If you've found your way into entrepreneurship, it doesn't matter if you come from a sales, product, creative or content background — you still need to figure out how to run the business efficiently.

I pose more than 150 questions that a founder or senior leader should constantly ask themselves - whether while starting a business or even while operating one. These range from thinking about product to finance to audience and distribution.

Starting with the Whys: This is the most existential question that you must ask before starting and once started, definitely keep it at the center of your actions. If you are still starting – think hard on why it makes sense for you to start a media/any business.

A) The Whys - 

1.     Why this, not that?

2.     Why you, not someone else?

3.     Why in this segment?

4.     Why will this succeed?

5.     Why are you an entrepreneur – the goal? Wealth, impact, self-improvement?

6.     Why should people work for you?

7.     Why should people give you money?

8.     Why should people trust you?

Close on the back of why come the Whats and the Whos: Keep things simple, yet difficult to copy with sharp eye on the audience, your own team, and your co-founders

B)  The Whats

1.     What problem are we solving?

2.     What other solutions exist out there?

3.     What will happen after the problem is solved?

4.     What will be the moat that protects our model?

5.     What do I need to know & measure?

6.     What will it cost / could possibly go wrong?

7.     What do I need to learn / management style?

8.     What do I need to communicate?

C) The Whos

1. Who is my audience?

2. Who is my competitor?

3. Who will give me money?

4. Who will sell this?

5. Who will be my business soulmate?

6. Who will I not please?

7. Who is my mentor / well-wisher?

8. Who are my most talented team members?

Next - The Wheres and the Whens will help you answer some of your initial whys. If you can figure out your market, its size, how the target can be reached, when will they / do they possibly need you the most and where do they expect to see you – it will dictate a lot of the product, distribution and positioning.

D) The Wheres

1. Where is my market & is it big enough?

2. Where does my TG hang out & is it easy to reach?

3. Where do I want to lead my audience?

4. Where will I find new things to do?

5. Where do I see my own self?

6. Where do I want to lead my business?

7. Where will I find good talent?

8. Where will I find the money?

E)  The Whens

1. When will my audience need this?

2. When is the right time to launch / expand?

3. When is the right time to for fund raise, partners, etc.?

4. When will my organization cease to be relevant?

5. When will my efforts to be successful?

6. When will I step back and only look at long-term?

7. When do I need external funding?

8. When should I move on from failed projects?

Finally, we must attempt to answer the all-important Hows – How will you do any of the things we have been discussing? Very importantly, how will your business make money and keep doing so? How will you maintain product and brand superiority? 

F)  The Hows

1. How will we launch / embark on something new?

2. How will we change audience behavior in our favor?

3. How will we make & manage the money?

4. How will we position ourselves?

5. How will I measure success?

6. How will I manage internal / external expectations?

7. How will I sustain differentiation / advantage?

8. How often do I need to break & reinvent?

However, while it is good to ask these questions, but how do you start your journey towards those answers. Therefore, it's time to discuss some of the Traits That Are Useful To Have.

A) Trait needed – Comfort with People

1. Can you sell?

2. Can you read the motivations of different sets of people? - employees, audience, clients

3. Can you hustle with investors, clients & vendors alike?

4. Do you recruit people like you or unlike you?

5. How often do you speak to your TG?

6. How do you manage feedback?

B)  Trait needed – Comfort with Ambiguity

1. Do you know the right data & where to get it?

2. Can you make inferences beyond the obvious?

3. Are you thinking 12-18 months ahead?

4. How often do the rules of business change?

5. How clear is the regulatory environment?

6. Do you react to competition’s moves & when?

7. How well do you manage the sales funnel & pipeline?

8. When will you receive revenues / funds?

C) Trait needed – Comfort with Numbers

1. Do you depend on someone else for data analysis?

2. Does your biz model use logical assumptions or gut feel?

3. Are you money savvy?

4. Can you craft a path to your goal using least variables?

5. How good are you at quantifying goals?

6. Do you know your cash cycle?

7. Do you know the success metrics of your segment?

8. Are you outcome focused or activity focused?

D) Trait needed – Passion; Not Emotion

1. Can you accept failures and move on?

2. Know that initial success doesn’t mean continued success?

3. Can you pivot, if need be?

4. Are your decisions supported by facts or emotion?

5. Are you passionate or emotional about the business?

6. Do employees, investors, other buy into the passion?

7. Does your brand convey the same passion?

8. Can your & your brand’s passion find you new audiences?

Thinking About Product

Now that we have covered these bases, what's next? The issue is not the technology. It’s aligning the people and workflows that allow the technology to deliver. And the steps you take to financially secure your organization.

While looking at a media business, content is king, but what keeps it on the throne is the audience, their needs, the way you distribute it, and the way consume it, engage with it, and maybe even co-create. This intermeshing of content with technology and audience and creating a pathway to repeated usage & monetization is product. And, in this aspect, the questions to ask are:

A) What is the product?

1. Is it only the content / journalism?

2. Is it the functionality / fancy things?

3. Is it the code that it runs on?

4. Can it scale & evolve?

5. What is the moat that you build?

6. Will it become irrelevant?

7. What are your sector benchmarks?

8. What are your internal products?

B)  How does it help the audience?

1. How does it solve needs of audience?

2. Is it easy to navigate?

3. Does the UI / UX invoke trust?

4. How do people discover it?

5. Will an audience brag about it?

6. Can you keep adding value?

7. Do you need to spend on acquisition?

8. How do you capture audience behavior?

C) How does it impact revenue?

1. Does it create trust & timely info?

2. Can it drive your brand positioning?

3. Does it make it easier / form habits?

4. Does it increase frequency & usage time?

5. Can you retain audience/upsell?

6. Is it easy to monetize traffic?

7. How easily can a subscriber pay for it?

D) What is the organizational structure?

1. How empowered is your product team?

2. Who is managing the data insights?

3. What are your internal processes?

4. Do all teams have a say?

5. Do the editorial, product, marketing & revenue heads understand each other?

6. What is the reporting structure?

7. What MIS, how frequently & what remedies?

Thinking About Money

And now, the beautiful world of finance, which I know many founders who come from content/creative backgrounds are uncomfortable with, but trust me, if you embrace it, you’ll see what a world of good it can do.

There are essentially two ways of funding a business – in one, you raise funds first, then spend on technology, R&D, marketing, IP, and then start monetizing those. In the other method, you start generating revenue from the start - you spend money on salaries and operating costs, and those resources in return get you revenue. In the first, you can achieve a large scale without worrying about your bills since someone has funded that part. In the second, you earn, you grow, little by little… in other words bootstrapping. But again, the questions to ask are important:

A) A business model that builds your Balance Sheet or your P&L?

1. Should you raise, spend first & earn later?

2. Should you earn first, grow slow & spend later?

3. What is your risk appetite & how networked are you?

4. What is your commitment horizon & what complexity can you manage?

5. Are you comfortable constantly hustling with investors? 

Other important questions in this money-oriented framework are:

B)  How to monetize?

1. How many rev streams can you explore?

2. Can you create habits / maximize touchpoints?

3. Are you commoditizing / overspecializing your sales?

4. How to keep sales funnel/pipeline full?

5. Can you find decent margin, high velocity?

6. Can you discover scope / structured products?

C) How to manage the $$?

1. Do you know your breakeven math?

2. Are your variable costs covered?

3. Can you manage cash flow, working cap cycle?

4. Can you collect receivables asap, even if you have to offer discounts?

5. Do you have a finance professional on the team or on retainer?

6. How do you manage the cash in bank?

7. Are you up to date with compliances?

D) How to raise funds?

1. When is the right time? How much?

2. Why? For cash or partner benefits?

3. Who do you approach and how?

4. What do investors want from you?

5. How much time does it take to raise?

Thinking About Audiences & Distribution

Of course, no discussion on media, or any B2C business, can be finished without addressing the audience and distribution. My presentation was not focused on these two aspects, since it was largely understood that "my audience for my product (aka presentation)" would already be aware of these two aspects. Nevertheless, I believe there is a framework around which we should approach these areas, and once again, you guessed it right, the framework involves asking questions:

A) Audience – the way to think about it

1. How do their needs change through the day?

2. When do they need you content?

3. How & where do they want it?

4. Why should they be loyal to you?

5. How do you become a habit in their lives?

6. Do they seek your content un-aided?

7. What kind of networks & devices are they on?

8. How much do they want to see and hear you?

9. How much do they want to be heard?

10. How engaged are they, and are you listening?

11. If you’re listening, are you acting on feedback?

12. Are you tracking what they are doing?

13. What is your North Star metric?

B)  Distribution – the way to think about it

1. Have you defined what success looks like?

2. Are you being conservative in your ideas?

3. Where, when, & how do audiences want it?

4. Do you have communities that interact on your platform?

5. Does distribution match your brand positioning?

6. Are newsletters or webinars good for you?

7. What social media is relevant for you?

8. Are your consumption pages optimized?

9. Will a bit of PR work better than paid posts?

10. Who can you collaborate with?

11. Where can you cross-promote?

    Finally, here is a link to the video