Ask a founder

Ask founders about starting, growing, and selling a company. Each one answers from their own essays, podcasts, and talks.

Updated

Brian Halligan

Co-founder and longtime CEO of HubSpot; now builds Sequoia's CEO practice

HubSpot co-founderHost of Long Strange Trip

Why themKnows the move from startup founder to scale-up CEO first-hand.

What is a good business to start?

The best business to start is one solving a real problem you actually understand, in a niche small enough to dominate and big enough to grow from. HubSpot began because we watched marketers struggling to interrupt people who were already tuning out.

How asking a founder on Delphi works

Each founder here has a Delphi, a Digital Mind built from their own essays, podcasts, talks, and posts. You ask in your own words, by text or voice, and it answers the way they would.

You'll find founders of software companies, franchises, media businesses, and venture funds. Ask the one who has done what you're trying to do.

  1. Pick a founder

    Start with someone who has worked on the problem you have.

  2. Ask in your own words

    Type or talk. Describe your situation the way you'd explain it to them in person.

  3. Keep going

    Ask follow-ups until you have what you need. You can try a few questions without an account, and sign in to keep your conversations.

Why Delphi is the best place to learn from founders

Real founders, in their own words
Every Delphi here is built from that person's own essays, podcasts, talks, and posts, and they decide what it covers.
Answers for your situation
Describe what you're dealing with, then keep asking follow-ups until the answer fits you.
Many voices on one question
See how the co-founder of HubSpot, the founder of Acquire.com, and a venture capitalist answer the same question.
Any time, text or voice
Ask at any hour, by typing or by talking, in more than 40 languages.

Questions people search for

Answered by people who've lived them.

What is a good business to start?

Start with a problem you already understand, ideally one you've had yourself. Most of these founders say your edge is what you already know: a customer base, a pain you've lived, or a market where incumbents have stopped improving. They differ on scale, from a lawn care business you can start with a truck to a tech company with a real moat.

  • Brian HalliganBrian HalliganCo-founder and longtime CEO of HubSpot; now builds Sequoia's CEO practice

    The best business to start is one solving a real problem you actually understand, in a niche small enough to dominate and big enough to grow from. HubSpot began because we watched marketers struggling to interrupt people who were already tuning out.

    Ask Brian a follow-up
  • Mike AndesMike AndesFounder of Augusta Lawn Care, Homeworks, and Mike Andes Media Group

    A simple home service business you can start with a truck and some tools: lawn care, cleaning, pressure washing, mobile detailing. I started mowing lawns at 11 because the barrier was low and the demand never went away. Pick one thing, price it right, and learn to sell it before you worry about scale.

    Ask Mike a follow-up
  • Cameron HeroldCameron HeroldFounder of the COO Alliance and former COO of 1-800-GOT-JUNK?

    I don't think there's a universal good business. The best one is the one where you already have unfair advantages: a customer base, a pain you've lived, or a model you can copy. I built 1-800-GOT-JUNK? because I understood franchise operations and the founder had a clear gap I could fill.

    Ask Cameron a follow-up

How do you start a business online?

Pick one specific problem and sell the fix to a handful of people before you build much. Several of these founders started with very little online: a blog and a spreadsheet, a simple website and cold outreach, or posts on Quora and Twitter. The tech stack can wait until someone has paid.

  • Brian HalliganBrian HalliganCo-founder and longtime CEO of HubSpot; now builds Sequoia's CEO practice

    Start with a problem you actually understand, ideally one you’ve felt yourself, and talk to potential users until the same pain shows up again and again. Then build the smallest thing that solves it, get it into their hands fast, and iterate based on what they do, not what they say.

    Ask Brian a follow-up
  • Anand SanwalAnand SanwalFounder of CB Insights, now co-founder of Forge Prep, a 6th to 12th grade school

    I started CB Insights with a blog and a spreadsheet, so my bias is to start small and start now. Pick one customer problem you can solve this week, build the smallest version, and charge before it feels ready.

    Ask Anand a follow-up
  • Andrew GazdeckiAndrew GazdeckiFounder and CEO of Acquire.com

    I started Bizness Apps with a simple website and a lot of cold outreach, because the only thing that actually validates a business is a customer willing to pay. Build the smallest version of your idea that solves one real problem, then go get your first paying customer before you worry about everything else.

    Ask Andrew a follow-up

How do you start a business with no money?

Sell before you spend. Most of these founders started with a service they could deliver themselves, got paid, and used that revenue to build what came next. Anand Sanwal funded CB Insights by selling subscriptions before the product existed.

  • Mike AndesMike AndesFounder of Augusta Lawn Care, Homeworks, and Mike Andes Media Group

    I started mowing lawns at 11 with my dad's push mower and a $20 ad in the church bulletin. If I had no money today, I'd knock doors, post in local Facebook groups, and offer the first job cheap or free in exchange for a review and three neighbor introductions. Revenue fixes almost every early problem; spend your time selling before you spend a dollar on branding.

    Ask Mike a follow-up
  • Anand SanwalAnand SanwalFounder of CB Insights, now co-founder of Forge Prep, a 6th to 12th grade school

    I started CB Insights with no outside funding by selling research subscriptions before we built the product, using customer cash to pay for the build. Find a problem people already pay to solve, get them to pay you to solve it, and let revenue fund the next step.

    Ask Anand a follow-up
  • Andrew GazdeckiAndrew GazdeckiFounder and CEO of Acquire.com

    I started Bizness Apps with basically nothing: a landing page, a fake buy button that 404'd, and $20 a day in ads to see if anyone would click. When they did, I built the thing.

    Ask Andrew a follow-up

How do you start a side hustle?

Pick the smallest thing you can sell now and put a price on it before it feels ready. Tiago Forte charged $5 for a workshop, Nicolas Cole wrote for free until someone paid, and Mike Andes did his first jobs almost free for reviews and referrals. Paying customers tell you whether it's worth growing.

  • Tiago ForteTiago ForteFounder of Forte Labs and author of Building a Second Brain

    I started Forte Labs as a side hustle while working other jobs, and the thing that made it real was charging $5 for a workshop before I felt ready. Pick the smallest version of what you can offer, put a price on it, and let paying customers teach you what actually matters.

    Ask Tiago a follow-up
  • Nicolas ColeNicolas ColeCo-founder of Ship 30 for 30 and Premium Ghostwriting Academy

    I started mine by accident. I was broke at 26, working a minimum-wage job, and began ghostwriting on the side for free until someone finally paid me. The whole game is picking one expensive problem you can already solve, proving you can deliver the result, then charging for outcomes instead of hours.

    Ask Nicolas a follow-up
  • Andrew GazdeckiAndrew GazdeckiFounder and CEO of Acquire.com

    I started both Bizness Apps and Acquire.com as side projects while I had other income, because keeping one foot in and one foot out let me experiment without betting everything.

    Ask Andrew a follow-up

How do you start a consulting business?

Sell what you already know to one narrow kind of client, and price it well from the start. Cameron Herold tripled his old hourly rate because only a third of his time would be billable. Several of them then turned what they learned into a repeatable process or a product.

  • Cameron HeroldCameron HeroldFounder of the COO Alliance and former COO of 1-800-GOT-JUNK?

    I started consulting in 1994 by selling what I already knew how to do, not by inventing something new. My first move was pricing: I figured out my old effective hourly rate, then tripled it because only a third of my time would actually be billable. Most new consultants undercharge and starve; charge like a premium service from day one and you will have the margin to market, deliver, and actually make money.

    Ask Cameron a follow-up
  • Nicolas ColeNicolas ColeCo-founder of Ship 30 for 30 and Premium Ghostwriting Academy

    I wouldn't start with consulting as the offer. I'd pick one problem I can solve, do free Loom audits for five prospects who look like my exact client, and turn the first paid engagement into a repeatable 5-step process. The whole game is making the service less custom every time.

    Ask Nicolas a follow-up
  • Anand SanwalAnand SanwalFounder of CB Insights, now co-founder of Forge Prep, a 6th to 12th grade school

    I started CB Insights after seeing data on private markets that nobody else was making useful, and my early consulting gigs came from people who wanted exactly that lens on their market. If I were starting one now, I'd pick a narrow problem I already understand better than the client, price by value not hours, and let the first few engagements shape the real offering.

    Ask Anand a follow-up

Who answers

All 11, in one list.

Questions

Can I ask about my own startup?

Yes. Describe your idea or your stage and ask follow-ups. Founders here cover fundraising, hiring, systems, writing, and selling a company.

What is a Delphi?

A Digital Mind built from a person's own words: their books, talks, interviews, posts, and podcasts. Ask it a question and it answers the way that founder would, based on what they've said.

Am I talking to the founder?

You're talking to their Delphi. Each founder chose to build it and decides what it covers, and it answers from their own material.

Is Delphi free?

Yes. Talking to any founder's Delphi is free, by text or voice.

How do I start?

Pick someone above and ask your question in your browser, by typing or talking. You can try a few questions without an account; sign in to keep your conversations.

Are my conversations private?

The person whose Delphi you talk to can see your conversations with it, so share only what you'd tell them. You can delete your account at any time and ask for a copy or deletion of your data.

Ask other people