GPT-5 service is included in Microsoft 365 Copilot, Copilot, GitHub Copilot, and Azure AI Foundry, competitor Elon Musk wasted no time predicting that “OpenAI is going to eat Microsoft alive.”

OpenAI is going to eat Microsoft alive

— Elon Musk (@elonmusk) August 7, 2025

OpenAI CEO Sam Altman brushed off Musk’s tweet during an appearance on CNBC’s “Squawk Box” on Friday with a short: “You know, I don’t think about him that much.”

Altman went on to note that previously, Musk had nothing but criticism for OpenAI.

“I thought he was just, like, tweeting all day [on X] about how much OpenAI sucks, and our model is bad, and, you know, [we’re] not gonna be a good company and all that,” Altman said.

Related: Elon Musk Says X Found the Vine Archive, Restoring Access

Nadella took a much more playful approach to Musk’s dire warning about Microsoft getting eaten alive, posting on X: “People have been trying for 50 years, and that’s the fun of it!”

People have been trying for 50 years and that’s the fun of it! Each day you learn something new, and innovate, partner, and compete. Excited for Grok 4 on Azure and looking forward to Grok 5!

— Satya Nadella (@satyanadella) August 7, 2025

This is far from the first time these two tech leaders have clashed. The two cofounded OpenAI in 2015, and Musk left in 2018 after a disagreement over the direction of the company’s mission.

Musk’s offer to acquire control of OpenAI for $97.4 billion was denied by Altman earlier this year, with Altman posting a snarky “No thank you, but we will buy Twitter for $9.74 billion if you want” note on social media.

Related: Sam Altman Says Elon Musk Is ‘Clearly a Bully’ Who Likes to Get in Fights with Rivals

^{Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success.}

Most entrepreneurs are still using AI like a basic assistant — plugging in prompts and hoping something sticks. But that’s not how today’s top creators are getting 50K views in 48 hours.

This video reveals how I used OpenAI’s brand-new ChatGPT Agent — a tool most entrepreneurs don’t even know exists — not for keyword research or guesswork, but to predict what to post next using real-time signals from Reddit, YouTube, and Substack.

The result? A viral video, top 2 media ranking, and a strategy you can replicate today.

What you’ll discover:

• The viral forecasting prompt I now run every Monday, so I never have to guess what to post again
• How to reverse-engineer your competitor’s entire funnel (without clicking their ads or hiring a consultant)
• The traffic play that helped me rank in Google’s AI-generated results in record time
• The secret to building a content calendar in 10 minutes flat — with emotional hooks and scroll-stopping titles that actually work

This isn’t just another AI hack. It’s a total shift in how smart solopreneurs are using ChatGPT’s new autonomous Agent to predict, build, and scale faster than most teams.

If you’re ready to build smarter, grow faster, and dominate your niche before everyone else catches on, this is the video to watch.

The AI Success Kit is available to download for free, along with a chapter from my new book, The Wolf is at The Door.

Last week, on Apple’s earnings call, CEO Tim Cook said he was looking to acquire companies.

“We’re very open to [mergers and acquisitions],” Cook said at the time. “We basically ask ourselves whether a company can help us accelerate a roadmap. If they do, then we’re interested.”

Related: She Was CEO of OpenAI for 2 Days. Now Her Secretive AI Startup Has Raised $12 Billion.

Cook noted that of the seven or so companies that Apple had acquired so far in 2025, several were not AI-focused and came from “all walks of life.” He also said the company was making deals fast — every few weeks.

^{Apple CEO Tim Cook BRENDAN SMIALOWSKI/AFP | Getty Images}

What is Apple looking for in a startup?

“We are not stuck on a certain size company,” Cook said.

Apple has about $133 billion of cash, so price isn’t the issue. Rather, the question would be how a startup can fit into the Apple ecosystem with consumer products.

Business Insider notes that Apple’s largest acquisition of all time was Beats Electronics in 2014 for $3 billion.

The outlet asked several experts in the field which companies Apple should consider buying, and many big names were thrown into the ring — including Perplexity, the popular AI-powered search engine.

Related: A Newly Acquired Startup Just Offered Its 200-Person Team a Choice — Work Weekends or Take a Buyout

Another notable suggestion was Thinking Machines Lab, the startup founded by former OpenAI CTO Mira Murati. The company has raised $12 billion so far, though it has yet to launch any products. In July, Murati posted on X that the company would be sharing its first product “in the next couple of months.”

Still, Perplexity and Thinking Machines Lab could be too pricey (both could end up costing somewhere close to $20 billion, BI estimates, if they were even for sale at all), so smaller companies definitely have a shot.

Maybe it’s time to give your pitch deck a refresh.

^{Join top CEOs, founders, and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue, and building sustainable success.}

When it comes to raising capital, too many startup founders chase investors before building something worth investing in. I’ve been on both sides of the conversation, as an entrepreneur raising funds and as an advisor helping founders position themselves for growth. The venture capital world doesn’t reward effort. It rewards traction, clarity and risk mitigation.

The good news? Making your startup attractive to VCs isn’t about smoke and mirrors. It’s about being strategic from day one.

Related: 4 Ways to Prepare to Raise Venture Capital

1. VCs don’t buy ideas — they buy momentum

Every founder thinks their idea is brilliant. But VCs don’t fund ideas. They fund execution.

If you haven’t tested the market, generated early traction or proven demand, you’re not building a startup — you’re writing a thesis.

Momentum could look like early revenue, an active waitlist, a successful beta rollout or even partnerships that validate the product’s relevance. You don’t need millions in the bank to show movement. You need signals that your idea works in the real world.

Too often, I see founders spending months on pitch decks and branding before speaking to a single customer. Flip that. Build, test, refine, then pitch.

2. Get obsessively clear on the problem you’re solving

VCs invest in problems, not just products. The bigger and more urgent the problem, the more compelling the opportunity.

One of the biggest red flags I see in startup decks is vague problem statements. “Our app makes life easier” isn’t compelling. “We reduce failed deliveries for ecommerce businesses by 30%” is.

I tell founders regularly that if a 10-second elevator pitch doesn’t make the investor’s eyebrows lift, you’re not close enough to the pain point.

Drill deep. Use data. Use emotion. Use lived experience. And then show how your product offers measurable relief.

3. Your team is half the pitch

At the early stage, VCs are betting more on people than products. That means your team, or at least your founding story, matters deeply.

I often ask, “Would I want to work for these people?” If the answer is no, why would someone want to back them?

What makes your team uniquely positioned to solve this problem? Is it domain expertise? Insider experience? Past success?

If your team looks like four college friends who thought up an app on a Friday night, that’s fine, but you need to prove you can execute like a seasoned unit. Highlight your operational discipline, your learning velocity and how you handle uncertainty together.

Related: What Venture Capitalists Look For When Investing In A Startup

4. Brand signals matter more than you think

This might sound odd coming from a founder of a digital PR company, but the truth is: Brand matters to VCs. A clean narrative, strong digital presence and earned media coverage all contribute to perceived credibility.

I’ve seen term sheets land faster for founders who looked investable online, even when the numbers were similar.

Investors are human. They Google you. They skim your LinkedIn. They check if you’ve been mentioned in relevant media or podcasts. Make sure what they find builds confidence, not confusion.

Invest early in your digital footprint. It doesn’t need to be perfect — it needs to be intentional.

5. Make it easy to say yes

VCs don’t just invest based on potential. They invest based on pattern recognition and risk management. Your job is to remove friction from the decision.

That means being transparent with your numbers, your roadmap and your current gaps. It means having your data room in order. It also means speaking the investor’s language.

I warn early-stage founders, “If your pitch sounds like an ad, not a strategy, you’re in trouble.”

Make it easy to see the opportunity, the upside and the plan for deploying capital wisely. The best founders don’t oversell. They clarify, document and invite collaboration.

6. VCs want to back founders, not fix them

One of the simplest and hardest truths in venture capital is this: VCs want to invest in people they trust to make good decisions without hand-holding.

That doesn’t mean you need to have all the answers. It means you need to have a learning mindset, the humility to take feedback and the strength to lead anyway.

I often look for founders who can be both teacher and student, confident in their vision, but curious enough to keep evolving.

In your pitch, show how you’ve adapted, improved and bounced back. VCs love grit, and they respect reflection.

Related: Seeking VC Funding? Make Sure You Have the Answers to These 5 Questions

Final thought: Think like an investor before you pitch one

The most investable founders are the ones who understand capital as a tool, not a trophy. They don’t pitch out of desperation. They pitch because they’ve done the work, built the momentum and are now ready to scale what already works.

Before you chase funding, build what a smart investor would want to buy into: clarity, traction, a credible team and a repeatable growth engine.

“A VC isn’t looking to rescue you — they’re looking to join you,” I remind every founder I mentor.

At the end of the day, you’re not just pitching a company. You’re inviting someone to help build it with you.

Make sure it’s a story worth joining.

Instagram unveiled its new “Instagram Map” feature this week, letting users share their most recent location when using the app. The feature is similar to Snapchat’s “Snap Map,” TechCrunch notes. Instagram had previously added location-sharing in November 2024, but it was for DMs only.

Of course, this has led to a flurry of posts on social media about safety issues. Meta told the New York Post in a statement that Instagram Map is “off by default, and your live location is never shared unless you choose to turn it on. If you do, only people you follow back—or a private, custom list you select—can see your location.”

Related: Instagram Is Paying Some Users Up to $20,000 to Bring New People to the Platform

Meanwhile, Head of Instagram Adam Mosseri posted on the app Thursday to clarify: “Quick Friend Map clarification: your location will only be shared if you decide to share it, and if you do, it can only [be] shared with a limited group of people you choose. To start, location sharing is completely off.”

“Personally, I use the map to share what I’m up to with a handful of my closest friends, and I curate that list carefully,” he wrote.

Still, some users posted in the comments that their location was on by default without knowing. Several Reddit threads have noted the same. Here’s how to make sure it’s off (if you prefer).

Related: Instagram’s CEO Says He ‘Experienced a Sophisticated Phishing Attack’ With Google

How to turn off your location on Instagram Map

• Go to your DM inbox, and select the “Map” circle next to “Notes.”
• Open the map view (you’ll see your friends who are sharing locations, whether yours is off or on).
• In the top right corner, select “Settings.”
• You’ll see a prompt: “Who can see your location?” and then select “No one.”
• Hit “Done” to save.

^{Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success.}

Take a closer look at “How to Train Your Dragon,” the live-action movie released in June. Embedded in the end credits of the movie is a warning: Universal Pictures, the major American film studio behind the film, will take legal action if any company or individual uses the film for AI training.

The end credit warning, which says that a movie “may not be used to train AI,” also appeared in “Jurassic World Rebirth,” released in July, and “The Bad Guys 2,” which came out in August, per The Hollywood Reporter.

Related: ‘Bottomless Pit of Plagiarism’: Disney, Universal File the First Major Hollywood Lawsuit Against an AI Startup

Alongside the message is a more standard one that states that the movie “is protected under the laws of the United States and other countries” and threatens “civil liability and criminal prosecution” if faced with “unauthorized duplication, distribution, or exhibition.”

Universal recently joined Walt Disney Pictures in taking legal action against an AI image-generating startup called Midjourney. In June, Disney and Universal filed a complaint accusing Midjourney of duplicating iconic characters from their copyrighted works in its AI outputs.

Midjourney made $300 million last year, partly by generating media containing copyrighted characters created by the studios, the complaint alleges. The document goes on to list characters like Hiccup from “How to Train Your Dragon” and Po from “Kung Fu Panda” as examples of Universal creations that Midjourney allegedly reproduced.

Related: Netflix Co-CEO Says the Company Used AI on a TV Show for the First Time: ‘Completed 10 Times Faster’

Universal Pictures generated $1.88 billion in box office revenue in the U.S. and Canada in 2024, a 3% decline from the previous year. Meanwhile, Disney was the top studio globally in 2024, bringing in $5.46 billion at the box office.

Instead of taking legal action against AI, other Big Eight film studios have begun to incorporate the technology into their movies. For example, Netflix disclosed last month that it used AI to generate footage for one of its shows for the first time. The Argentine science fiction show, “El Eternauta,” or “The Eternaut,” featured an AI-created scene showing a collapsing building.

Netflix claims to have completed the AI-generated scene “10 times faster” than if it had used standard tools.

^{Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success.}

OpenAI unveiled GPT-5 on Thursday, which the company is calling its “smartest, fastest, [and] most useful model yet.” In a press release, the company said the new model puts “expert-level intelligence in everyone’s hands” and is a “significant leap in intelligence over all our previous models.”

On Wednesday, OpenAI CEO Sam Altman called it a “major upgrade” and said that after the new model, using older versions felt “miserable.”

Related: OpenAI CEO Sam Altman Says AI Agents Are Like a Team of ‘Junior Employees’

In addition to improvements in coding, math, health, and other areas, the new GPT-5 also lets users choose a “personality” in settings. The default personality is still available and noted to be “clear, neutral, and adaptable.” Other options include “cynic” (sarcastic and dry, blunt but witty); “robot” (precise, emotionless, direct answers without extra words); “listener” (warm, laid-back, and calm with “light wit”); and “nerd” (playful, curious, celebrates knowledge and discovery).

And while previous reports highlighted the sycophancy of past models, OpenAI says that GPT‑5 “is less effusively agreeable” and “uses fewer unnecessary emojis.”

“It should feel less like ‘talking to AI’ and more like chatting with a helpful friend with PhD‑level intelligence,” the company wrote.

Related: Here’s What ‘Terrifies’ OpenAI’s CEO About Financial Institutions Today

GPT-5 is available for all users. OpenAI recommends these prompts to get started:

Create your own video game

• Create a single-page app in a single HTML file with the following requirements:
• Name: Jumping Ball Runner
• Goal: Jump over obstacles to survive as long as possible.
• Features: Increasing speed, high score tracking, retry button, and funny sounds for actions and events.
• The UI should be colorful, with parallax scrolling backgrounds.
• The characters should look cartoonish and be fun to watch.
• The game should be enjoyable for everyone.

Create your own drum simulator

• Create a single-page app in a single HTML file with the following requirements:
• Name: Virtual Drum Kit
• Goal: Play a drum kit using keyboard or clicks.
• Features: Multiple drum sounds, record and playback mode.
• The UI should be music-studio themed, polished, modern. Make it as beautiful as possible.

You can try GPT-5 free here.

Never have I been more grateful to be a business owner than when I recently caught up with a close friend and former colleague from my corporate days. This man is the definition of dependable. He’s hardworking, always prioritizing work and rarely complains or asks for anything.

Recently, he suffered a major hardship and needed to step back temporarily to focus on his family. Initially, his company was sympathetic and accommodating. In the end, however, he lost the job he had dedicated so much of his time and energy to.

Related: Winning Includes Putting People First in Your Business. This is How You Do It.

Corporations are not people…

As his friend, I am heartbroken. As a business owner, I am appalled. While I understand that businesses answer to their shareholders, what I struggle to reconcile is the decision to overlook loyalty and dedication of service for a minuscule amount of money. Learning how little regard the company had for my friend’s hardship only reaffirmed the promise I made when I started my company and vowed never to put profit before people.

Not long after my friend told me his story, one of my team members experienced a traumatic event. Instead of taking the “corporate” approach, citing policy, discussing FMLA and generally making a terrible situation more stressful, my business partner and I leaned in to support them. We made it clear that their well-being comes first. Never did it occur to either of us to let them go during a difficult time in their life because they couldn’t show up and make money for the company. My only thought was to help in any way I could.

…They’re only powered by people

The corporate world is famously unkind, but to find out that your years of service count for nothing at a time of personal hardship is nothing short of cruel. I am sure that had my friend been granted the flexibility he needed, he would have made it up to the company tenfold once he was able to return to work, but that can never happen because his company did not see it that way.

When team members know they will have support at work, especially during their most challenging moments, they are not just motivated; they are inspired. They will freely give you more of their time and attention, and they will care more about their work. Loyalty to your people breeds loyalty in return.

“Culture” and “assets”

What the corporate world has so tragically dismissed is the role of human kindness in cultivating human capital. Many large companies make a big deal about their team members being their most valuable asset, but what they really mean is that they value their team members for the revenue they generate.

As soon as that is no longer the case, they cut ties and find someone else to fill the spot. That kind of culture breeds resentment and fosters corruption because, when companies fail to protect their “most valuable asset,” those assets are less keen to protect the company.

Related: Why Kindness Is A Crucial Quality For Leaders

True human capital is measured in respect, not dollars

My people are my company. Without them, I would fail as an entrepreneur. I’ve worked hard to find the right people, train them, nurture their skills and create an environment that fosters creativity, because when they are happy, it shines through in their work. While this leadership style may not always be the most profitable in the short term, it has been a key factor in my company’s long-term success.

So, when something unexpected happens, I will be there to offer my support. My people know that, and I have every confidence that they would step up for me if ever I needed them to.