How do you build a tool that redefines the real estate game for agents and brokers? Today on the show, host Chad Pytel sits down with Chris Fellows, founder and CEO of Bold Street, to explore how his AI-powered platform is reshaping residential investment for real estate professionals. Originally focused on data analytics for big investors, Bold Street pivoted after the Great Recession to meet the needs of agents and brokers. Chris shares how the platform, developed over 18 months, helps agents master investor math and market analysis, boosting efficiency. The conversation dives into current market dynamics, like the rising costs of leads from platforms such as Zillow, which make Bold Street’s value proposition increasingly vital. Chris also expands on the company’s latest round of fundraising before sharing key lessons on scaling a startup in real estate. For these insights and more, don’t miss this fascinating conversation with Chris Fellows!

 Key Points From This Episode: A warm welcome to today’s guest, Chris Fellows, founder and CEO of Bold Street. Founding Bold Street: their initial AI strategy and how it has shifted. How their software helps agents and brokers be more efficient. Key takeaways from bringing their first product to market. Reflections on what could have helped the development process go more quickly. Chris and his team’s approach to sales and their general pricing model. A breakdown of their ideal customer and how they are reaching them. What they’ve done to address their ideal customers’ biggest objections. Unpacking current market dynamics, from expensive leads to class action lawsuits. How Bold Street brings value to the current real estate market. The benefits and challenges of running a business in such a disrupted market. Reflections on their current fundraising efforts versus their previous round. Lessons on scaling a startup both locally and through internet marketing. Links Mentioned in Today’s Episode: Chris Fellows on LinkedIn (https://www.linkedin.com/in/chriscfellows/)
 Chris Fellows' email (chris@boldstreet.ai) Bold Street (https://www.boldstreet.ai/) Chad Pytel on LinkedIn (https://www.linkedin.com/in/cpytel/) Chad Pytel on X (https://x.com/cpytel) thoughtbot (https://thoughtbot.com) thoughtbot on LinkedIn (https://www.linkedin.com/company/150727/) thoughtbot on X (https://twitter.com/thoughtbot) Giant Robots Smashing Into Other Giant Robots Podcast (https://podcast.thoughtbot.com/) Giant Robots Smashing Into Other Giant Robots Email (hosts@giantrobots.fm) Support Giant Robots Smashing Into Other Giant Robots (https://github.com/sponsors/thoughtbot)
How do you build a tool that redefines the real estate game for agents and brokers? Today on the show, host Chad Pytel sits down with Chris Fellows, founder and CEO of Bold Street, to explore how his AI-powered platform is reshaping residential investment for real estate professionals. Originally focused on data analytics for big investors, Bold Street pivoted after the Great Recession to meet the needs of agents and brokers. Chris shares how the platform, developed over 18 months, helps agents master investor math and market analysis, boosting efficiency. The conversation dives into current market dynamics, like the rising costs of leads from platforms such as Zillow, which make Bold Street’s value proposition increasingly vital. Chris also expands on the company’s latest round of fundraising before sharing key lessons on scaling a startup in real estate. For these insights and more, don’t miss this fascinating conversation with Chris Fellows!


Key Points From This Episode:
A warm welcome to today’s guest, Chris Fellows, founder and CEO of Bold Street.
Founding Bold Street: their initial AI strategy and how it has shifted.
How their software helps agents and brokers be more efficient.
Key takeaways from bringing their first product to market.
Reflections on what could have helped the development process go more quickly.
Chris and his team’s approach to sales and their general pricing model.
A breakdown of their ideal customer and how they are reaching them.
What they’ve done to address their ideal customers’ biggest objections.
Unpacking current market dynamics, from expensive leads to class action lawsuits.
How Bold Street brings value to the current real estate market.
The benefits and challenges of running a business in such a disrupted market.
Reflections on their current fundraising efforts versus their previous round.
Lessons on scaling a startup both locally and through internet marketing.
Links Mentioned in Today’s Episode:
Chris Fellows on LinkedIn

[Chris Fellows' email](chris@boldstreet.ai)
Bold Street
Chad Pytel on LinkedIn
Chad Pytel on X
thoughtbot
thoughtbot on LinkedIn
thoughtbot on X
Giant Robots Smashing Into Other Giant Robots Podcast
[Giant Robots Smashing Into Other Giant Robots Email](hosts@giantrobots.fm)
Support Giant Robots Smashing Into Other Giant Robots
How do you build a tool that redefines the real estate game for agents and brokers? Today on the show, host Chad Pytel sits down with Chris Fellows, founder and CEO of Bold Street, to explore how his AI-powered platform is reshaping residential investment for real estate professionals. Originally focused on data analytics for big investors, Bold Street pivoted after the Great Recession to meet the needs of agents and brokers. Chris shares how the platform, developed over 18 months, helps agents master investor math and market analysis, boosting efficiency. The conversation dives into current market dynamics, like the rising costs of leads from platforms such as Zillow, which make Bold Street’s value proposition increasingly vital. Chris also expands on the company’s latest round of fundraising before sharing key lessons on scaling a startup in real estate. For these insights and more, don’t miss this fascinating conversation with Chris Fellows!


Key Points From This Episode:
A warm welcome to today’s guest, Chris Fellows, founder and CEO of Bold Street.
Founding Bold Street: their initial AI strategy and how it has shifted.
How their software helps agents and brokers be more efficient.
Key takeaways from bringing their first product to market.
Reflections on what could have helped the development process go more quickly.
Chris and his team’s approach to sales and their general pricing model.
A breakdown of their ideal customer and how they are reaching them.
What they’ve done to address their ideal customers’ biggest objections.
Unpacking current market dynamics, from expensive leads to class action lawsuits.
How Bold Street brings value to the current real estate market.
The benefits and challenges of running a business in such a disrupted market.
Reflections on their current fundraising efforts versus their previous round.
Lessons on scaling a startup both locally and through internet marketing.
Links Mentioned in Today’s Episode:
Chris Fellows on LinkedIn

[Chris Fellows' email](chris@boldstreet.ai)
Bold Street
Chad Pytel on LinkedIn
Chad Pytel on X
thoughtbot
thoughtbot on LinkedIn
thoughtbot on X
Giant Robots Smashing Into Other Giant Robots Podcast
[Giant Robots Smashing Into Other Giant Robots Email](hosts@giantrobots.fm)
Support Giant Robots Smashing Into Other Giant Robots