Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)
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What Does “Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)” Talk About?
This episode of the James Dooley Podcast features a conversation between James Dooley and Craig Campbell on how to ask better questions when approaching successful entrepreneurs at conferences, networking events, and business meetups. The hosts break down why the most common question people ask, which is what niche to go into, is too vague and weak to generate a meaningful response. Instead, they argue that productive questions should focus on understanding one's own value, risk tolerance, and what skills or assets they can bring to a potential partnership.
James Dooley introduces the red car theory to illustrate how opportunity recognition is a trainable skill. Just as you only notice red cars once you start looking for them, business opportunities become visible only when you condition yourself to spot them. The hosts discuss how many of their own ventures, including James's safety surfaces company and Craig's AI growth partnerships, came through networking and leveraging other people's expertise rather than deliberate niche selection.
The episode also explores the difference between entrepreneur and intrapreneur thinking, with James suggesting this is actually one of the strongest questions someone can ask an experienced business owner. Craig shares how his AI business model, which builds out websites, social media, email, and automation infrastructure and then takes a percentage of growth, acts as a natural filter to identify people who are truly serious about investing in their own success.
“You ask a member of staff how many red cars they saw on the way into work today. They say they do not know. Then you say, Tomorrow, look out for every red car and count them. The next day they say, I saw 17 red cars. Then you explain that those red cars are opportunities they missed yesterday but saw today.”
— James Dooley
Who Are the Guests on “Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)”?
James Dooley is a serial entrepreneur and digital marketing expert based in the UK, known for building multiple businesses across different industries. He is recognised for his ability to identify market gaps and leverage the skills of business partners to create profitable ventures, as demonstrated by examples like his safety surfaces company and other ventures operating out of his PromoSEO office. James also creates content around entrepreneurship, including episodes on the advantages and disadvantages of starting a business.
Craig Campbell is an SEO consultant, speaker, and entrepreneur who has built a reputation in the digital marketing world through conferences, networking, and content creation. He has expanded into AI-driven business solutions, offering growth partnerships where he and his team build out automated business infrastructure including websites, social media, email, and virtual receptionists, and then earn a percentage of the business growth they help generate. Craig is known for spotting opportunities across multiple niches and applying transferable ideas from one market to another.
What Are the Key Takeaways From “Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)”?
Here are the key points discussed in this episode:
- Asking vague questions like what niche should I go into reveals a lack of self-awareness and is unlikely to generate useful guidance from experienced entrepreneurs.
- The red car theory demonstrates that opportunity recognition is a learnable skill, and training yourself to spot opportunities means you will begin seeing them everywhere in daily life.
- The most valuable questions to ask entrepreneurs focus on what you bring to the table, how you can monetise your skills, and who you can leverage rather than what market to enter.
- Understanding whether you are an entrepreneur or an intrapreneur is a powerful question that opens up deep conversation about risk appetite, desire for security, and personal goals.
- Many successful business ventures come from networking and putting yourself in the right rooms rather than sitting down and strategically selecting a niche to pursue.
“I never sat there deciding, I want to do this AI growth thing. The opportunity came to me because I was networking, travelling, speaking and putting myself out there.”
— Craig Campbell
Is “Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)” Worth Listening To?
This episode is worth listening to for anyone who has ever attended a business event and walked away feeling like they did not get much out of it. James and Craig give genuinely practical advice on how to show up to these events differently, shifting the focus from asking for answers to asking questions that spark real conversation. The red car theory segment alone is a memorable and actionable framework that listeners can apply immediately to change how they move through everyday environments.
What makes this episode particularly valuable is that both hosts speak from direct personal experience rather than theory. Craig's explanation of how his AI growth partnership model filters serious entrepreneurs from those who are not ready to invest is a concrete example of applied entrepreneurial thinking. James's discussion of the entrepreneur versus intrapreneur question gives listeners a tool they can use at their very next networking event. The episode is concise, honest, and packed with perspectives that challenge common assumptions about how business opportunities are found and created.
Who Should Listen to “Best Questions to Ask Successful Entrepreneurs (James Dooley Chats With Craig Campbell)”?
This episode is ideal for:
- Aspiring entrepreneurs who attend networking events or conferences but struggle to make meaningful connections or get useful advice from experienced business owners.
- Digital marketers and SEO professionals looking to move beyond client work into building or partnering on their own business ventures.
- Early-stage business owners who are unclear about whether they are better suited to running their own company or thriving within an existing business structure.
- Investors or growth-minded individuals interested in AI-driven business automation and partnership models that offer revenue sharing in exchange for infrastructure and expertise.
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What Are Listeners Saying About This Episode?
“The red car theory section genuinely changed how I think about spotting business opportunities. I have heard advice about networking before but James and Craig made it concrete and actionable. This is one of those episodes I will come back to.”
“I loved the breakdown of why asking what niche should I go into is such a weak question. Craig was blunt about it in the best way and the alternative framing around value, monetisation and skills is much more useful for anyone actually trying to build something.”
“The entrepreneur versus intrapreneur question is brilliant and I wish someone had asked me that years ago. It would have saved me a lot of wasted energy. Short episode but genuinely packed with useful perspective from two people who have actually built businesses.”
James Dooley and Craig Campbell discuss the best questions to ask entrepreneurs at conferences, networking events and business meetups. The conversation explains why asking better questions creates better opportunities because entrepreneurs respond to people who understand value, risk, leverage and what they bring to the table. James Dooley shares the red car theory to explain how business owners can train themselves to spot opportunities they previously missed. Craig Campbell explains why basic questions like “what niche should I go into?” are weak, and why stronger questions should focus on partnerships, monetisation, skills, opportunity spotting and risk appetite. They also discuss entrepreneur versus intrapreneur thinking, AI growth partnerships, business automation, marketing spend and how networking can create new ventures.
James Dooley: Questions to ask entrepreneurs. A lot of people attend entrepreneurship conferences, networking events and things like that.
If someone is starting out as a business owner, or they want to become an entrepreneur, what questions should they come up and ask to get the most out of you?
Craig Campbell: One question we always get is, “Why did you start that business in that niche?”
We spoke about it in a previous podcast. Why that niche? That is the biggest thing people ask me all the time. What niche should I go into? What should I do? For me, the marketing part is the easy part. But what business are you going to start? I am going to throw the question back to you first. You have more companies than me. I am not going to say what your companies are because I do not know if you want me to say it publicly. But the company where I have been in your office, with PromoSEO on the top floor and the other company there, what made you start that particular one? Was it other people’s skills and you using your marketing ability?
James Dooley: That was to do with the who, not the what.
The business partner’s dad had chopped up truck tyres and invented a way of using them. It just happened to be used for safety surfaces for kids. It was a very profitable market and there were not that many people doing it in the UK. I saw there was demand and I saw there were not many people doing it, so I knew there was profit margin there. From that, there was a domino effect. You start doing work in schools and colleges, then it leads into other products and services. I landed lucky in finding the business partner. You have got new ventures with AI coming along, and you have met amazing people over the years. They have now come to you with an idea and they are technical geniuses. You have managed to leverage their skills to take AI to another level with AI growth partnerships. That came from networking and leveraging those people. It was the same for me. Sometimes people ask entrepreneurs a question because they think they will get a magic answer to find the next niche. The honest answer is the red car theory. You ask a member of staff how many red cars they saw on the way into work today. They say they do not know. Then you say, “Tomorrow, look out for every red car and count them.” The next day they say, “I saw 17 red cars.” Then you explain that those red cars are opportunities they missed yesterday but saw today. Replace red cars with opportunities. Wherever you go, there are opportunities. It could be a billboard, a bus advert, someone walking past, a bar, or a networking event. The quiet person in the corner could be your next business partner or investor. I think asking questions at these events is the most important part. Some people are scared to go over and ask questions. What would you say to people who do not have the confidence to come over and ask you a question?
Craig Campbell: Do not ask basic 101 questions.
Do not ask, “What niche should I go into?” I could say sell anything. You can market anything, whether it is furniture, water, surfaces or anything else. That is the easy part. The real question is who can you leverage, how can you monetise it, and what can you bring to the table? With your business partners, they knew what they were doing, not many people were doing it, and there was profit in it. You had marketing skills and saw the opportunity. That conversation is much better than someone saying, “What niche should I get into?” I do not know you. I do not know what you know or what you do not know. You need to come with a better conversation. I can tell you stories about niches I went into, why I went into them, who I met through networking and how opportunities came about. But I never sat there deciding, “I want to do this AI growth thing.” The opportunity came to me because I was networking, travelling, speaking and putting myself out there. If you are a blank canvas, you have to create opportunities and learn to see opportunities. When people look at expired domains, they are seeing an opportunity. They might think, “I can leverage this and turn it into an affiliate website,” or use it to power up another website. That is the way you need to think. You need to spot opportunities. The red car theory is spot on. I think I am good at spotting opportunities because someone might tell me what they are doing and my brain starts thinking about how I can apply that somewhere else. I might not be interested in their niche, but I can use the same idea in another market. It is about return on investment. What can I bring to the table and what can the other person bring to the table? If there are two valuable things there, you can make money from it. It does not work if you go around asking someone to find a perfect business partner for you. You need to understand what you bring to the table as an entrepreneur. A lot of entrepreneurs do not even know what they have. They do not know marketing. They do not know how to do stuff.
James Dooley: I have a great question to ask an entrepreneur based on exactly what you are saying.
For anyone watching this, I strongly recommend checking out the link. We do a whole episode on entrepreneur versus intrapreneur. That is the question I would ask. If someone is uncertain and wants to ask an entrepreneur something, I would say, “How would you know whether it is right for me to be an entrepreneur or an intrapreneur?” When they ask that question, the entrepreneur will probably ask them several questions about who they are as a person. They might ask whether they want security, whether they are willing to take risks, and what kind of life they want. That helps the person understand the answer. If they want security and want someone else to take the risk for them, they are probably more of an intrapreneur. If they are willing to take risks and back themselves, they are more likely to be an entrepreneur. Asking, “Am I an entrepreneur or an intrapreneur?” opens up a lot of conversation. If someone came over to you and asked that, it would probably get your attention.
Craig Campbell: We actually have a solution for that with the AI business.
We can build someone a website, social media, email, texting, virtual receptionists and the whole setup. We can build a business like that. But are they prepared to put the marketing spend behind it? We can build and automate 99% of it, but they need to put the marketing spend in. That is why we want to go down the growth partner route. We can build the thing, they put the money in, and we take a percentage for doing it. That weeds out the people who are serious from the people who are not. For me, I would rather invest money to make more money. That is where entrepreneurship comes from. Years ago, I did not want to take risks and I wanted things to land in my lap. I am still waiting for that to happen. You need to decide what you are. If someone has big money or they are an investor or entrepreneur, we can build whatever they want. The rest is on them.
James Dooley: For sure.
Anyone watching this, make sure you check out the links about the advantages of entrepreneurship. We also do one on the disadvantages of entrepreneurship. If you are an entrepreneur watching this, what is the best question you have ever been asked? Maybe it put you in an uncomfortable position. I would love to know in the comments what the best questions are to ask an entrepreneur. Craig Campbell, it has been an absolute pleasure.
Craig Campbell: Cheers, mate.
Creators & Guests
Host
James Dooley is a UK entrepreneur.